EICOSANOIDS

All eicosanoids are prepared by published or proprietary procedures and are highly purified by various chromatographic methods. They are provided in their natural enantiomeric and free acid form unless indicated (? in which case they are offered as racemic mixtures. In a few cases the instability of the product precludes long term storage as the free acid. These products are provided as their methyl esters. They can be easily hydrolyzed to the acids using the procedure on page 000 of this catalog.

LEUKOTRIENES

EI-104
LTA₃
Leukotriene A₃ methyl ester
50 µg/ml hexane containing 2% triethylamine, 95-98% (remainder 11,12-trans isomer), MW=334.5, UVmax: 279 nm, (49,000) [83851-38-1] Storage: -80°C. Suicide inhibitor of LTA₄ hydrolase^1,2. Biosynthesis from Mead acid via 5-lipoxygenase³. For methyl ester hydrolysis procedure, see below.
50 µg
5 x 50 µg
1.0 mg

LA-004
LTA₄
Leukotriene A₄ methyl ester
50 µg/0.5 ml hexane containing 2% triethylamine, 95-98% (remainder 11,12-trans isomer), MW=332.5, UVmax: 279 nm (49,170)⁴ [72345-92-7] Structure - Scheme l, Storage: -80°C. Unstable intermediate in the biosynthesis of LTB₄ and LTC₄. The naturally occuring free acid is a substrate for LTA₄ hydrolase⁵ and LTC₄ synthase⁶ and plays a central role in transcellular leukotriene⁷ and lipoxin⁸ biosynthesis. Mobilizes Ca²⁺ in human neutrophils⁹. Supplied as the methyl ester for greater stability. For methyl ester hydrolysis procedure, see below.
50 µg
5 x 50 µg
1.0 mg

Hydrolysis Procedure for Leukotriene Methyl Esters

The methyl esters of leukotriene A₄ and other A series leukotrienes such as LTA₃ and LTA₅ may be hydrolyzed to the free acid as follows: The contents of one ampule (50 µg) is evaporated to dryness under a stream of argon or nitrogen. A solution (1 ml) of methanol, 50% sodium hydroxide (9:1) is added. After thorough mixing, the solution is allowed to stand at 4°C for 3 hours. The resulting highly alkaline (pH 13) solution of LTA₄·Na may be used in subsequent experiments. Decomposition is less than 10% over 7-10 days if stored at -80°C. A less alkaline solution may be prepared as follows: dilute the resulting solution from the above procedure with water (10 volumes). Apply to a reverse phase C-18 extraction cartridge (Sep-Pak^@ or other type). Wash with an additional 10 volumes of water and finally elute with methanol or ethanol (1ml). This provides an alcoholic solution of LTA₄·Na.

LB-003
LTB₃
Leukotriene B₃
50 µg/ml ethanol, >99%, MW=338.5, UVmax: 270 nm (50,000) [88099-35-8] Storage: -80°C. Minimally produced in essential fatty acid deficient states¹⁰. Less potent than LTB₄ with respect to PMNL aggregation and chemokinesis¹¹. Equipotent with respect to complement receptor enhancement and degranulation¹².
50 µg
5 x 50 µg
1.0 mg

LB-004
LTB₄
Leukotriene B₄
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 270 nm (50,000)¹³ [71160-24-2] Structure - Scheme l, Storage: -80°C. Stimulates leukocyte functions including chemokinesis¹⁴, chemotaxis¹⁵, lysosomal enzyme release¹⁶, superoxide anion production¹⁷, adhesion^18,19 and C3b receptor expression²⁰. Enhances activation, proliferation and differentiation of human B-lymphocytes²¹. Induces vascular permeability²², hyperalgesia²³, NK cell activity²⁴, and broncho-constriction²⁵. Effects are mediated via specific high and low affinity receptors²⁶. Assays: RIA²⁷, bioassay²⁸, HPLC²⁹, GCMS³⁰. Reviews: in inflammatory diseases^31-34 immunoregulation³⁵, biosynthesis⁵, SAR³⁶, general^6,37
50 µg
5 x 50 µg
1.0 mg

LB-005
LTB₅
Leukotriene B₅
50 µg/ml ethanol, >99%, MW=334.5, UVmax: 270 nm (50,000) [88763-92-2] Storage: -80°C. Biosynthesis from eicosapentaenoic acid³⁸. Lower affinity for the LTB₄ receptor³⁹ correlates with its 10- to 100-fold lower activity than LTB₄ with respect to leukocyte functional responses^40,41.
50 µg
5 x 50 µg

LC-004
LTC₄
Leukotriene C₄
50 µg/ml methanol/ammonium acetate buffer, 65:35 pH=5.6, >98%, MW=625.8, UVmax: 280 nm (49,000)⁴ [72025-60-6] Structure - Scheme 1, Storage: -80°C. Potent agonist for contraction of smooth muscle⁴². Induces microvascular permeability⁴³ and mucus secretion in airways⁴⁴. Enhances growth of human airway epithelial cells⁴⁵. Reduces myocardial contractility and coronary blood flow⁴⁶. Induces long lasting hypotension⁴⁷. Stimulates angiogenesis⁴⁸. Stimulates LH⁴⁹, LHRH⁵⁰ and prolactin⁵¹ release. Opens muscarinic potassium channels (I_K.ACh)⁵² and I_M channels⁵³. Produced in specific cell types or by transcellular biosynthesis^7,54. Rapidly metabolized to LTD₄ and LTE₄ in vivo⁵⁵. Assays: bioassay⁴⁷, HPLC⁵⁶, RIA⁵⁷, EIA⁵⁸, and GCMS^59,60. Reviews: in asthma^61-64 in ischemia and shock⁶⁵, in cardiovascular disease⁶⁶, in inflammation³², metabolism^55,67, general^6,33,67,69.
50 µg
5 x 50 µg
1.0 mg

LD-004
LTD₄
Leukotriene D₄
50 µg/ml methanol/ammonium acetate buffer, 70:30, pH=5.6, >98%, MW=496.7, UVmax: 280 nm (48,700)⁴ [73836-78-9] Structure - Scheme 1, Storage: -80°C. Potent agonist for contraction of smooth muscle⁴². Induces microvascular permeability⁴³ and mucus secretion in airways⁴⁴. Enhances growth of human airway epithelial cells⁴⁵. Reduces myocardial contractility and coronary blood flow⁴⁶. Induces long lasting hypotension⁴⁷. Biosynthesis from LTC₄ by g-glutamyltranspeptidase⁵⁵. Rapidly metabolized to LTE₄ in vivo⁵⁵. Assays: bioassay⁴⁷, HPLC⁵⁶, and GCMS^59,60. Reviews: in asthma^61,62,63,64in ischemia and shock⁶⁵, in cardiovascular disease⁶⁶, in inflammation³², metabolism^55,67, receptor signal transduction⁷⁰, general^6,33,68,69.
50 µg
5 x 50 µg
1.0 mg

LE-004
LTE₄
Leukotriene E₄
50 µg/ml methanol/ammonium acetate buffer 70:30, pH=5.6, >98%, MW=439.6, UVmax: 280 nm (49,400)⁴ [75715-89-8] Structure - Scheme 1, Storage: -80°C. Less potent than LTD₄ in smooth muscle contractile activity ⁴². Induces microvascular permeability⁴³ and mucus secretion in airways⁴⁴. Reduces myocardial contractility and coronary blood flow⁴⁷. Induces long lasting hypotension⁴⁷ and airway hyperresponsiveness⁷¹. Partial agonist at LTD₄ receptors⁷². Biosynthesis from LTD₄ by a dipeptidase⁷³. Metabolism via omega oxidation⁷⁴. Assays: bioassay⁴⁷, EIA⁵⁸, HPLC⁵⁶, and GCMS^59,60. Reviews: in asthma^61-64 in ischemia and shock⁶⁵, in cardiovascular disease⁶⁶, in inflammation³², metabolism^55,67, general^6,33,68,69.
50 µg
5 x 50 µg
1.0 mg

