Chemical implications for antitumor and antiviral prostaglandins: Reaction of Δ7-prostaglandin A1 and prostaglandin A1 methyl esters with thiols

Journal of the American Chemical Society

Volumn 119, Issue 10, 1997, Pages 2376-2385

  Suzuki, Masaaki ^a   Mori, Makoto ^b   Niwa, Terutake ^a   Hirata, Ryu ^b   Furuta, Kyoji ^a   Ishikawa, Toshihisa ^c   Noyori, Ryoji ^b  

^a GIFU UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROSTAGLANDIN A1 METHYL ESTER; PROSTAGLANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CONJUGATION; CYTOTOXICITY; DRUG BINDING; DRUG TRANSPORT; GENE EXPRESSION REGULATION; IN VITRO STUDY; MODEL; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0030897596     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9628359     Document Type: Article

References (123)

1. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
2. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
3. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
4. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
5. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
6. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
7. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
8. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
9. For reviews, see: (a) Fukushima, M. Eicosanoids 1990, 3, 189. (b) Fukushima, M. Prostaglandins, Leukotrienes Essent. Fatty Acids 1992, 47, 1. (c) Sasaki, H.; Fukushima, M. Anti-Cancer Drugs 1994, 5, 131. For earlier important papers which opened this fascinating scientific area, see: (d) Prasad, K. N. Nature New Biol. 1972, 236, 49. (e) Santoro, M. G.; Phifpott, G. W.; Jaffe, B. Nature 1976, 263, 777. (f) Honn, K. V.; Cicone, B.; Skoff, A. Science 1981, 212, 1270. (g) Fukushima, M.; Kato, T.; Ueda, R.; Ota, K.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 105, 956. (h) Fukushima, M.; Kato, T.; Ota, K.; Arai, Y.; Narumiya, S.; Hayaishi, O. Biochem. Biophys. Res. Commun. 1982, 109, 626. (i) Fukushima, M.; Kato, T. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayaishi, O., Yamamoto, S., Eds.; Raven Press: New York, 1985; pp 415-418.
10. Prostaglandins in Cancer Research; Garaci, E., Paoletti, R., Santoro, M. G., Eds.; Springer-Verlag: Berlin, 1987; monograph.
11. (a) Bergman, M. D.; Sander, D.; Meyskens, F. L., Jr. Biochem. Biophys. Res. Commun. 1982, 704, 1080.
12. (b) Wiley, M. H.; Feingold, K. R.; Grunfeld, C.; Quesney-Huneeus, V.; Wu, J. M. J. Biol. Chem. 1983, 258, 491.
13. (c) Hughes-Fulford, M.; Wu, J.; Kato, T.; Fukushima, M. Adv. Prostaglandin, Thromboxane Leukotriene Res. 1985, 15, 401.
14. (d) Narumiya, S.; Fukushima, M. Biochem. Biophys. Res. Commun. 1985, 127, 739.
15. (e) Bhuyan, B. K.; Adams, E. G.; Badiner, G. J.; Li, L. H.; Barden, K. Cancer Res. 1986, 46, 1688.
16. (f) Ishioka, C.; Kanamaru, R.; Sato, T.; Dei, T.; Konishi, Y.; Asamura, M.; Wakui, A. Cancer Res. 1988, 48, 2813.
17. (g) Hughes-Fulford, M. J. Cell. Biochem. 1994, 54, 265.
18. (h) Sasaguri, T.; Masuda, J.; Shimokado, K.; Yokota, T.; Kosaka, C.; Fujishima, M.; Ogata, J. Exp. Cell Res. 1992, 200, 351.
19. (i) Kim, I.-K.; Lee, J.-H.; Sohn, H.-W.; Kim, H.-S.; Kim, S.-H. FEBS Lett. 1993, 321, 209.
20. For a review, see: (J) Narumiya, S.; Fukushima, M. In Eicisanoids and Other Bioactive Lipids in Cancer and Radiation Injury; Honn, K. V., Mamett, L. J., Nigam, S., Waiden, T., Jr., Eds.; Kluwer Academic Publishers: Boston, MA, 1989; pp 439-448.
