Δ7-Prostaglandin C1: A primary metabolite of antitumor Δ7-prostaglandin A1 in the sera

Tetrahedron

Volumn 53, Issue 50, 1997, Pages 17009-17014

  Suzuki, Masaaki ^a   Kiho, Toshihiro ^b   Furuta, Kyoji ^a   Fukushima, Shoji ^c   Takeuchi, Yoshikazu ^c   Noyori, Ryoji ^b  

^a GIFU UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

15 HYDROXY 9 OXOPROSTA 7,10,13 TRIENOIC ACID; DELTA7 PROSTAGLANDIN C1; DRUG METABOLITE; PROSTAGLANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG METABOLISM; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RAT; THIN LAYER CHROMATOGRAPHY;

ANIMALIA;

EID: 0030734727     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10151-X     Document Type: Article

References (23)

1. Suzuki, M.; Mori, M.; Niwa, T.; Hirata, R.; Furuta, K.; Ishikawa, T.; Noyori, R. J Am. Chem. Soc. 1997, 119, 2376, and references cited therein.
2. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189.
3. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1.
4. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131.
5. For recent progress on the mechanism of the biological action of 1 and 2, see: (d) Noyori, R.; Suzuki, M. Science 1993, 259, 44.
6. (e) Noyori, R.; Koyano, H.; Mori, M.; Hirata, R.; Shiga, Y.; Kokura, T.; Suzuki, M. Pure Appl. Chem. 1994, 66, 1999.
7. (f) Akimaru, K.; Kuo, M. T.; Furuta, K.; Suzuki, M.; Noyori, R.; Ishikawa, T. Cytotechnology 1996, 19, 221.
8. (g) Higashiyama, K.; Niiya, K.; Ozawa, T.; Hayakawa, Y.; Fujimaki, M.; Sakuragawa, N. Prostaglandins 1996, 52, 143.
9. (h) Kim, H-S.; Lee, J-H.; Kim, I-K. Prostaglandins 1996, 57, 413.
10. (i) Akimaru, K.; Nakanishi, M.; Suzuki, M.; Furuta, K.; Noyori, R.; Ishikawa, T. In Eicosanoids and Other Bioactive Lipids in Cancer, Inflammation, and Radiation Injury; Honn, K. V., Nigam, S., Jones, R., Marnette, L. J., Wong, P. Y-K., Eds.; Plenum Press: New York, in press.
11. (a) Sugiura, S.; Toru, T.; Tanaka, T.; Hazato, A.; Okamura, N.; Bannai, K.; Manabe, K.; Kurozumi, S.; Noyori, R. Chem. Pharm. Bull. 1984, 32, 4658.
12. (b) Kato, T.; Fukushima, M.; Kurozumi, S.; Noyori, R. Cancer Res. 1986, 46, 3538.
13. (c) Suzuki, M.; Kawagishi, T.; Yanagisawa, A.; Suzuki, T.; Okamura, N.; Noyori, R. Bull. Chem. Soc. Jpn. 1988, 61, 1299.
14. (d) Suzuki, M.; Morita, Y.; Koyano, H.; Koga, M.; Noyori, R. Tetrahedron 1990, 46, 4809.
15. (e) Noyori, R.; Suzuki, M. Chemtracts-Org. Chem. 1990, 3, 173.
16. (a) Fukushima, M. In Eicosanoids and Other Bioactive Lipids in Cancer, Inflammation and Radiation Injury; Nigam, S., Marnett, L. J., Honn, K. V., Walden, T. L. Jr., Eds.; Kluwer Academic Publishers: Boston, 1993; pp 737-739.
17. (b) Kikuchi, Y.; Kita, T.; Hirata, J.; Fukushima, M. Cancer and Metastasis Rew. 1994, 13, 309.
18. (c) Fukushima, M.; Sasaki, H.; Fukushima, S. Annals of New York Acad. Sci. 1994, 744, 161.
19. (a) Polet, H.; Levine, L. J. Biol. Chem. 1975, 250, 351, and references cited therin.
20. For degradation of A-type PGs in human red cells, see: (b) Smith, J. B.; Silver, M. J.; Ingerman, C. M.; Kocsis, J. J. Prostaglandins, 1975, 9, 135.
21. 2, see: Corey, E. J.; Cyr, C. R. Tetrahedron Lett. 1974, 19, 1761.
22. The acid 7 was fairly labile and decomposed by concentration.
23. 6