REFERENCES

1. J.F. Evans et al. J. Biol. Chem. 1985 160 10966

2. L. Orning et al. J. Biol. Chem. 1990 265 14911

3. B.A. Jakschik et al. J. Biol. Chem. 1983 258 12797

4. N. Cohen et al. J. Am. Chem. Soc. 1983 105 3661

5. B. Samuelsson and C.D. Funk J. Biol. Chem. 1989 264 19469

6. B. Samuelsson et al. Science 1987 237 1171

7. J. Maclouf et al. Pharmacol. Rev. 1989 21 1

8. S. Fiore and C.N. Serhan J. Exp. Med. 1990 172 1451

9. F. Luscinskas et al. Biochem. Pharmacol. 1990 39 355

10. J.B. Lefkowith et al. Prostagland. Leukotrienes Med. 1986 23 123

11. J. Evans et al. Prostaglandins 1985 30 981

12. T.H. Lee et al. Clin. Sci. 1988 74 467

13. E.J. Corey et al. J. Am. Chem. Soc. 1980 102 7984

14. A.W. Ford-Hutchinson et al. Nature 1980 286 264

15. E.J. Goetzl et al. J. Immunol. 1980 125 1789

16. H.J. Showell et al. J. Immunol. 1982 128 811

17. C.N. Serhan et al. Biochem. Biophys. Res. Commun. 1982 107 1006

18. S.-E. Dahlen et al. Proc. Natl. Acad. Sci. USA 1981 78 3887

19. P. Lindstrom et al. Scand. J. Immunol. 1990 31 737

20. L. Nagy et al. Clin. Exp. Immunol. 1982 47 541

21. K.A. Yamaoka et al. J. Immunol. 1989 143 1996

22. J. Raud et al. Proc. Natl. Acad. Sci. USA 1988 85 2315

23. H.A. Martin Brain Res. 1990 509 273

24. M. Rola-Pleszczynski et al. Transplant. Proc. 1986 18 44

25. P. Sirois et al. Prostagland. Leukotrienes Med. 1980 5 429

26. D.W. Goldman et al. Fed. Proc. 1987 46 200

27. F. Carey et al. Prostagland. Leukotrienes Med. 1986 22 57

28. M.N. Samhoun et al. Prostaglandins 1984 27 711

29. J.D. Escra et al. Anal. Biochem. 1986 154 332

30. W.R. Mathews Methods Enzymol. 1990 187 76

31. R.M. McMillan and S.J. Foster Agents Actions 1988 24 114

32. S.D. Brain and T.J. Williams Pharmacol. Ther. 1990 46 57

33. W. König et al. Eicosanoids 1990 3 1

34. A.W. Ford-Hutchinson Crit. Rev. Immunol. 1990 10 1

35. M. Rola-Pleszczynski J. Lipid Mediators 1989 1 149

36. R.E. Zipkin BIOMOL Res. News 1991 3 9

37. P. Borgeat and P.H. Naccache Clin. Biochem. 1990 23 459

38. S.M. Prescott J. Biol. Chem. 1984 259 7615

39. S. Charleson et al. Prostaglandins 1986 32 503

40. T. Terano et al. Prostaglandins 1984 27 217

41. T. Lee et al. J. Biol. Chem. 1984 259 2383

42. S.-E. Dahlen et al. Proc. Natl. Acad. Sci. USA 1983 80 1712

43. S.-E. Dahlen et al. Proc. Natl. Acad. Sci. USA 1981 78 3887

44. Z. Marom et al. Am. Rev. Resp. Dis. 1982 126 449

45. G.D. Leikauf et al. Amer. J. Physiol. 1990 259 L255

46. L.G. Letts and P.J. Piper Br. J. Pharmacol. 1982 76 169

47. J.M. Drazen et al. Proc. Natl. Acad. Sci. USA 1980 77 4354

48. T. Kanayasu.et al. Biochem. Biophys. Res. Commun. 1989 159 572

49. A.-L. Hulting et al. Proc. Natl. Acad. Sci. USA 1985 82 3834

50. M. Saadi et al. Life Sci. 1990 46 1857

51. C. Rougeot et al. Neuroendocrinol. 1990 51 267

52. R.W. Scherer and G.E. Breitwasser J. Gen. Physiol. 1990 96 735

53. P. Schweitzer et al. Nature 1990 346 464

54. S.J. Feinmark and P.J. Cannon J. Biol. Chem. 1986 261 16466

55. S. Hammarström et al. Mol. Cell Biochem. 1985 69 7

56. P. Borgeat et al. Methods Enzymol. 1990 187 98

57. E.C. Hayes et al. J. Immunol. 1983 131 429

58. P. Pradelles et al. Methods Enzymol. 1990 187 82

59. R.C. Murphy and A. Sala Methods Enzymol. 1990 187 90

60. C. Prakash et al. Prostaglandins 1989 37 251

61. H. Bisgaard Allergy 1984 39 413

62. S.-E. Dahlen et al. Adv. Prostagland. Thromboxane Leukotriene Res 1990 20 193

63. W.M. Abraham et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1990 20 201

64. C. Robinson and S.T. Holgate et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1990 20 209

65. A.M. Lefer Biochem. Pharmacol. 1986 35 123

66. G. Feuerstein Prostaglandins 1984 27 781

67. M. Huber et al. Eur. J. Biochem. 1990 194 309

68. P. Borgeat and P. Sirois J. Med. Chem. 1981 24 121

69. W.R. Henderson Am. Rev. Resp. Dis. 1987 135 1176

70. S.T. Crooke et al. Trends Pharmacol. Sci. 1989 10 103

71. J.P. Arm et al. Am. Rev. Resp. Dis. 1989 140 148

72. D.L. Saussy et al. J. Biol. Chem. 1989 264 19845

73. B.J. Campbell et al. Biochim. Biophys. Acta 1990 1042 107

74. A. Sala et al. J. Biol. Chem. 1990 265 21771

LEUKOTRIENE METABOLITES

CLB-004
20-COOH-LTB₄
20-Carboxy-leukotriene B₄
50 µg/ml ethanol, >99%, MW=366.5, UVmax: 270 nm (50,000) [80434-82-8] Structure - Scheme 2, Storage: -80°C. Biosynthesis by oxidation of 20-OH-LTB₄^1,2 via a 20-CHO-intermediate³. Further metabolized by ?oxidation⁴.
50 µg
5 x 50 µg
1.0 mg

HLB-004
20-OH-LTB₄
20-Hydroxy-leukotriene B₄
50 µg/ml ethanol, >99%, MW=352.5, UVmax: 270 nm (50,000) [79516-82-8] Structure - Scheme 2, Storage: -80°C. Primary LTB4 metabolite produced by omega oxidation in PMNL^1,2,5 retaining some chemotactic activity⁶. Omega oxidation is blocked by 17-ODYA (see Enzyme Inhibitors).
50 µg
5 x 50 µg
1.0 mg

DTR-512
6-trans-LTB₄
Metabolite of LTB₄ in rat kidney produced enzymatically by a novel isomerase reaction⁷.
See DiHETES

LEA-004
N-Ac-LTE₄
N-Acetyl leukotriene E₄
50 µg/ml methanol/ammonium acetate buffer 70:30, pH=5.6, >98%, MW=481.7, UVmax: 280 nm (49,400) [80115-95-3] Storage: -80°C. Major bilary metabolite of cysteinyl leukotrienes in the rat^8,9,10. Approximately 100-fold less active than LTC₄¹¹. Equiactive with LTE₄ in guinea pig lung parenchyma assay¹².
50 µg
5 x 50 µg

REFERENCES

1. S. Shak et al. J. Biol. Chem. 1984 259 10181

2. W.S. Powell J. Biol. Chem. 1984 259 3082

3. R.J. Soberman et al. J. Biol. Chem. 1988 263 7996

4. M.A. Shirley and R.C. Murphy J. Biol. Chem. 1990 265 16288

5. R.J. Soberman et al. Proc. Natl. Acad. Sci. USA 1985 82 2292

6. C.A. Dahinden et al. J. Immunol. 1984 133 1477

7. O. Breuer and S. Hammarström Biochem. Biophys. Res. Commun. 1987 142 667

8. W. Hagmann et al. FEBS Lett. 1985 180 309

9. C. Denzlinger et al. Science 1985 230 330

10. W. Hagmann et al. Prostaglandins 1986 31 239

11. A. Foster et al. Prostaglandins 1986 31 1077

12. M.N. Samhoun et al. Br. J. Pharmacol. 1989 98 1406

HYDROPEROXY-ACIDS

Hydroperoxyeicosatetraenoic acids (HPETEs) are prepared by the reaction of various lipoxygenases with arachidonic acid. The products are isolated and carefully purified by HPLC. Normal phase HPLC using hexane/2-propanol/acetic acid (991:8:l) is the recommended method¹ of purification and analysis of HPETEs. They may be stored at -80°C in organic solvents for months without decomposition but are rapidly metabolized in biologic milieu.

HP-125
15(S)-HPEDE
15(S)-Hydroperoxyeicosa-11Z,13E-dienoic acid
50 µg/ml ethanol, >98%, MW=340.5, UVmax: 234 nm (23,000), Storage: -80°C. Preferred hydroperoxide cofactor and stimulator of lipoxygenase activity that is not a substrate for the enzyme and does not comigrate with other HPETEs on HPLC².
50 µg
5 x 50 µg
1.0 mg

HP-005
5(S)-HPETE
5(S)-Hydroperoxyeicosa-6E,8Z,11Z,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=336.5, UVmax: 236 nm (23,000) [71774-08-8] Structure - Scheme 1, Storage: -80°C. Primary metabolite of arachidonic acid via the 5-lipoxygenase pathway. Intermediate in leukotriene biosynthesis³. Augments histamine release⁴. and calcium flux⁵.
50 µg
5 x 50 µg
1.0 mg

HP-012
12(S)-HPETE
12(S)-Hydroperoxyeicosa-5Z,8Z,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=336.5, UVmax: 237 nm (23,000) [71774-10-2] Structure - Scheme 3, Storage: -80°C. Primary metabolite of arachidonic acid via the 12-lipoxygenase pathway. Inhibits thromboxane synthase⁶. Inhibits platelet aggregation via activation of guanylate cyclase (100% at 5µM)⁷. Stimulates leukotriene biosynthesis⁸. Potent and selective inhibitor of Ca²⁺-calmodulin-dependent protein kinase II (IC₅₀=0.7µM)⁹.
50 µg
5 x 50 µg
1.0 mg

HP-515
15(S)-HPEPE
15(S)-Hydroperoxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid
50 µg/ml ethanol, >98%, MW=334.5, UVmax: 236 nm (23,000) [125992-60-1] Storage: -80°C. Primary metabolite of eicosapentaenoic acid via the 15-lipoxygenase pathway.
50 µg
5 x 50 µg

HP-015
15(S)-HPETE
15(S)-Hydroperoxyeicosa-5Z,8Z,11Z,13E-tetraenoic acid
50 µg/ml ethanol, >98%, MW=336.5, UVmax: 236 nm (23,000) [70981-96-3] Structure - Scheme 4, Storage: -80°C. Primary metabolite of arachidonic acid via the 15-lipoxygenase pathway. Inhibits prostacyclin synthesis¹⁰ and arachidonic acid induced platelet aggregation¹¹.
50 µg
5 x 50 µg
1.0 mg