21. For recent attention from cell differentiation and development including osteogenesis and adipogenesis, see: (k) Ohta, T.; Azuma, Y.; Kanatani, H.; Kiyoki, M.; Koshihara, Y. J. Pharmacol. Exp. Ther. 1995, 275, 450.
22. (l) Odani, N.; Negishi, M.; Takahashi, S.; Ichikawa, A. Biochem. Biophys. Res. Commun. 1996, 220, 264.
23. (m) Forman, B. M.; Tontonoz, P.; Chen, J.; Brun, R. P.; Spiegelman, B. M.; Evans, R. M. Cell 1995, 83, 803.
24. (n) Kliewer, S. A.; Lenhard, J. M.; Willson, T. M.; Patel, I.; Morris, D. C.; Lehmann, J. M. Cell 1995, 83, 813.
25. (a) Santoro, M. G.; Banedetto, A.; Garruba, G.; Garaci, E. Science 1980, 209, 1039.
26. (b) Santoro, M. G.; Fukushima, M.; Benedetto, A.; Amici, C. J. Gen. Virol. 1987, 68, 1153.
27. (c) Yamamoto, N.; Fukushima, M.; Tsurumi, T.; Maeno, K.; Nishiyama, Y. Biochem. Biophys. Res. Commun. 1987, 146, 1425.
28. (d) Yamamoto, N.; Rahman, M. M.; Fukushima, M.; Maeno, K.; Nishiyama, Y. Biochem. Biophys. Res. Commun. 1989, 158, 189.
29. (e) Fukushima, M.; Kato, T.; Narumiya, S.; Mizushima, Y.; Sasaki, H.; Terashima, Y.; Nishiyama, Y.; Santro, M. G. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1989; pp 415-418.
30. For a review, see: (f) Parker, J.; Ahrens, P. B.; Ankel, H. Antiviral Res. 1995, 26, 83.
31. (a) Kato, T.; Fukushima, M.; Kurozumi, S.; Noyori, R. Cancer Res. 1986, 46, 3538.
32. (b) Fukushima, M. In Role of Lipids in Cancer Research. III. The Pharmacological Effect of Lipids; Kabera, J. J., Ed.; American Oil Chemist Society: Chicago, IL, 1989; pp 215-221.
33. (c) Sasaki, H.; Mah, J.; Terashima, Y.; Fukushima, M. Proc. Am. Assoc. Cancer Res. 1989, 30, 582.
34. (d) Sasaki, H.; Takada, K.; Terashima, Y.; Ekimoto, H.; Takahashi, K.; Tsuruo, T.; Fukushima, M. Gynecol. Oncol. 1991, 41, 36. See also: refs 4b, c, and e.
35. (a) Suzuki, M.; Kawagishi, T.; Yanagisawa, A.; Suzuki, T.; Okamura, N.; Noyori, R. Bull. Chem. Soc. Jpn. 1988, 61, 1299.
36. (b) Suzuki, M.; Morita, Y.; Koyono, H.; Noyori, R. Tetrahedron 1990, 46, 4809.
37. For a review, see: (c) Noyori, R.; Suzuki, M. Chemtracts: Org. Chem. 1990, 3, 173.
38. (a) Fukushima, M. In Eicosanoids and Other Bioactive Lipids in Cancer, Inflammation and Radiation Injury; Nigam, S., Marnett, L. J., Honn, K. V., Waiden, T. L., Jr., Eds.; Kluwer Academic Publishers: Boston, MA, 1993; pp 737-739.
39. (b) Kikuchi, Y.; Kita, T.; Hirata, J.; Fukushima, M. Cancer Metastasis Rev. 1994, 13, 309.
40. (c) Fukushima, M.; Sasaki, H.; Fukushima, S. Ann. N.Y. Acad. Sci. 1994, 744, 161.
41. For a preliminary report, see: (a) Noyori, R. Suzuki, M. Science 1993, 259, 44. (b) Noyori, R.; Koyano, H.; Mori, M.; Hirata, R.; Shiga, Y.; Kokura, T.; Suzuki, M. Pure Appl. Chem. 1994, 66, 1999.
