OCTADECANOIDS - LINOLEIC ACID METABOLITES
HO-309
(?9-HODE
(?9-Hydroxyoctadeca-10E,12Z-dienoic acid
50 µg/ml ethanol, >99%, MW=296.5, UVmax: 234 nm (23,000), Storage: -20°C.
50 µg
5 x 50 µg
1.0 mg
HO-409
9(S)-HODE
9(S)-Hydroxyoctadeca-10E,12Z-dienoic acid
50 µg/ml ethanol, >99%, MW=296.5, UVmax: 234 nm (23,000) [73543-67-6] Structure -
Scheme 8, Storage: -20°C. Biosynthesis by endothelial cells1,
rabbit peritoneal serous membranes2, atherosclerotic plaques3 and healthy blood vessels4.
Biosynthesis via cyclooxygenase5 (9-OH stereochemistry was
not determined) or lipoxygenase6 pathways.
50 µg
5 x 50 µg
1.0 mg
HR-013
(?13-HODE
(?13-Hydroxyoctadeca-9Z,11E-dienoic acid
50 µg/ml ethanol, >99%, MW=296.5, UVmax: 234 nm (23,000) [73804-64-5] Storage: -20°C.
Occurence in psoriatic skin7.
50 µg
5 x 50 µg
1.0 mg
HO-013
13(S)-HODE
13(S)-Hydroxyoctadeca-9Z,11E-dienoic acid
50 µg/ml ethanol, >99%, MW=296.5, UVmax: 234 nm (23,000) [29623-28-7] Structure -
Scheme 8, Storage: -20°C. Biosynthesis in rabbit peritoneal serous membranes2,
atherosclerotic plaques3, healthy blood vessels4,
heart mitochondria8, psoriatic skin9,
VX2 carcinoma cells10, endothelial cells11, and macrophages12. Stimulates
prostacyclin production by endothelial cells13. Inhibits
thromboxane production in human platelets14. Inhibits
platelet11 and tumor cell15,16,17
adhesion to endothelium. Antagonizes 12-HETE induced tumor cell adhesion to endothelium17. Stimulates DNA synthesis in BALB/c 3T3 fibroblasts18.
50 µg
5 x 50 µg
1.0 mg
HP-019
9(S)-HPODE
9(S)-Hydroperoxyoctadeca-10E,12Z-dienoic acid
50 µg/ml ethanol, >99%, MW=312.5, UVmax: 234 nm (23,000) [29774-12-7] Structure -
Scheme 8, Storage: -20°C.
50 µg
5 x 50 µg
HP-013
13(S)-HPODE
13(S)-Hydroperoxyoctadeca-9Z,11E-dienoic acid
50 µg/ml ethanol, 98%, MW=312.5, UVmax: 234 nm (23,000) [33964-75-9] Structure - Scheme
8, Storage:-80°C. Suppresses activation of platelets19.
Induces endothelial injury20. Constricts isolated coronary
arteries21. Inhibits prostacyclin synthase22.
50 µg
5 x 50 µg
1.0 mg
KO-013
13-KODE
13-Keto-octadeca-9Z,11E-dienoic acid
50 µg/ml, 98%, MW=294.5, UVmax: 277 nm (22,000)23,
Structure - Scheme 8, Storage: -80°C. Biosynthesis from 13-HODE via dehydrogenases24,25. Occurs in membranes oxidized by reticulocyte LO26.
50 µg
5 x 50 µg
1.0 mg
LE-009
(?9,10-EODE (9(10)-EpOME, Leukotoxin)
(?9,10-Epoxyoctadec-12Z-enoic acid
50 µg/ml ethanol, 98%, MW=296.5, Structure - Scheme 8, Storage: -20°C. Biosynthesis in
leukocytes27, burned skin28,29
and lung lavages of patients with adult respiratory distress syndrome27.
Displays an uncoupling effect on mitochondrial respiration and potent relaxation of rat
stomach smooth muscle30. Effects in the cardiovascular
system include circulatory collapse31, cardiac failure32,33, vasoconstriction33 and
endothelial cell damage34.
50 µg
5 x 50 µg
LE-012
(?12,13-EODE (12(13)-EpOME)
(?12,13-Epoxyoctadec-9Z-enoic acid
50 µg/ml ethanol, 98%, MW=296.5, Structure - Scheme 8, Storage:-20°C. Biosynthesis in
leukocytes27,30. Cardiovascular effects33.
50 µg
5 x 50 µg
HO-313
13(S)-HOTE (13(S)-HOTrE)
13(S)-Hydroxyoctadeca-6Z,9Z,11E-trienoic acid
50 µg/ml ethanol, >99%, MW=294.5, UVmax: 236 nm (23,000) [74784-20-6] Storage: -20°C
50 µg
5 x 50 µg
1.0 mg
REFERENCES
1. T.L. Kaduce et al. J. Biol. Chem. 1989 264 6823
2. M. Claeys et al. Biochim. Biophys. Acta 1982 713 160
3. C.J.W. Brooks et al. Atherosclerosis 1971 13 223
4. C.D. Funk et al. J. Biol. Chem. 1985 260 7481
5. F. Engels et al. FEBS Lett. 1986 209 249
6. C.P.A. Van Os et al. Biochim. Biophys. Acta 1979 575 479
7. A.N. Baer et al. J. Lipid Res. 1990 31 125
8. G.A. Blondin Ann. NY Acad. Sci. 1975 264 98
9. R.D.R. Camp et al. Prostaglandins 1983 26 431
10. W.C. Hubbard et al. Prostaglandins 1980 20 431
11. M.R. Buchanan et al. J. Biol. Chem. 1985 260 16056
12. U.F. Schade et al. Biochem. Biophys. Res. Commun. 1987 147 695
13. B.N.Y. Setty et al. Biochem. Biophys. Res. Commun. 1987 146 502
14. 13. B.N.Y. Setty et al. Biochem. Biophys. Res. Commun. 1987 148 528
15. E. Bastida et al. J. Lipid Mediators 1990 2 281
16. T.A. Haas et al. Biochim. Biophys. Acta 1990 1051 174
17. I.M. Grossi et al. Cancer Res. 1989 49 1029
18. W.C. Glasgow and T.E. Eling Mol. Pharmacol. 1990 38 503
19. H. Bult et al. Adv. Prostagland. Thromboxane Leukotriene Res. 1987 17 224
20. M. Mizukami et. al. Arzneim Forsch. 1984 5 569
21. J.Z. Sun et. al. Med. Sci. Res. 1987 15 1449
22. J.A. Salmon et al. Biochim. Biophys. Acta 1978 523 250
23. E. Vioque et al. Arch. Biochem. Biophys. 1962 99 522
24. A.P. Agins et al. Agents Actions 1987 21 397
25. S.M. Earles et al. Biochim. Biophys. Acta 1991 1081 174
26. H. Kuhn et al. Arch. Biochem. Biophys. 1990 279 218
27. M. Hayakawa et al. Biochem. Biophys. Res. Commun. 1986 137 424
28. T. Ozawa et al. Biochem. Biophys. Res. Commun. 1988 152 1310
29. K. Suzuki et al. Burns 1981 8 110
30. T. Ozawa et al. Biochem. Biophys. Res. Commun. 1986 134 1071
31. A. Fukushima et al. Cardiovasc. Res. 1988 22 213
32. S. Sugiyama et al. Life Sciences 1986 40 225
33. M.R. Siegfried et al. Life Sciences 1990 46 427
34. T. Ozawa et al. Am. Rev. Resp. Dis. 1988 137 535
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