For linoleic acid hydroperoxides

REFERENCES

1. N.A. Porter et al. J. Org. Chem. 1979 44 3177

2. C. Rouzer et al. J. Biol. Chem. 1988 263 10981

3. B. Samuelsson Science 1983 220 568

4. S.P. Peters et al. Nature 1981 292 455

5. P.H. Naccache et al. J. Clin. Invest. 1981 67 1584

6. S. Hammarström et al. Proc. Natl. Acad. Sci. USA 1977 74 3691

7. B. Brune et al. Mol. Pharmacol. 1991 39 671

8. J. Maclouf et al. Proc. Natl. Acad. Sci. USA 1982 76 6042

9. D. Piomelli et al. Proc. Natl. Acad. Sci. USA 1989 86 8550

10. S. Moncada et al. Prostaglandins 1976 12 715

11. D. Aharony et al. Thromb. Haemostasis 1981 46 265

HETES AND OTHER HYDROXY-ACIDS

H-215
15(S)-HEDE
15(S)-Hydroxyeicosa-11Z,13E-dienoic acid
50 µg/ml ethanol, >99%, MW=324.5, UVmax: 234 nm (23,000), Storage: -20°C. Identified in psoriatic skin scale extracts (15-OH stereochemistry, however was not determined)¹. Inhibits 5-lipoxygenase (IC₅₀=26 µM)².
50 µg
5 x 50 µg

HR-505
(?5-HEPE
(?5-Hydroxyeicosa-6E,8Z,11Z,14Z,17Z-pentaenoic acid
50 µg/ml ethanol, >98%, MW=318.5, UVmax: 236 nm (23,000)³, Storage: -20°C. Racemic chromatographic reference standard.
50 µg
5 x 50 µg

HR-005
(?5-HETE
(?5-Hydroxyeicosa-6E,8Z,11Z,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=320.5, UVmax: 236 nm (23,000)^3,4, Structure - Scheme 1, Storage: -20°C. Biosynthesis via rat hepatic microsomal cytochrome P-450^5,6. Racemic chromatographic reference standard.
50 µg
5 x 50 µg
1.0 mg

H-005
5(S)-HETE
5(S)-Hydroxyeicosa-6E,8Z,11Z,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=320.5, UVmax: 236 nm (23,000)^3,4 [70608-72-9] Structure - Scheme 1, Storage: -20°C. Biosynthesis via 5-lipoxygenase⁷. Chemotactic⁸ and chemokinetic⁹ for PMNL. Induces degranulation¹⁰, and calcium flux¹¹. Augments islet cell insulin release¹². Inhibits granulocyte¹³ and smooth muscle cell proliferation¹⁴. Metabolized by omega oxidation¹⁵. Receptors¹⁶. Assays: HPLC¹⁷, TLC¹⁸, GCMS¹⁹. Review²⁰.
50 µg
5 x 50 µg
1.0 mg

HL-005
(?5-HETE lactone
50 µg/ml ethanol, >98%, MW=302.5, UVmax: 236 nm (23,000)³ [73279-37-5] Structure - Scheme 1, Storage: -20°C. Unique marker for 5-lipoxygenase activation²¹. Inhibits 5-lipoxygenase (IC₅₀=27 µM)²².
50 µg
5 x 50 µg
1.0 mg

H-305
(?5-HETrE
(?5-Hydroxyeicosa-6E,8Z,11Z-trienoic acid
50 µg/ml ethanol, >98%, MW=322.5, UVmax: 236 nm (23,000)³ [88053-46-7] Storage: -20°C. Racemic chromatographic reference standard. Biosynthesis (5(S)-isomer) in RBL cells from Mead acid via 5-lipoxygenase²³.
50 µg
5 x 50 µg

H-008
8(S)-HETE
8(S)-Hydroxyeicosa-5Z,9E,11Z,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=320.5, UVmax: 237 nm (23,000)³, [98462-03-4] Storage: -20°C. Biosynthesis in human neutrophils²⁴, phorbol ester-treated mouse epidermis²⁵ and by hepatic microsomal cytochrome P-450⁶. Chemotactic for neutrophils²⁶.
50 µg
5 x 50 µg

H-009
9(S)-HETE
9(S)-Hydroxyeicosa-5Z,7E,11Z,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=320.5, UVmax: 235 nm (23,000)³ [79495-85-5] Storage: -20°C. Identification in human neutrophils²⁴ and in psoriatic skin²⁷.
50 µg
5 x 50 µg

H-011
11(S)-HETE
11(S)-Hydroxyeicosa-5Z,8Z,12E,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=320.5, UVmax: 235 nm (23,000)³ [54886-50-9] Storage: -20°C. Biosynthesis in rat mast cells²⁸ and VX₂ carcinoma cells²⁹. 11(R)-isomer is produced via cyclooxygenase³⁰.
50 µg
5 x 50 µg

HR-012
(?12-HETE
(?12-Hydroxyeicosa-5Z,8Z,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >99%, MW=320.5, UVmax: 237 nm (23,000)³ Storage: -20°C. Racemic chromatographic reference standard.
50 µg
5 x 50 µg

H-112
12(R)-HETE
12(R)-Hydroxyeicosa-5Z,8Z,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >99%, MW=320.5, UVmax: 237 nm (23,000)³ [82337-46-0] Structure - Scheme 5, Storage: -20°C. Biosynthesis in psoriatic skin and corneal epithelial cells via cytochrome P-450³². More potent than 12(S)-HETE in inducing human leukocyte chemokinesis³³ and aggregation³⁴. Proinflammatory effects in human skin³⁵. Inhibits renal, cardiac and corneal Na⁺,K⁺-ATPase³⁶. Reduces intraocular pressure³⁷. Stereochemical analysis by chiral phase HPLC³⁸. Review³⁹.
50 µg
5 x 50 µg
1.0 mg

H-012
12(S)-HETE
12(S)-Hydroxyeicosa-5Z,8Z,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=320.5, UVmax: 237 nm (23,000)^3,4 [54397-83-0] Structure - Scheme 3, Storage: -20°C. Biosynthesis by platelet 12-lipoxygen ase⁴⁰. Chemotactic and chemokinetic for PMNL⁴¹ and for vascular smooth muscle cells⁴². Antiproliferative effect on smooth muscle cells⁴³. Second messenger in angiotensin induced aldosterone production⁴⁴. Induces endothelial cell retraction and tumor cell adhesion⁴⁵. Regulates platelet activation⁴⁶. Induces heat shock proteins in human leukocytes⁴⁷. Metabolized via omega oxidation⁴⁸, ?oxidation and reductase⁵⁰ pathways. Assays: RIA^51,54, HPLC¹⁷, TLC¹⁸, GCMS¹⁹. Reviews^20,39.
50 µg
5 x 50 µg
1.0 mg

H-312
Tetranor-12(R)-HETE
8(R)-Hydroxy-4Z, 6E, 10Z-hexadecatrienoic acid
50 µg/ml ethanol, >98%, MW=266.4, UVmax: 237 nm (23,000) Storage: -20°C
A biologically active metabolite of 12(R)-HETE in corneal tissue⁵². Induces corneal swelling⁵³.
50 µg
5 x 50 µg

HRT-012
12(S)-HHT
12(S)-Hydroxyheptadeca-5Z,8E,10E-trienoic acid
See Prostaglandin Metabolites

H-515
15(S)-HEPE
15(S)-Hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid
50µg/ml ethanol, >98%, MW=318.5, UVmax: 236 nm (23,000)³ [86282-92-0] Storage: -20°C. Biosynthesis from eicosapentaenoic acid via 15-lipoxygenase.
50 µg
5 x 50 µg

H-015
15(S)-HETE
15(S)-Hydroxyeicosa-5Z,8Z,11Z,13E-tetraenoic acid
50 µg/ml ethanol, >99%, MW=320.5, UVmax: 236 nm (23,000)^3,4 [54845-95-3] Structure - Scheme 4, Storage: -20°C. Biosynthesis in human neutrophils⁵⁴, platelets⁵⁵, eosinophils⁵⁶ and reticulocytes⁵⁷. Most abundant eicosanoid in human bronchi⁵⁸. Regulates T lymphocyte mitogenesis⁵⁹. Induces immunosupression⁶⁰. Stimulates migration of capillary endothelial cells and neovascularization⁶¹. Supresses renin production⁶². Inhibits ACTH stimulated corticosterone production⁶³. Inhibits 5-LO⁶⁴ and 12-LO⁶⁵. Metabolized via 5-lipoxygenase⁶⁶, dehydrogenase⁶⁷, omega-⁶⁸ and ?oxidation pathways⁶⁹. Assays: RIA⁷⁰, HPLC¹⁷, TLC¹⁸, GCMS¹⁹. Review²⁰.
50 µg
5 x 50 µg
1.0 mg

H-315
15(S)-HETrE
15(S)-Hydroxyeicosa-8Z,llZ,13E-trienoic acid
50 µg/ml ethanol, >99%, MW=322.5, UVmax: 236 nm (23,000)³ [13222-49-6] Storage: -20°C. Biosynthesis from dihomo-g-linolenic acid in human platelets⁷¹ and mouse peritoneal macrophages⁷². Induces a concentration dependent inhibition or potentiation of platelet aggregation⁷¹. Anti-inflammatory, inhibits 5-LO^72,73 and 12-LO⁷³.
50 µg
5 x 50 µg
1.0 mg

REFERENCES

1. R.D.R. Camp et al. Prostaglandins 1983 26 431

2. F. Haviv et al. J. Med. Chem. 1987 30 254

3. M.J. Gibian et al. Anal. Biochem. 1987 163 343

4. C.D. Ingram and A.R. Brash Lipids 1988 23 340

5. J.R. Falck et al. Tetrahedron Lett. 1984 25 1475

6. J. Capdevila et al. Biochem. Biophys. Res. Commun. 1986 141 1007

7. P. Borgeat et al. J. Biol. Chem. 1976 251 7816

8. E.J. Goetzl et al. Immunology 1980 34 491

9. R.M.J. Palmer et al. Prostaglandins 1980 20 411

10. G.M. Bokoch and P.W. Reed J. Biol. Chem. 1981 256 5317

11. J.T. O'Flaherty and J. Nishihira Biochem. Biophys. Res. Commun. 1986 148 575

12. S.G. Laychock Endocrinology 1985 117 1011

13. W. Dodge et al. Biochem. Biophys. Res. Commun. 1985 131 731

14. D.L. Smith et al. Prostagland. Leukotrienes Med. 1984 16 1

15. .T. O'Flaherty et al. J. Immunol. 1986 137 3277

16. J.T. O'Flaherty et al. J. Biol. Chem. 1993 268 14708

17. J.M. Boeynaems et al. Anal. Biochem. 1980 104 259

18. J.A. Salmon et al. Methods Enzymol. 1978 86 477

19. R.W. Walenga et al. Prostaglandins 1987 34 733

20. A.A. Spector et al. Prog. Lipid Res. 1988 27 271

21. J.M. Schröder et al. Proceedings, 6th Int. Conf. on Prostaglandins and Related Compounds, Florence, Italy, 1986, p. 438