42. For a preliminary report, see: (a) Noyori, R. Suzuki, M. Science 1993, 259, 44. (b) Noyori, R.; Koyano, H.; Mori, M.; Hirata, R.; Shiga, Y.; Kokura, T.; Suzuki, M. Pure Appl. Chem. 1994, 66, 1999.
43. 7-PGA type compounds, see: (a) Kikuchi, H.; Tukitani, Y.; Iguchi, K.; Yamada, Y. Tetrahedron Lett. 1982, 23, 517. (b) Kobayashi, H.; Yasuzawa, T.; Yoshikawa, M.; Akatsu, H.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1982, 23, 5331. (c) Baker, B. J.; Okuda, R. K.; Yu, P. T.; Scheuer, P. J. J. Am. Chem. Soc. 1985, 107, 2976. See also: (d) Suzuki, M.; Morita, Y.; Yanagisawa, A.; Baker, B. J.; Scheuer, P. J.; Noyori, R. J. Org. Chem. 1988, 53, 286. For antiproliferative activity, see: ref li.
44. 7-PGA type compounds, see: (a) Kikuchi, H.; Tukitani, Y.; Iguchi, K.; Yamada, Y. Tetrahedron Lett. 1982, 23, 517. (b) Kobayashi, H.; Yasuzawa, T.; Yoshikawa, M.; Akatsu, H.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1982, 23, 5331. (c) Baker, B. J.; Okuda, R. K.; Yu, P. T.; Scheuer, P. J. J. Am. Chem. Soc. 1985, 107, 2976. See also: (d) Suzuki, M.; Morita, Y.; Yanagisawa, A.; Baker, B. J.; Scheuer, P. J.; Noyori, R. J. Org. Chem. 1988, 53, 286. For antiproliferative activity, see: ref li.
45. 7-PGA type compounds, see: (a) Kikuchi, H.; Tukitani, Y.; Iguchi, K.; Yamada, Y. Tetrahedron Lett. 1982, 23, 517. (b) Kobayashi, H.; Yasuzawa, T.; Yoshikawa, M.; Akatsu, H.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1982, 23, 5331. (c) Baker, B. J.; Okuda, R. K.; Yu, P. T.; Scheuer, P. J. J. Am. Chem. Soc. 1985, 107, 2976. See also: (d) Suzuki, M.; Morita, Y.; Yanagisawa, A.; Baker, B. J.; Scheuer, P. J.; Noyori, R. J. Org. Chem. 1988, 53, 286. For antiproliferative activity, see: ref li.
46. 7-PGA type compounds, see: (a) Kikuchi, H.; Tukitani, Y.; Iguchi, K.; Yamada, Y. Tetrahedron Lett. 1982, 23, 517. (b) Kobayashi, H.; Yasuzawa, T.; Yoshikawa, M.; Akatsu, H.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1982, 23, 5331. (c) Baker, B. J.; Okuda, R. K.; Yu, P. T.; Scheuer, P. J. J. Am. Chem. Soc. 1985, 107, 2976. See also: (d) Suzuki, M.; Morita, Y.; Yanagisawa, A.; Baker, B. J.; Scheuer, P. J.; Noyori, R. J. Org. Chem. 1988, 53, 286. For antiproliferative activity, see: ref li.
47. (a) Fitzpatrick, F. A.; Wynalda, M. A. J. Biol. Chem. 1983, 258, 11713.
48. (b) Kikawa, Y.; Narumiya, S.; Fukushima, M.; Wakatsuka, H.; Hayaishi, O. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 1317.
49. (c) Hirata, Y.; Hayashi, H.; Ito, S.; Kikawa, Y.; Ishibashi, M.; Suda, M.; Miyazaki, H.; Fukushima, M.; Narumiya, S.; Hayaishi, O. J. Biol. Chem. 1988, 263, 16619. See also: ref 3b.
50. (a) Ohno, K.; Fukushima, M.; Fujiwara, M.; Narumiya, S. J. Biol. Chem. 1988, 263, 19764.
51. (b) Santro, M. G.; Garaci, E.; Amici, C. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 8407.
52. (c) Koizumi, T.; Yamauchi, R.; Irie, A.; Negishi, M.; Ichikawa, A. Biochem. Pharmacol. 1991, 42, 777.