22. F. Kerdesky et al. J. Med. Chem. 1987 30 1177

23. B.A. Jakschik et al. J. Biol. Chem. 1983 258 12797

24. E.J. Goetzl et al. J. Exp. Med. 1979 150 406

25. G. Fürstenberger et al. J. Biol. Chem. 1991 266 15738

26. E.J. Goetzl et al. Biochem. Biophys. Res. Commun. 1981 101 344

27. R.D. Camp et al. Prostaglandins 1983 26 431

28. L.J. Roberts et al. Prostaglandins 1978 15 717

29. W.C. Hubbard et al. Prostaglandins 1978 15 721

30. B.N.Y. Setty et al. Biochim. Biophys. Acta. 1985 833 484

31. P.M. Woolard Biochem. Biophys. Res. Comm. 1986 136 169

32. M.L. Schwartzman et al. Proc. Natl. Acad. Sci. USA 1987 84 8125

33. B. Fruteau deLaclos et al. Prostaglandins 1987 33 315

34. J.F. Evans et al. Biochim. Biophys. Acta. 1987 917 406

35. P.M. Woolard et al. Br. J. Dermatol. 1988 118 277

36. J.L. Masferrer et al. Biochem. Pharmacol. 1990 39 1971

37. J.L. Masferrer et al. Invest. Ophthalmol. Vis. Sci. 1990 31 535

38. D.J. Hawkins et al. J. Biol. Chem. 1987 262 7629

39. D.J. Fretland and S.W. Djuric Prostagland. Leukotrienes Essent. Fatty Acids 1989 38 215

40. M. Hamberg et al. Proc. Natl. Acad. Sci. USA 1974 71 3400

41. E.J. Goetzl et al. J. Clin. Invest. 1977 59 179

42. J. Nakao et al. Atherosclerosis 1982 44 339

43. D.L. Smith et al. Prostagland. Leukotrienes Med. 1984 16 1

44. J.L. Nadler et al. J. Clin. Invest. 1987 80 1763

45. K.V. Honn et al. FASEB J. 1989 3 2285

46. F.Sekiya et al. Biochem. Biophys. Res. Commun. 1991 179 345

47. M. Köller and W. König Biochem. Biophys. Res. Commun. 1991 175 804

48. A.J. Marcus et al. J. Biol. Chem. 1988 263 2223

49. S.N. Mathur et al. J. Biol. Chem. 1990 265 21048

50. S.L. Wainwright and W.S Powell J. Biol. Chem. 1991 266 20899

51. L. Levine et al. Prostaglandins 1980 20 923

52. M. Nishimura et al. Arch. Biochem. Biophys. 1991 290 326

53. W.D. Woods et al. Invest. Ophthalmol. Vis. Sci. 1995 36 S138

54. P. Borgeat et al. Proc. Natl. Acad. Sci. USA 1979 76 2148

55. P. Wong et al. J. Biol. Chem. 1985 260 9162

56. J. Turk et al. J. Biol. Chem. 1982 257 7068

57. R. Bryant et al. J. Biol. Chem. 1982 257 6050

58. M. Kumlin et al. Arch. Biochem. Biophys. 1990 282 254

59. J.M. Bailey et al. Cell Immunol. 1982 67 112

60. J.C. Aldiger et al. Prostagland. Leukotrienes Med. 1984 13 99

61. J.E. Graeber et al. Prostaglandins 1990 39 665

62. I. Antonipillai et al. Hypertension 1987 10 61

63. D.B. Jones et al. J. Endocrinol. 1987 112 253

64. J.Y. Vanderhoek et al. J. Biol. Chem. 1980 255 10064

65. J.Y. Vanderhoek et al. J. Biol. Chem. 1980 255 5996

66. N. Serhan et al. Proc. Natl. Acad. Sci. USA 1986 83 1983

67. M. Bergholte et al. Arch. Biochem. Biophys. 1987 257 444

68. R. Okita et al. Mol. Pharmacol. 1987 32 706

69. X.-Y. Shen et al. Biochemistry USA 1988 27 996

70. R. Bryant et al. Prostaglandins 1983 26 375

71. M. Guichardant et al. Biochim. Biophys. Acta. 1988 962 149

72. R.S. Chapkin et al. Biochem. Biophys. Res. Commun. 1988 153 799

73. C.C. Miler et al. Prostaglandins 1988 35 917

HEPOXILINS

HE-008
Hepoxilin A₃ (8,11(12)-HEpETrE)
8(R,S)-Hydroxy-11(S),12(S)-epoxyeicosa-5Z,9E,14Z-trienoic acid
50 µg/ml ethanol, 98%, MW=336.5, [85589-24-8] Structure - Scheme 3, Storage: -80°C. The two diastereomers may be separated by silica gel chromatography providing 8(R) (more polar) and 8(S) (less polar) hepoxilins¹. Biosynthesis via hemeprotein mediated rearrangement of 12-HPETE². Potentiates glucose dependent insulin secretion³. Opens S-type potassium channels in Aplysia^4,5. Modulates synaptic neurotransmission in rat hippocampus⁶. Raises intracellular calcium levels in human neutrophils⁷. Induces vascular permeability in rat skin⁸. Converted to a novel glutathione conjugate by glutathione transferase^1,9 and to isomeric triols by an epoxide hydrolase¹⁰.
50 µg
5 x 50 µg
1.0 mg

HE-010
Hepoxilin B₃ (10,11(12)-HEpETrE)
10(R,S)-Hydroxy-11(S),12(S)-trans-epoxyeicosa-5Z,8Z,14Z-trienoic acid
50 µg/ml ethanol, 98%, MW=336.5, Structure - Scheme 3, Storage: -80°C. Biosynthesis in pancreatic islets³, platelets¹¹ and rat lung¹².
50 µg
5 x 50 µg
1.0 mg

REFERENCES

1. C.R. Pace-Asciak et al. Proc. Natl. Acad. Sci. USA 1990 87 3037

2. C.R. Pace-Asciak J. Biol. Chem. 1984 259 8332

3. C.R. Pace-Asciak and J.M. Martin Prostagland. Leukotrienes

Med. l984 16 173

4. F. Belardetti et al. Neuron 1989 3 497

5. D. Piomelli et al. Proc. Natl. Acad. Sci. USA 1989 86 1721

6. C.R. Pace-Asciak et al. Biochem. Biophys. Res. Commun. 1990 173 949

7. S. Dho et al. Biochem. J. 1990 266 63

8. O. Laneuville et al. Eicosanoids 1991 4 95

9. O. Laneuville et al. J. Biol. Chem. 1990 265 21415

10. C.R. Pace-Asciak and W.-S. Lee J. Biol. Chem. 1989 264 9310

11. I.C. Walker et al. Prostaglandins 1979 18 173

12. C.R. Pace-Asciak J. Biol. Chem. 1983 258 6835

DiHETES

DS-056
5(S),6(R)-DiHETE
5(S),6(R)-Dihydroxyeicosa-7E,9E,11Z,14Z-tetraenoic acid
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 272 nm (40,000)¹ [82948-88-7] Structure - Scheme 1, Storage: -80°C. Biosynthesis via enzymatic^1,2 and nonenzymatic³ hydrolysis of LTA₄. Induces contraction of guinea pig lung parenchymal strips⁴. Partial agonist at LTD₄ receptors⁵. Potent inhibitor of LTB₄ induced neutrophil migration (IC₅₀=8 nM)⁶.
50 µg
5 x 50 µg
1.0 mg

D-512
5(S),12(S)-DiHETE
5(S),12(S)-Dihydroxyeicosa-6E,8Z,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 268 nm (40,000)⁷ [83709-73-3] Structure - Scheme 3, Storage: -80°C. Biosynthesis via transcellular metabolism (two successive lipoxygenase reactions)⁸. For a review of transcellular eicosanoid synthesis see reference 9. Partial agonist at LTB₄ receptors^10,11. Antagonizes LTB₄-induced human leukocyte aggregation by inducing homologous desensitization of LTB₄ receptors^10,11. Inhibits NK cell activity¹².
50 µg
5 x 50 µg
1.0 mg

DTS-512
5(S),12(S)-DiHETE (6-trans-12-epi-LTB₄)
5(S),12(S)-Dihydroxyeicosa-6E,8E,10E,14Z-tetraenoic acid
50 µg/ml ethanol, 99%, MW=336.5, UVmax: 268 nm (50,000) [73151-67-4] Structure - Scheme 1, Storage: -80°C. Biosynthesis via nonenzymatic hydrolysis of LTA₄¹³ and by myeloperoxidase dependent metabolism of cysteinyl leukotrienes¹⁴.
50 µg
5 x 50 µg
1.0 mg

DTR-512
5(S),12(R)-DiHETE (6-trans-LTB₄)
5(S),12(R)-Dihydroxyeicosa-6E,8E,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 268 nm (50,000) [71652-82-9] Structure - Scheme l, Storage: -80°C. Biosynthesis via nonenzymatic¹³ and enzymatic¹⁵ hydrolysis of LTA₄ and by myeloperoxidase dependent metabolism of cysteinyl leukotrienes¹⁴. Neutrophil chemotaxin in the guinea pig dermis¹⁶.
50 µg
5 x 50 µg
1.0 mg

D-515
5(S),15(S)-DiHETE
5(S),15(S)-Dihydroxyeicosa-6E,8Z,11Z,13E-tetraenoic acid
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 243 nm (33,500)¹⁷ [82200-87-1] Structure - Scheme 4, Storage: -80°C. Biosynthesis in human eosinophils¹⁸. Enhances neutrophil degranulation. Potent chemotaxin for human eosinophils²⁰.
50 µg
5 x 50 µg
1.0 mg

D-815
8(S),15(S)-DiHETE
8(S),15(S)-Dihydroxyeicosa-5Z,9E,11Z,13E-tetraenoic acid
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 268.5 nm (40,000)¹ [80234-65-7] Structure - Scheme 4, Storage: -80°C. Biosynthesis in eosinophils¹⁸, leukocytes²¹ and platelets²². Potent chemotaxin for human eosinophils²⁰.
50 µg
5 x 50 µg
1.0 mg

DTR-815
8(R),15(S)-DiHETE
8(R),15(S)-Dihydroxyeicosa-5Z,9E,11E,13E-tetraenoic acid
50 µg/ml ethanol, 99%, MW=336.5, UVmax: 268 nm (50,000) [80234-67-9] Structure - Scheme 4, Storage: -80°C. Produces a dose dependent hyperalgesia²³. Stereospecifically sensitizes C-fiber mechanoheat nociceptors²⁴.
50 µg
5 x 50 µg

DTS-815
8(S),15(S)-DiHETE
8(S),15(S)-Dihydroxyeicosa-5Z,9E,11E,13E-tetraenoic acid
50 µg/ml ethanol, 99%, MW=336.5, UVmax: 268 nm (50,000) [80234-66-8] Structure - Scheme 4, Storage: -80°C. Antagonizes hyperalgesic effects produced by 8(R),15(S)-DiHETE^23,24
50 µg
5 x 50 µg

D-122
12(S),20-DiHETE
12(S),20-Dihydroxyeicosa-5Z,8Z,10E,14Z-tetraenoic acid
50 µg/ml ethanol, >99%, MW=336.5, UVmax: 237 nm (23,000) [89614-44-8] Structure - Scheme 3, Storage: -20°C. Transcellular biosynthesis via interaction between platelets and neutrophils^25,26,27. For a review of transcellular eicosanoid synthesis see reference 9.
50 µg
5 x 50 µg

REFERENCES

1. J. Haeggström et al. J. Biol. Chem. 1986 261 6332

2. J. Haeggström et al. Biochim. Biophys. Acta 1988 958 469

3. P. Borgeat et al. J. Biol. Chem. 1979 254 7865

4. P. Sirois et al. Prostaglandins 1982 24 405

5. A. Muller et al. Prostaglandins 1989 38 635

6. T.H. Lee et al. Biochem. Biophys. Res. Commun. 1991 180 1416

7. P. Borgeat et al. Prostaglandins Med. 1981 6 557

8. J.A. Lindgren et al. FEBS Lett. 1981 128 329

9. J. Maclouf et al. Pharmacol. Res. 1989 21 1

10. H.E. Claesson et al. Biochim. Biophys. Acta 1984 804 52

11. D. Kiel et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1990 21A 403

12. W.E. Field II et al. Prostaglandins 1988 36 411

13. P. Borgeat et al. J. Biol. Chem. 1979 254 7865

14. C.W. Lee et al. J. Biol. Chem. 1983 258 15004

15. O. Breuer and S. Hammarström Biochem. Biophys. Res. Commun. 1987 142 667

16. D.J. Fretland J. Leukocyte Biol. 1991 49 283

17. C.P.A. Van Os et al. Biochim. Biophys. Acta 1981 663 177

18. J. Turk et al. J. Biol. Chem. 1982 257 7068

19. J.T. O'Flaherty et al. Prostaglandins Leukotrienes Med. 1985 17 199

20. E. Morita et al. J. Immunol. 1990 144 1893

21. S. Shak et al. J. Biol. Chem. 1983 258 14948

22. P. Wong et al. J. Biol. Chem. 1985 260 9162

23. J.D. Levine et al. Proc. Natl. Acad. Sci. USA 1986 83 5331

24. D.M. White et al. J. Neurophysiol. 1990 63 966

25. A.J. Marcus et al. Proc. Natl. Acad. Sci. USA 1984 81 903

26. P.Y.-K. Wong et al. J. Biol. Chem. 1984 259 2683

27. A.J. Marcus et al. J. Clin. Invest. 1987 79 179

LIPOXINS

LXA-004
Lipoxin A₄
5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acid
25 µg/ml ethanol, >99%, MW=352.5, UVmax: 300 nm (50,000)¹ [89663-86-5] Structure - Scheme 4, Storage: -80°C. Biosynthesis in human leukocytes^1,2 and rat alveolar macrophages³. Transcellular biosynthesis via interaction of human neutrophils⁴ or granulocytes⁵ and platelets. Produced in human nasal polyps and bronchial tissue⁶. Stimulates vasodilation^7,8 and antagonizes LTD₄ induced vasoconstriction⁸. Induces glomerular hyperperfusion and hyperfiltration⁹. Inhibits LTB₄ or FMLP induced leukocyte chemotaxis¹⁰ and blocks the mobilization of Ca²⁺ and IP₃¹¹. Inhibits LTB₄ induced inflammation in the hamster cheek pouch¹². Activates protein kinase C¹³. Regulates human myelopoiesis¹⁴. SAR¹⁰.
25 µg
5 x 25 µg

LXB-004
Lipoxin B₄
5(S),14(R),15(S)-Trihydroxyeicosa-6E,8Z,10E,12E-tetraenoic acid
25 µg/ml ethanol, >99%, MW=352.5, UVmax: 300 nm (50,000)¹⁵ [98049-69-5] Structure - Scheme 4, Storage: -80°C. Transcellular biosynthesis via interaction of human neutrophils⁴ or granulocytes⁵ and platelets. Stimulates vasodilation⁷. Constricts pulmonary parenchymal strips⁷. Regulates human myelopoiesis¹⁴.
25 µg
5 x 25 µg

REFERENCES

1. C.N. Serhan et al. J. Biol. Chem. 1986 261 16340

2. N. Ueda et al. Biochem. Biophys. Res. Commun. 1987 149 1063

3. S.J. Kim et al. Biochem. Biophys. Res. Commun. 1988 150 870

4. S. Fiore and C.N. Serhan J. Exp. Med. 1990 172 1451

5. C. Edenius et al. Biochem. Biophys. Res. Commun. 1988 157 801

6. C. Edenius et al. FEBS Lett. 1990 272 25

7. A.M. Lefer et al. Proc. Natl. Acad. Sci. USA 1988 85 8340

8. K.F. Badr et al. Proc. Natl. Acad. Sci. USA 1989 86 3438

9. K.F. Badr et al. Biochem. Biophys. Res. Commun. 1987 145 408

10. T. H. Lee et al. Biochem. Biophys. Res. Commun. 1991 180 1416

11. B.M. Grandordy et al. Biochem. Biophys. Res. Commun. 1990 167 1022

12. P. Hedqvist et al. Acta Physiol. Scand. 1989 137 571

13. A. Hansson et al. Biochem. Biophys. Res. Commun. 1986 134 1215

14. L. Stenke et al. Biochem. Biophys. Res. Commun. 1991 180 255

15. C.N. Serhan et al. Proc. Natl. Acad. Sci. USA 1986 83 1983

CYTOCHROME P-450 DERIVED EPOXIDES AND DIOLS

EE-56
(?5,6-EET (5(6)-EpETrE)
(?5,6-Epoxyeicosa-8Z,11Z,14Z-trienoic acid
50 µg/ml ethanol, 98%, MW=320.5, Structure - Scheme 5, Storage: -80°C. Mobilizes Ca²⁺ in anterior pituitary cells¹. Stimulates insulin release from rat pancreatic islets². Potent stimulator of prolactin secretion³. Potent vasodilator in the intestinal⁴ and cerebral⁵ microcirculation and in bovine coronary arteries⁶. Mediates angiotensin induced natriuresis⁷. Metabolized by cyclooxygenase^8,9. Review¹⁰. Assays: GCMS^11,12, stereochemical analysis by chiral phase HPLC¹³.
50 µg
5 x 50 µg
1.0 mg

EM-56
(?5,6-EET methyl ester (5(6)-EpETrE)
(?5,6-Epoxyeicosa-8Z,11Z,14Z-trienoic acid methyl ester
50 µg/ml ethanol, 98%, MW=334.5, Storage: -80°C
50 µg
5 x 50 µg
1.0 mg

EE-89
(?8,9-EET (8(9)-EpETrE)
(?8,9-Epoxyeicosa-5Z,11Z,14Z-trienoic acid
50 µg/ml ethanol, 98%, MW=320.5, Structure - Scheme 5, Storage: -20°C. Biosynthesis via liver cytochrome P-450¹⁴. Induces glucagon release from pancreatic islets². Vasodilator in intestinal microcirculation⁴ and bovine coronary arteries⁶. Metabolized by cyclooxygenase¹⁵. Review¹⁰. Assays: GCMS^11,12, stereochemical analysis by chiral phase HPLC¹³.
50 µg
5 x 50 µg
1.0 mg

EE-11
(?11,12-EET (11(12)-EpETrE)
(?11,12-Epoxyeicosa-5Z,8Z,14Z-trienoic acid
50 µg/ml ethanol, 98%, MW=320.5, Structure - Scheme 5, Storage: -20°C. Biosynthesis via liver¹⁴ and renal¹⁶ cytochrome P-450. Induces glucagon release from pancreatic islets². Vasodilator in intestinal microcirculation⁴. Inhibits Na⁺K⁺-ATPase¹⁷. Urinary excretion in humans is increased during pregnancy induced hypertension¹⁸. Review¹⁰. Assays: GCMS^11,12, stereochemical analysis by chiral phase HPLC¹³.
50 µg
5 x 50 µg
1.0 mg