53. (d) Koizumi, T.; Negishi, M.; Ichikawa, A. Prostaglandins 1992, 43, 121.
54. (e) Amici, C.; Sistonen, L.; Santro, M. G.; Morimoto, R. I. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 6227.
55. (f) Amici, C.; Palamara, A. T.; Santro, M. G. Exp. Cell Res. 1993, 207, 230.
56. (g) Amici, C.; Giorgi, C.; Rossi, A.; Santro, M. G. J. Virol. 1994, 68, 6890.
57. (h) Santro, M. G. Experientia 1994, 50, 1039.
58. (i) Rossi, A.; Santro, M. G. Biochem. J. 1995, 308, 455.
59. (j) Koisumi, T.; Odani, N.; Okuyama, T.; Ichikawa, A.; Negishi, M. J. Biol. Chem. 1995, 270, 21779.
60. (a) Narumiya, S.; Fukushima, M. J. Pharmacol. Exp. Ther. 1986, 239, 500.
61. (b) Narumiya. S.; Ohno, K.; Fujiwara, M.; Fukushima, M. J. Pharmacol. Exp. Ther. 1986, 239, 506.
62. (c) Narumiya, S.; Ohno, K.; Fukushima, M.; Fujiwara, M. J. Pharmacol. Exp. Ther. 1987, 242, 306.
63. (d) Narumiya, S.; Fukushima, M. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 1987, 17, 972.
64. See also: (e) Narumiya, S.; Ohno, K.; Fukushima, M.; Fujiwara, M. In Prostaglandins in Cancer Research: Garaci, E., Paoletti, R., Santoro, M. G., Eds.; Springer-Verlag: Berlin, 1987; pp 86-96.
65. 2 has been proposed: Khan, S. H.; Sorof, S. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 9401.
66. Involvement of the GS-X pump has been suggested in the efflux of alkylating agents: (a) Ishikawa, T. Trend Biochem. Sci. 1992, 17, 463. (b) Ishikawa, T. In Structure and Function of Glutathione S-Transferases; Tew, K. D., Pickett, C. B., Mantle, T. J., Mannervik, B., Hayes, J., Eds.; CRC Press: Boca Raton, FL, 1993; pp 211-221. (c) Ishikawa, T.; Akimaru, K. In Glutathione S-Transferases: Structure, Function and Clinical Implications; Vermeulen, N. P. E., Mulder, G. J., Nieuwenhuyse, H., Peters, W. H. M., van Bladeren, P. J., Eds.; Tayler and Francis: London, 1996; pp 199-211.
67. Involvement of the GS-X pump has been suggested in the efflux of alkylating agents: (a) Ishikawa, T. Trend Biochem. Sci. 1992, 17, 463. (b) Ishikawa, T. In Structure and Function of Glutathione S-Transferases; Tew, K. D., Pickett, C. B., Mantle, T. J., Mannervik, B., Hayes, J., Eds.; CRC Press: Boca Raton, FL, 1993; pp 211-221. (c) Ishikawa, T.; Akimaru, K. In Glutathione S-Transferases: Structure, Function and Clinical Implications; Vermeulen, N. P. E., Mulder, G. J., Nieuwenhuyse, H., Peters, W. H. M., van Bladeren, P. J., Eds.; Tayler and Francis: London, 1996; pp 199-211.
68. Involvement of the GS-X pump has been suggested in the efflux of alkylating agents: (a) Ishikawa, T. Trend Biochem. Sci. 1992, 17, 463. (b) Ishikawa, T. In Structure and Function of Glutathione S-Transferases; Tew, K. D., Pickett, C. B., Mantle, T. J., Mannervik, B., Hayes, J., Eds.; CRC Press: Boca Raton, FL, 1993; pp 211-221. (c) Ishikawa, T.; Akimaru, K. In Glutathione S-Transferases: Structure, Function and Clinical Implications; Vermeulen, N. P. E., Mulder, G. J., Nieuwenhuyse, H., Peters, W. H. M., van Bladeren, P. J., Eds.; Tayler and Francis: London, 1996; pp 199-211.
69. Warning, A. J. Comprehensive Organic Chemistry; Stoddart, A. J., Ed.; Pergamon: Oxford, 1979; Vol. 1, Part 5.2, pp 1017-1104.
70. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
71. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
72. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
73. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
74. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
75. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
76. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
77. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
78. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
79. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
80. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
81. 2 (3), see: (l) Parker, J.; Ankel, H. Biochem. Pharmacol. 1992, 43, 1053.
82. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
83. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
84. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
85. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
86. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
87. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
88. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
89. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
90. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
91. For the reaction of thiols such as alkanethiols, glutathione, or cysteine with α,β-unsaturated ketones other than PGs. see: (chemical reactions under physiological conditions) (a) Esterbauer, H.; Zollner, H.; Scholz, N. Z. Naturforsch. 1975, 30C, 466. (b) Dimmock, J. R.; Smith, L. M.; Smith, P. J. Can. J. Chem. 1980, 58, 984. (enzymatic or biomimetic reactions), (c) Boyland, E.; Chasseaud, L. F. Biochem. J. 1968, 109, 651. (d) Boyland, E.; Chasseaud, L. F. In Advances in Enzymology; Nord, F. F., Ed.; Interscience Publishers: New York, 1969; Vol. 32, p 173. (e) Lillehang, J. R.; Kleppe, K.; Siegel, C. W.; Kapchan, S. M. Biochem. Biophys. Acta 1973, 327, 92. (f) Nicholas, A. W.; Rosazza, J. P. Bioorg. Chem. 1976, 5, 367. (g) Fujita, E.; Nagao, Y.; Kaneko, K.; Nakazawa, S.; Kuroda, H. Chem. Pharm. Bull. (Tokyo) 1976, 24, 2118. (h) Kapchan, S. M.; Siegel, C. W.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1976, 98, 2295. (i) Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O. J. Med. Chem. 1977, 20, 333. For the reaction of oridomin, enmein, and tenulin, see: (j) Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287.
92. For addition to the exocyclic double bond in a cross-conjugated dienone system, see: Siwapinyoyes, T.; Thebaranoth, Y. Tetrahedron Lett. 1984, 25, 353.
93. Reactions were performed under pseudo-second-order conditions with a large excess of phosphate buffer.
94. For involvement of sulfhydryl components in the binding with the target protein in the nuclei, see: Ohno, K.; Hirata, M. Biochem. Pharmacol. 1993, 46, 661.
95. Affinity Chromatography-Principles and Methods; Pharmacia Biotech.
96. Spragg, R. A. Appl. Spectrosc. 1984, 38, 604.
97. For the reversible reaction of Navelbine, an antitumor vinblastine analog, with the nucleophilic entity, see: (a) Potier, P. Pure Appl. Chem. 1986, 58, 737. (b) Potier, P. Semin. Oncol. 1989, 16, 2. For the reaction of leucodaunomycins, the intermediary compounds in the redox chemistry of an antitumor daunomycin, with cysteine derivatives, see: (c) Bird, D. M.; Gaudiano, G.; Koch, T. H. J. Am. Chem. Soc. 1991, 113, 308. See also: (d) Ishikawa, T.; Akimaru, K.; Kuo, M. T.; Priebe, W.; Suzuki, M. J. Natl. Cancer Inst. 1995, 87, 1639.
98. For the reversible reaction of Navelbine, an antitumor vinblastine analog, with the nucleophilic entity, see: (a) Potier, P. Pure Appl. Chem. 1986, 58, 737. (b) Potier, P. Semin. Oncol. 1989, 16, 2. For the reaction of leucodaunomycins, the intermediary compounds in the redox chemistry of an antitumor daunomycin, with cysteine derivatives, see: (c) Bird, D. M.; Gaudiano, G.; Koch, T. H. J. Am. Chem. Soc. 1991, 113, 308. See also: (d) Ishikawa, T.; Akimaru, K.; Kuo, M. T.; Priebe, W.; Suzuki, M. J. Natl. Cancer Inst. 1995, 87, 1639.