EE-14
(?14,15-EET (14(15)-EpETrE)
(?14,15-Epoxyeicosa-5Z,8Z,11Z-trienoic acid
50 µg/ml ethanol, 98%, MW=320.5, Structure - Scheme 5, Storage: -20°C. Stimulates glucagon release from rat pancreatic islets². Urinary excretion in humans is increased during pregnancy induced hypertension¹⁸. Inhibits cyclooxygenase and platelet aggregation¹⁹. Inhibits vasopressin response²⁰. Induces monocyte adhesion to endothelial cells²¹. Inhibits renin release²². Decreases blood pressure in rats²³. Review¹⁰. Assays: GCMS^11,12 stereochemical analysis by chiral phase HPLC¹³.
50 µg
5 x 50 µg
1.0 mg

REFERENCES

1. G. Snyder et al. Biochem. Biophys. Res. Commun. 1986 139 1188

2. J.R. Falck et al. Biochem. Biophys. Res. Commun. 1983 114 743

3. R. Cashman et al. Neuroendocrinology 1987 76 246

4. K.G. Proctor et al. Circulation Res. 1987 60 50

5. E.F. Ellis et al. Am. J. Physiol. 1990 259 H1171

6. M. Rosolowsky et al. Adv. Prostagland. Thromboxane Leukotriene

Res. 1990 21 213

7. M. Romero et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1990 21 205

8. M. Balazy J. Biol. Chem. 1991 266 23561

9. E. Oliw and G.Benthin Biochem. Biophys. Res. Commun. 1985 126 1090

10. F.A. Fitzpatrick and R.C. Murphy Pharmacol. Rev. 1989 40 229

11. G.A. Ulsaker and G. Teien Analyst 1990 115 259

12. J. Turk et al. Methods Enzymol. 1990 187 175

13. T.D. Hammonds et al. Anal. Biochem. 1989 182 300

14. N. Chacos et al. Biochem. Biophys. Res. Commun. 1982 104 916

15. T. Homma et al. Biochem. Biophys. Res. Commun. 1993 191 282

16. D. Sacerdoti et al. Biochem. Pharmacol. 1988 37 521

17. M. Schwartzman et al. Nature 1985 317 620

18. F. Catella et al. Proc. Natl. Acad. Sci. USA 1990 87 5893

19. F.A. Fitzpatrick et al. J. Biol. Chem. 1986 261 15334

20. D. Schlondorff et al. Am. J. Physiol. 1987 253 F464

21. K.A. Pritchard et al. Biochem. Biophys. Res. Commun. 1990 167 137

22. W.L. Henrich et al. Amer J. Physiol. 1990 258 E269

23. W.-K. Lin et al. Biochem. Biophys. Res. Commun. 1990 167 977

OXO-METABOLITES

HA-004
(?4-Hydroxynon-2-enal
>97%, MW=156.2, UVmax: 219 nm (11,600), Storage: -20°C. Cytotoxic product of microsomal lipid peroxidation induced by xenobiotics¹. Reported to be a specific chemical indicator of lipid peroxidation in rat liver microsomes² and in myocardial reperfusion injury³. Covalently reacts with LDL⁴ and HDL⁵ during oxidative modification. Modifies proteins by covalent reaction with histidine and lysine residues⁶.
1 mg
10 mg

K-005
5-KETE (5-oxo-ETE)
5-Ketoeicosa-6E,8Z,11Z,13Z-tetraenoic acid
50 µg/ml ethanol, >98%, MW=318.5, UVmax: 279 nm, Storage: -80°C. Biosynthesis in human neutrophils⁷. Stimulates neutrophil degranulation and Ca²⁺ mobilization by a mechanism independent of the LTB₄ receptor^8,9.
50 µg
5 x 50 µg
1.0 mg

K-015
15-KETE (15-oxo-ETE)
15-Ketoeicosa-6Z,8Z,11Z,13E-tetraenoic acid
50 µg/ml ethanol, >98%, MW=318.5, UVmax: 279 nm, [81416-72-0] Structure - Scheme 4, Storage: -80°C. Biosynthesis via 15-OH prostaglandin dehydrogenase¹⁰ from lung¹¹ and liver microsomes¹² and by a nonenzymatic process¹³.
50 µg
5 x 50 µg
1.0 mg

REFERENCES

1. H. Esterbauer et al. Free Radic. Biol. Med. 1991 11 81

2. F.J.G.M. van Kuijk et al. Biochem. Biophys. Res. Commun. 1986 139 144

3. I.E Blasig et al. Am. J. Physiol. 1995 269 H14

4. G. Jürgens et al. Biochim. Biophys. Acta. 1986 875 103

5. M.R. McCall et al. Arterioscler. Thromb. Vasc. Biol. 1995 15 1599

6. D.V. Nadkarni and L.M. Sayre Chem. Res. Toxicol. 1995 8 284

7. W.S. Powell et al. J. Biol. Chem. 1992 267 19233

8. J.T. O'Flaherty et al. Biochim. Biophys. Acta 1994 1201 505

9. W.S. Powell et al. J. Immunol. 1996 156 336

10. A.P. Agins et al. Agents Actions 1987 21 397

11. J.M. Bergholte et al. Arch. Biochem. Biophys. 1987 257 444

12. D.-E. Sok et al. Biochem. Biophys. Res. Commun. 1988 156 524

13. S. Narumiya et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1982 9 77

EICOSANOID HPLC STANDARD MIXTURES

SM-100
HETE Mixture
Each ampule contains 10 µg of each of the following HETEs:
(?5-HETE, 12(S)-HETE and 15(S)-HETE dissolved in 600 µl ethanol.
1 ampule

SM-105
Cysteinyl Leukotriene Mixture
Each ampule contains 10 µg of each of the following leukotrienes: leukotriene C₄, leukotriene D₄ and leukotriene E₄ dissolved in 600 µl methanol/ammonium acetate buffer, 70:30, pH = 5.6.
1 ampule

SM-110
Leukotriene A₄ Hydrolysis Products (DiHETEs) Mixture
Each ampule contains 10 µg of each of the following LTA₄ hydrolysis products: leukotriene B₄, 5(S),6(R)-DiHETE, 6-trans-leukotriene B₄ and 12-epi-6-trans-leukotriene B₄ dissolved in 800 µl ethanol.
1 ampule

SM-115
Leukotriene B₄ and Omega Oxidation Metabolites Mixture
Each ampule contains 10 µg of each of the following: leukotriene B₄, 20-hydroxy leukotriene B₄ and 20-carboxy leukotriene B₄ dissolved in 600 µl ethanol.
1 ampule

PROSTAGLANDINS

PG-001
PGA₁
Prostaglandin A₁
99%, MW=336.5, [14152-28-4] Storage: -20°C. Biosynthesis from dihomo-g-linolenic acid¹. Stimulates renin release¹. Antitumor activity². Inhibits NFkB activation in several human cell lines³.
1 mg
10 mg

PG-002
PGA₂
Prostaglandin A₂
99%, MW=334.5, [13345-50-1] Structure - Scheme 6, Storage: -20°C. Identification in human seminal plasma⁴. Antitumor activity^2,5. Induces g-glutamylcysteine synthetase⁶ and apoptosis in L-1210 cells⁷.
1 mg
10 mg

PG-003
PGB₁
Prostaglandin B₁
99%, MW=336.5, [13345-51-2] Storage: -20°C. Biosynthesis from dihomo-g-linolenic acid.
1 mg
10 mg

PG-004
PGB₂
Prostaglandin B₂
99%, MW=334.5, UVmax: 278 nm (28,680)⁸, [13367-85-6] Structure - Scheme 6, Storage: -20°C. Most abundant prostaglandin released from osteoblasts⁹. Inhibits glucagon-stimulated hepatocyte cAMP accumulation¹⁰.
1 mg
10 mg

PG-005
PGD₂
Prostaglandin D₂
99%, MW=352.5, [41598-07-6] Structure - Scheme 6, Storage: -20°C. Principal cyclooxygenase product of the mast cell¹¹ and of the CNS¹². Inhibits platelet aggregation¹³ and activation of human neutrophils¹⁴. Potent vasodilator¹⁵. Constricts airway smooth muscle¹⁵. Induces sleep in monkeys¹⁶. Inhibits tumor cell proliferation¹⁷. Metabolized to 11b-PGF_2a¹⁸ and PGJ₂¹⁹ and by b-oxidation²⁰. Effects induced by receptor mediated elevation of cAMP²¹. Assays: TLC²², EIA,²³ Reviews^15,24.
1 mg
10 mg

PG-048
PGE₀
See 13,14-Dihydro-prostaglandin E₁

PG-006
PGE₁
Prostaglandin E₁
99%, MW=354.5, [745-65-3] Storage: -20°C. Biosynthesis from dihomo-g-linolenic acid²⁵. A major prostaglandin in semen^26,27. Inhibits human platelet aggregation²⁸. Effects induced by receptor mediated elevation of cAMP²⁹. Assays: HPLC (separation and quantification of PGE₁ and PGE₂)³⁰. Review³¹.
1 mg
10 mg

PG-007
PGE₂
Prostaglandin E₂
99%, MW=352.5, [363-24-6] Structure - Scheme 6, Storage: -20°C. Biosynthesis in numerous cell types. Potent vasodilator³². Exerts both anti- and proinflammatory activities by inhibition of mediator release and enhancement of mediator action^33,34. Stimulates bone resorption³⁵. Synergizes with LTB₄³⁶. Facilitates replication of AIDS virus³⁷. Regulates sleep/wake cycle³⁸. Thermoregulatory action in the CNS³⁹. Induces LHRH release from rat median eminence⁴⁰. Regulates renal hemodynamics and sodium excretion⁴¹. Protective effect on gastric mucosa⁴². Effects induced by receptor mediated elevation of cAMP⁴³. Assays: TLC²², RIA⁴⁴
1mg
10 mg