99. For the reversible reaction of Navelbine, an antitumor vinblastine analog, with the nucleophilic entity, see: (a) Potier, P. Pure Appl. Chem. 1986, 58, 737. (b) Potier, P. Semin. Oncol. 1989, 16, 2. For the reaction of leucodaunomycins, the intermediary compounds in the redox chemistry of an antitumor daunomycin, with cysteine derivatives, see: (c) Bird, D. M.; Gaudiano, G.; Koch, T. H. J. Am. Chem. Soc. 1991, 113, 308. See also: (d) Ishikawa, T.; Akimaru, K.; Kuo, M. T.; Priebe, W.; Suzuki, M. J. Natl. Cancer Inst. 1995, 87, 1639.
100. For the reversible reaction of Navelbine, an antitumor vinblastine analog, with the nucleophilic entity, see: (a) Potier, P. Pure Appl. Chem. 1986, 58, 737. (b) Potier, P. Semin. Oncol. 1989, 16, 2. For the reaction of leucodaunomycins, the intermediary compounds in the redox chemistry of an antitumor daunomycin, with cysteine derivatives, see: (c) Bird, D. M.; Gaudiano, G.; Koch, T. H. J. Am. Chem. Soc. 1991, 113, 308. See also: (d) Ishikawa, T.; Akimaru, K.; Kuo, M. T.; Priebe, W.; Suzuki, M. J. Natl. Cancer Inst. 1995, 87, 1639.
101. The dienone PGs should be substantially different from the common alkylating anticancer agents, which react with cellular nucleophiles in an irreversible manner.
102. (a) Ohno, K.; Hirata, M.; Narumiya, S.; Fukushima, M. Eicosanoids 1992, 5, 81.
103. See also: (b) Kosower, N. S.; Kosower, E. M. Int. Rev. Cytol. 1978, 54, 109.
104. (c) Meister, A.; Anderson, M. E. Annu. Rev. Biochem. 1983, 52, 711.
105. At this concentration of glutathione, the formation of the bisglutathione adduct 6f can be excluded on the basis of the kinetic and thermodynamic data.
106. This type of stabilization is reminiscent of the "message-address" concept which has been used for designing ligand molecules: (a) Schwyzer, R. Ann. N.Y. Acad. Sci. 1977, 297, 3. (b) Chavkin, C.; Goldstein, A. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6543. (c) Sayre, L. M.; Larson, D. L.; Takemori, A. E.; Portoghese, P. S. J. Med Chem. 1984, 27, 1325. (d) Takayanagi, I.; Konno, F.; Goromaru, N.; Koike, K.; Kanematsu, K.; Fujii, I.; Togame, H. Arch. Int. Pharmacodyn. 1988, 294, 71. For a review, see: (e) Kanematsu, K. Kagaku 1990, 45, 385, (in Japanese, Kagakudojin, Kyoto).
107. This type of stabilization is reminiscent of the "message-address" concept which has been used for designing ligand molecules: (a) Schwyzer, R. Ann. N.Y. Acad. Sci. 1977, 297, 3. (b) Chavkin, C.; Goldstein, A. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6543. (c) Sayre, L. M.; Larson, D. L.; Takemori, A. E.; Portoghese, P. S. J. Med Chem. 1984, 27, 1325. (d) Takayanagi, I.; Konno, F.; Goromaru, N.; Koike, K.; Kanematsu, K.; Fujii, I.; Togame, H. Arch. Int. Pharmacodyn. 1988, 294, 71. For a review, see: (e) Kanematsu, K. Kagaku 1990, 45, 385, (in Japanese, Kagakudojin, Kyoto).
108. This type of stabilization is reminiscent of the "message-address" concept which has been used for designing ligand molecules: (a) Schwyzer, R. Ann. N.Y. Acad. Sci. 1977, 297, 3. (b) Chavkin, C.; Goldstein, A. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6543. (c) Sayre, L. M.; Larson, D. L.; Takemori, A. E.; Portoghese, P. S. J. Med Chem. 1984, 27, 1325. (d) Takayanagi, I.; Konno, F.; Goromaru, N.; Koike, K.; Kanematsu, K.; Fujii, I.; Togame, H. Arch. Int. Pharmacodyn. 1988, 294, 71. For a review, see: (e) Kanematsu, K. Kagaku 1990, 45, 385, (in Japanese, Kagakudojin, Kyoto).