PG-010
PGF_1a
Prostaglandin F_1a
99%, MW=356.5, [745-62-0] Storage: -20°C. Biosynthesis from dihomo-g-linolenic acid.
1 mg
10 mg

PG-008
PGF_2a
Prostaglandin F_2a
99%, MW=354.5, [38562-01-5] Structure - Scheme 6, Storage: -20°C. A major uterine luteolytic prostaglandin⁴⁵. Assays: TLC²², EIA⁴⁶.
1 mg
10 mg

PG-009
PGF_2a·THAM
Prostaglandin F_2a·tromethamine
99%, MW=475.6, [38562-01-5] Storage: -20°C
1 mg
10 mg

PG-049
8-epi-PGF_2a
8-epi-Prostaglandin F_2a
1 mg/ml ethanol, 99%, MW=354.5, [27415-26-5] Storage: -20°C. Biosynthesis in humans by a non-cyclooxygenase, free radical-catalyzed mechanism⁴⁷. Also biosynthesized as a minor product from PGHS-1⁴⁸ and PGHS-2⁴⁹. Potent vasoconstrictor^50,51. Partial agonist at thromboxane receptors. A novel marker of endogenous lipid peroxidation⁵³.
1 mg
5 x 1 mg

PG-030
9b,11a-PGF₂
9b,11a-Prostaglandin F₂
99%, MW=354.5, [4510-16-1] Structure - Scheme 6, Storage: -20°C. Negative chronotropic activity⁵⁴. Bronchodilator, antagonizes effects of PGF₂⁵⁵.
1 mg
10 mg

PG-031
9a,11b-PGF₂
9a,11b-Prostaglandin F₂
99%, MW=354.5, [38432-87-0] Structure - Scheme 6, Storage: -20°C. Biosynthesis from PGD₂ via 11-keto reductase^56,57. Displays antiaggregatory⁵⁸, vasoconstrictor⁵⁸ and bronchoconstrictor⁵⁹ properties. Regulates water and electrolyte excretion⁶⁰. Assays: RIA⁶¹ GCMS⁶².
1 mg
10 mg

PH-002
PGH₂
Prostaglandin H₂
50 µg/ml hexane/ethylacetate (10:1), 98%, MW=352.5, [42935-17-1] Structure - Scheme 6, Storage: -80°C. A labile, platelet activating, cyclic endoperoxide intermediate in the biosynthesis of prostaglandins⁶³. Half life under physiological conditions is 5 minutes.
50 µg
5 x 50 µg

PG-011
PGI₂·Na
Prostaglandin I₂·Na (Prostacyclin)
99%, MW=374.5, [61849-14-7] Structure - Scheme 7, Storage: -20°C. Biosynthesis in endothelial cells⁶⁴. Induces vasodilation⁶⁵, inhibits platelet aggregation by receptor mediated stimulation of adenylate cyclase⁶⁶. Cytoprotective⁶⁷. Fibrinolytic⁶⁸. Review⁶⁹, clinical applications⁷⁰. Half life under physiological conditions is 2 minutes⁶⁹.
1 mg
10 mg

PG-033
PGJ₂
Prostaglandin J₂
98%, MW=334.5, UVmax: 216 nm (9,900)⁷¹, [60203-57-8] Structure - Scheme 6, Storage: -80°C. Biosynthesis via nonenzymatic dehydration of PGD₂⁷². Inhibits platelet aggregation⁷³ and aortic smooth muscle cell proliferation⁷⁴. Potent antineoplastic⁷⁵ and antiviral⁷⁶ activity. Inhibits phosphoinositide turnover⁷⁷. Review⁵.
1 mg
10 mg

REFERENCES

1. J. Hahn et al. Prostaglandins 1980 20 15

2. S. Marini et al. Br. J. Cancer 1990 61 394

3. A. Rossi et al. Proc. Natl. Acad. Sci. USA 1997 94 746

4. M. Hamberg et al. J. Biol. Chem. 1966 241 257

5. M. Fukushima Eicosanoids 1990 3 189

6. K. Ohno et al. Biochem. Biophys. Res. Commun. 1990 168 551

7. I.K. Kim et al. FEBS Lett. 1993 321 209

8. W.R. Mathews et al. Anal. Biochem. 1981 118 96

9. J.H.M. Feyen et al. Prostaglandins 1984 28 769

10. E. P. Brass et al. Biochem. J. 1990 267 59

11. R.A. Lewis et al. J. Immunol. 1982 129 1627

12. T. Ogorochi et al. J. Neurochem. 1984 43 71

13. J. B. Smith et al. Thromb. Res. 1974 5 291

14. P. Ney and K. Schrör Eicosanoids 1991 4 21

15. H. Giles and P. Leff Prostaglandins 1988 35 277

16. H. Onoe et al. Proc. Natl. Acad. Sci. USA 1988 85 4082

17. T. Sakai and N. Yamaguchi Prostaglandins 1984 27 17

18. C. Robinson et al. Biochem. Pharmacol. 1989 38 3267

19. F.A. Fitzpatrick and M.A. Wynalda J. Biol. Chem. 1983 258 11713

20. T. Sago et al. Biochim. Biophys. Acta 1986 879 330

21. S.T. Holgate et al. J. Immunol. 1980 125 1367

22. J.A. Salmon and R.J. Flower Methods Enzymol. 1982 86 477

23. O. Hiroshima et al. Prostaglandins 1986 32 63

24. S. Ito et al. Prostagland. Leukotrienes Essent. Fatty Acids 1989 37 219

25. J. Mai et al. Prostaglandins 1980 20 187

26. L. Speroff et al. Amer. J. Obstet. Gynec. 1978 107 1111

27. D. Rubin and M. Laposata J. Biol. Chem. 1991 266 23618

28. J. Kloeze Biochim. Biophys. Acta. 1969 187 285

29. N.P. Kurstjens et al. Biochem. Biophys. Res. Commun. 1990 167 1162

30. K. A. Krakauer et al. Prostaglandins 1986 32 301

31. S.J. Kirtland Prostagland. Leukotrienes Essent. Fatty Acids 1988 32 165

32. P.D.I. Richardson et al. Br. J. Pharmacol. 1976 57 581

33. J. Raud et al. Proc. Natl. Acad. Sci. USA 1988 85 2315

34. J.W. Christman et al. Prostaglandins 1991 41 251

35. L.G. Raisz et al. Nature 1977 267 532

36. C.B. Archer et al. Prostaglandins 1987 33 799

37. S. Kuno et al. Proc. Natl. Acad. Sci. USA 1986 83 3487

38. O. Hayaishi J. Biol. Chem. 1988 263 14593

39. A.S. Milton Ann. NY Acad. Sci. 1989 559 392

40. K. Gerozissis et al. Prostaglandins 1991 41 345

41. C.R. Long et al. Prostaglandins 1990 40 591

42. T.A. Miller Am. J. Physiol. 1983 245 G601

43. D.L. Bareis et al. Proc. Natl. Acad. Sci. USA 1983 80 2514

44. I. Alam et al. Anal. Biochem. 1979 93 339

45. D.L. Vincent et al. Prostaglandins 1986 31 715

46. Y. Hayashi and S. Yamamoto Methods Enzymol. 1982 86 269

47. J.D. Morrow et al. Proc. Natl. Acad. Sci. USA 1990 87 9383

48. D. Pratico et al. J. Biol. Chem. 1995 270 9800

49. D. Pratico and G. FitzGerald J. Biol. Chem. 1996 271 8919

50. K. Takahashi et al. J. Clin. Invest. 1992 90 136

51. M. Banerjee et al. Am. J. Physiol. 1992 263 H660

52. Y. Kingsly et al. J. Pharm. Pharm. Exp. Therap. 1994 270 1192

53. L.J. Roberts and J..D. Morrow Ann. NY Acad. Sci. 1994 744 237

54. T.T. Martinez et al. Prostaglandins 1977 14 449

55. M.E. Rosenthale et al. Prostaglandins 1973 3 767

56. T.E. Liston and L.J. Roberts II Proc. Natl. Acad. Sci. USA 1985 82 6030

57. Y. Urade et al. J. Biol. Chem. 1990 265 12029

58. G.Pugliese et al. J. Biol. Chem. 1985 260 14621

59. C.R.W. Beasley et al. J. Clin. Invest. 1987 79 978

60. C.T. Stier et al. J. Pharmacol. Exp. Ther. 1987 243 487

61. H. Hayashi et al. Prostaglandins 1987 33 517

62. D.F. Wendelborn et al. Methods Enzymol. 1990 187 51

63. M. Hamberg et al. Proc. Natl. Acad. Sci. USA 1974 71 345

64. B.B. Weksler et al. Proc. Natl. Acad. Sci. USA 1977 74 3922

65. S. Moncada et al. Pharmacol. Rev. 1979 30 293

66. J.E. Tateson et al. Prostaglandins 1977 13 389

67. J.R. Vane Adv. Prostagland. Thromboxane Leukotriene Res. 1983 11 449

68. A. Szczeklik et al. Thromb. Res. 1983 29 655

69. J.R. Vane Adv. Prostagland. Thromboxane Leukotriene Res. 1985 15 11

70. S. Moncada et al. Stroke 1983 14 157

71. G.L. Bundy et al. J. Med. Chem. 1983 26 790

72. M. Fukushima et al. Biochem. Biophys. Res. Commun. 1982 109 626

73. I. Mahmud et al. Prostagland. Leukotrienes Med. 1984 16 131

74. D.L. Smith et al. Prostagland. Leukotrienes Med. 1984 16 1

75. M. Fukushima et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1989 19 415

76. M.G. Santoro et al. J. Gen. Viral. 1987 68 1153

77. N. Nakahata et al. Prostaglandins 1990 40 405

PROSTAGLANDIN METABOLITES

PG-048
13,14-Dihydro-prostaglandin E₁ (PGE₀)
98%, MW=356.5, [19313-28-1] Storage: -80°C.
Circulating metabolite of PGE₁ in man¹. Vasodilator equipotent with PGE₁². Inhibits human platelet aggregation^2,3. Antimitotic activity⁴.
1 mg
10 mg