109. This type of stabilization is reminiscent of the "message-address" concept which has been used for designing ligand molecules: (a) Schwyzer, R. Ann. N.Y. Acad. Sci. 1977, 297, 3. (b) Chavkin, C.; Goldstein, A. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6543. (c) Sayre, L. M.; Larson, D. L.; Takemori, A. E.; Portoghese, P. S. J. Med Chem. 1984, 27, 1325. (d) Takayanagi, I.; Konno, F.; Goromaru, N.; Koike, K.; Kanematsu, K.; Fujii, I.; Togame, H. Arch. Int. Pharmacodyn. 1988, 294, 71. For a review, see: (e) Kanematsu, K. Kagaku 1990, 45, 385, (in Japanese, Kagakudojin, Kyoto).
110. This type of stabilization is reminiscent of the "message-address" concept which has been used for designing ligand molecules: (a) Schwyzer, R. Ann. N.Y. Acad. Sci. 1977, 297, 3. (b) Chavkin, C.; Goldstein, A. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6543. (c) Sayre, L. M.; Larson, D. L.; Takemori, A. E.; Portoghese, P. S. J. Med Chem. 1984, 27, 1325. (d) Takayanagi, I.; Konno, F.; Goromaru, N.; Koike, K.; Kanematsu, K.; Fujii, I.; Togame, H. Arch. Int. Pharmacodyn. 1988, 294, 71. For a review, see: (e) Kanematsu, K. Kagaku 1990, 45, 385, (in Japanese, Kagakudojin, Kyoto).
111. (a) Akimaru, K.; Kuo, M. T.; Furuta, K.; Suzuki, M.; Noyori, R.; Ishikawa, T. Cytotechnology 1996, 19, 221.
112. (b) 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., Mamett, L. J., Wong, P. Y-K., Eds.; Plenum Press: New York, 1996.
113. ATP-dependent transport of the PG-glutathione conjugate by the MRP/GS-X pump across the plasma membrane was verified by using the inside-out vesicles prepared from cisplatin-resistant HL-60 cells: Ishikawa, T.; Suzuki, M.; Furuta, K.; Noyori, R. Manuscript in preparation
114. The MRP/GS-X pump is overexpressed in this cell 4-5 times more than in usual HL-60 cells: (a) Ishikawa, T.; Wright, C. D.; Ishizuka, H. J. biol. Chem. 1994, 269, 29085. (b) Ishikawa, T.; Bao, J.-J.; Yamane, Y.; Akimaru, K.; Frindrich, K.; Wright, C. D.; Kuo, M. T. J. Biol. Chem. 1996, 271, 14981.
115. The MRP/GS-X pump is overexpressed in this cell 4-5 times more than in usual HL-60 cells: (a) Ishikawa, T.; Wright, C. D.; Ishizuka, H. J. biol. Chem. 1994, 269, 29085. (b) Ishikawa, T.; Bao, J.-J.; Yamane, Y.; Akimaru, K.; Frindrich, K.; Wright, C. D.; Kuo, M. T. J. Biol. Chem. 1996, 271, 14981.
116. Koizumi, T.; Negishi, M.; Ichikawa, A. Biochem. Pharmacol. 1992, 44, 1597.
117. 20
118. Elucidation of the molecular mechanism of the cancer cell growth inhibition effect by anticancer PGs, based on the use of 1 as an efficient biochemical probe for HL-60 human leukemia cells and cisplatin resistant HL-60/R-CP cells, has recently been reported. See: Reference 28b. Ishikawa, T.; Akimaru, K.; Nakanishi, M.; Suzuki, M.; Furuta, K.; Noyori, R. Submitted.
119. 1c
120. Peterson, M. R.; Poirier, R. A. University of Toronto. This program is based on parts of Pople's GAUSSIAN 80, QCPE 406, Indiana University, Bloomington, Ind.
121. (a) Hehre, W. J.; Stewart, R. F.; Pople, A. J. J. Chem. Phys. 1969, 51, 2657.
122. (b) Hehre, W. J.; Ditchfield, R.; Stewart, R. F.; Pople. J. A. J. Chem. Phys 1970, 52, 2769.
123. Taga, T.; Osaki, K.; Ito, N.; Fujita, E. Acta Crystallogr. 1582, B38, 2941.