PG-038
19(R)-Hydroxy-prostaglandin E₂
50 µg/100 µl ethanol, 98% MW=368.5, [64625-54-3] Structure - Scheme 6, Storage: -20°C. Occurrence in human seminal vesicles^5,6. Selective EP₂ receptor agonist⁷.
50 µg
5 x 50 µg
1 mg

PG-013
15-Keto-prostaglandin E₂
99%, MW=350.5, [26441-05-4] Structure - Scheme 6, Storage: -20°C.
Biosynthesis via 15-hydroxyprostaglandin dehydrogenase^8,9.
1 mg
10 mg

PG-034
2,3-Dinor-6-keto-prostaglandin F_1a
98%, MW=342.5, Structure - Scheme 7, Storage: -20°C
Major human urinary metabolite of prostacyclin¹⁰. Assays: EIA¹¹, GCMS¹²
100 µg
1 mg

PG-017
6-Keto-prostaglandin F_1a
99%, MW=370.5, [58962-34-8] Structure - Scheme 7, Storage: -20°C. Biosynthesis via hydrolysis of prostacyclin^13,14. A reliable parameter for measurement of prostacyclin. Assays: TLC¹⁵, EIA¹¹, RIA¹⁶, GCMS¹²
1 mg
10 mg

PG-016
13,14-Dihydro-15-keto-prostaglandin F_2a
99%, MW=354.5 [27376-76-7] Structure - Scheme 6, Storage: -20°C
Biosynthesis via 15-hydroxyprostaglandin dehydrogenase⁸. Major plasma metabolite of PGF_2a¹⁷. Assays: RIA¹⁸, EIA¹⁹
1 mg
10 mg

PG-039
19(R)-Hydroxy-prostaglandin F_2a
98%, 50 µg/ml ethanol, MW=370.5, [64625-53-2] Structure - Scheme 6, Storage: -20°C
Occurrence in human semen²⁰.
50 µg
5 x 50 µg

PG-015
15-Keto-prostaglandin F_2a
99%, [35850-13-6] MW=352.5, Structure - Scheme 6, Storage: -20°C
Biosynthesis via 15-hydroxyprostaglandin dehydrogenase^8,9.
1 mg
10 mg

PG-047
D¹²-PGJ₂
12-Prostaglandin J₂
98%, MW=334.5, UVmax: 244 nm (6,100)²¹, [87893-54-7] Structure - Scheme 6, Storage: -80°C.
Biosynthesis via albumin catalyzed isomerization of PGJ₂²². Potent antineoplastic and antiviral²³ activity. Induces apoptosis²⁴. Inhibits phosphoinositide turnover²⁵. Is converted to a novel glutathione conjugate²⁶. Assay: RIA²⁷. Review²⁸.
1 mg
10 mg

PG-050
15d-PGJ₂
15 DeoxyD^12,14-Prostaglandin J₂
97%, MW=316.5 [87893-55-8] Storage: -20°C
PPARg ligand. Promotes differentiation of fibroblasts to adipocytes^29,30.
1 mg

5 mg

HRT-012
12(S)-HHT (12-HHTrE)
12(S)-Hydroxyheptadeca-5Z,8E,10E-trienoic acid
50 µg/ml ethanol, >99%, MW=280.4, UVmax: 232 nm (33,400) [54397-84-1] Structure - Scheme 7, Storage: -80°C. Biosynthesis with TXA₂³¹ from PGH₂³². Inhibits human platelet aggregation³³. Stimulates prostacyclin production^35,36. Metabolized to 12-KHT via 15-hydroxyprostaglandin dehydrogenase²⁴ in human erythrocytes³³. A useful parameter for measuring cyclooxygenase activity³⁷. Assays: HPLC³⁷, GCMS³⁸, TLC¹⁵.
50 µg
5 x 50 µg
1 mg

REFERENCES

1. B.A. Peskar et al. Prostaglandins 1991 41 225

2. P. Ney et al. Eicosanoids 1991 4 177

3. J. Westwick Br. J. Pharmacol. 1976 58 297P

4. P. Fitscha et al. Eicosanoids 1991 4 231

5. E.H. Oliw et al. J. Biol. Chem. 1986 261 9216

6. P.L. Taylor et al. Nature 1974 250 665

7. D.F. Woodward et al. Prostaglandins 1993 46 371

8. H.S. Hansen Prostaglandins 1976 12 647

9. C. Moussard et al. Prostaglandins 1986 31 489

10. A.R. Brash et al. J. Pharmacol. Exp. Ther. 1983 226 78

11. F. Lellouche et al. Prostaglandins 1990 40 297

12. S. Fischer and C.O. Meese Biomed. Mass Spectrom. 1985 12 399

13. B. Rosenkranz et al. Biochim. Biophys. Acta 1980 619 207

14. C. Pace-Asciak J. Am. Chem. Soc. 1976 98 2348

15. J.A. Salmon and R.J. Flower Methods Enzymol. 1982 86 477

16. J. Maclouf Methods Enzymol. 1982 86 273

17. Y. Manabe et al. Prostaglandins 1987 33 757

18. E. Granström and H. Kindahl Methods Enzymol. 1982 86 320

19. K. Yokota et al. Biochim. Biophys. Acta 1986 879 322

20. P.L. Taylor et al. FEBS Lett. 1975 57 22

21. Y. Kikawa et al. Proc. Natl. Acad. Sci. USA 1984 81 1317

22. S. Narumiya and M. Fukushima J. Pharmacol. Exp. Ther. 1986 239 500

23. C. D'onofrio et al. Pharmacol. Res. 1989 21 665

24. I.K. Kim et al. FEBS Lett. 1993 321 209

25. N. Nakahata et al. Prostaglandins 1990 40 405

26. J. Atsmon et al. Cancer Res. 1990 50 1879

27. Y. Hirata et al. J. Biol. Chem. 1988 263 16619

28. M. Fukushima Eicosanoids 1990 3 189

29. B. M. Forman et al. Cell 1995 83 803

30. S.A. Kliewer et al. Cell 1995 83 813

31. M. Hecker et al. Arch. Biochem. Biophys. 1987 254 124

32. U. Diczfalusy et al. FEBS Lett. 1977 84 271

33. M. Hecker and V. Ullrich Eicosanoids 1988 1 19

34. P.D. Sadowitz et al. Prostaglandins 1987 34 749

35. A.P. Agins et al. Biochem. Pharmacol. 1987 36 1799

36. Y. Liu et al. Biochem. Biophys. Res. Commun. 1985 129 268

37. F.J. Sweeney et al. Prostagland. Leukotrienes Med. 1987 26 171

38. U. Hufmann et al. Anal. Biochem. 1990 189 244

THROMBOXANE AND METABOLITES

Thromboxane A₂ is a labile platelet aggregating and vasoconstricting substance with a half life of 37 seconds under physiological conditions. Structure - Scheme 7, Reviews^1,2,3

TB-002
TXB₂
Thromboxane B₂
99%, MW=370.5, [54397-85-2] Structure - Scheme 7, Storage: -20°C. Biosynthesis from thromboxane A₂ (reviews^1,2,3) via nonenzymatic hydration^4,5. Assays: TLC⁶, RIA⁷, EIA⁸, GCMS⁹.
1 mg
10 mg

TB-005
2,3-Dinor-TXB₂
2,3-Dinor-thromboxane B₂
98%, MW=342.4 [63250-09-9] Structure - Scheme 7, Storage: -20°C. Major human urinary thromboxane metabolite⁵. Assays: EIA¹⁰, GCMS^11,12.
50 µg
5 x 50 µg

TB-004
11-Dehydro-TXB₂
11-Dehydro-thromboxane B₂
99%, MW=368.5 [67910-12-7] Structure - Scheme 7, Storage: -20°C. A major, long lived metabolite of TXB₂ in human plasma^4,13. A reliable parameter for the measurement of thromboxane production in vivo^14,15. Assays: TLC¹⁶, RIA¹⁷, EIA¹⁰, GCMS^12,18.
1 mg
10 mg

REFERENCES

1. S. Moncada et al. Pharmacol. Rev. 1978 30 293

2. H. Sinzinger et al. Eicosanoids 1990 3 59

3. E.F. Smith III Eicosanoids 1989 2 199

4. L.J. Roberts et al. J. Biol. Chem. 1981 256 8384

5. L.J. Roberts et al. J. Biol. Chem. 1977 252 7415

6. J.A. Salmon and R.J. Flower Methods Enzymol. 1982 86 477

7. F. Fitzpatrick Methods Enzymol. 1982 86 286

8. M. Reinke et al. Prostaglandins 1989 37 577

9. C.O. Meese et al. Biomed. Mass Spectrom. 1985 12 554

10. F. Lellouche et al. Prostaglandins 1990 40 297

11. J.A. Lawson et al. Anal. Biochem. 1985 150 463

12. F. Catella and G. FitzGerald Methods Enzymol. 1990 187 42

13. F. Catella et al. Proc. Natl. Acad. Sci. USA 1986 83 5861

14. M. Kumlin et al. Prostaglandins 1986 32 741

15. J.A. Lawson et al. Anal. Biochem. 1986 155 198

16. P. Westlund et al. Prostaglandins 1986 31 929

17. G. Ciabattoni et al. Methods Enzymol. 1990 187 34

18. R. Lorenz et al. Prostaglandins 1989 38 157