E-ring conformation has a key role in cleavable complex formation: Homocamptothecin versus camptothecins

Journal of Molecular Structure

Volumn 651-653, Issue , 2003, Pages 55-65

  Chauvier, D ^a   Chourpa, I ^b   Maizieres, M ^a   Riou, J F ^a   Dauchez, M ^a   Alix, A J P ^a   Manfait, M ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UFR de Pharmacie   (France)

Author keywords

Camptothecin; DNA topoisomerase I anticancer drug complex; Homocamptothecin

Indexed keywords

CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; CARBOXYLIC ACID; DNA; DNA TOPOISOMERASE; HOMOCAMPTOTHECIN; LACTONE; UNCLASSIFIED DRUG;

COMPLEX FORMATION; CONFERENCE PAPER; DNA DRUG COMPLEX; DRUG CONFORMATION; DRUG STABILITY; DRUG STRUCTURE; HYDROXYLATION; MOLECULAR ECOLOGY; MOLECULAR MECHANICS; MOLECULAR MODEL; PH; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION;

EID: 18844482067     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(03)00100-5     Document Type: Conference Paper

References (35)

1. Y. Pommier, P. Pourquier, Y. Fan, D. Strumberg, Biochim. Biophys. Acta 1400 (1998) 83.
2. P. D'arpa, C. Beardmore, L.F. Liu, Cancer Res. 50 (1990) 6919.
3. R.P. Hertzberg, R.W. Busby, M.I.J. Caranfa, K.G. Holden, R.K. Johnson, S.M. Hecht, W.D. Kingsbury, J. Biol. Chem. 265 (1990) 19587.
4. R.P. Hertzberg, M.J. Caranfa, S.M. Hecht, Biochemistry 28 (1989) 4629.
5. Y.H. Hsiang, R. Hertzberg, S. Hecht, L.F. Liu, J. Biol. Chem. 260 (1985) 14873.
6. M. Lisby, B.O. Krogh, F. Boege, O. Westergaard, B.R. Knudsen, Biochemistry 37 (1998) 10815.
7. Y.H. Hsiang, L.F. Leroy, M.E. Wall, M.C. Wani, A.W. Nicholas, G. Manikumar, S. Kirschenbaum, R. Silber, M. Potmesil, Cancer Res. 49 (1989) 4385.
8. J. Fassberg, V. Stella, J. Pharm. Sci. 81 (1992) 676.
9. K. Akimoto, A. Kawai, K. Ohya, Chem. Pharm. Bull. 42 (1994) 2135.
10. O. Lavergne, L. Lesueur-Ginot, F. Pla Rodas, D.C.H. Bigg, Bioorg. Med. Chem. Lett. 7 (1997) 2235.
11. O. Lavergne, L. Lesueur-Ginot, F. Pla Rodas, P.G. Kasprzyk, J. Pommier, D. Demarquay, G. Prévost, G. Ulibarri, A. Rolland, A.-M. Schiano-Liberatore, J. Harnett, D. Pons, J. Camara, D.C.H. Bigg, J. Med. Chem. 41 (1998) 5410.
12. L. Lesueur-Ginot, D. Demarquay, R. Kiss, P. Kasprzyk, L. Dassoneville, C. Bailly, J. Camara, O. Lavergne, D.C.H. Bigg, Cancer Res. 59 (1999) 2939.
13. R.P. Hertzberg, M.J. Caranfa, K.G. Holden, R.J. Dalia, G. Gallagher, M.R. Mattern, S.-M. Mong, J. O'Leary Bartus, R.K. Johnson, W.D. Kingsbury, J. Med. Chem. 32 (1989) 715.
14. A.W. Nicholas, M.C. Wani, G. Manikumar, M.E. Wall, K.W. Kohn, Y. Pommier, J. Med. Chem. 33 (1990) 972.
15. M.R. Redinbo, L. Stewart, P. Kuhn, X. Qiu, J.J. Champoux, W.G.J. Hol, Science 279 (1998) 1504.
16. Y. Fan, J.N. Weinstein, K.W. Kohn, L.M. Shi, Y. Pommier, J. Med. Chem. 41 (1998) 2216.
17. J.E. Kerrigan, D.S. Pilch, Biochemistry 40 (2001) 9792.
18. I. Chourpa, J.-F. Riou, J.-M. Millot, Y. Pommier, M. Manfait, Biochemistry 37 (1998) 7584.
19. D. Yang, J.T. Strode, H.P. Spielmann, A.H.P. Wang, T.G. Burke, J. Am. Chem. Soc. 120 (1998) 2979.
20. S. Yao, D. Murali, P. Seetharamulu, K. Haridas, N.V. Petluru, D.G. Reddy, F.H. Hausheer, Cancer Res. 58 (1998) 3782.
21. I. Chourpa, J.-F. Riou, Y. Pommier, M. Manfait, in: P. Carmona, et al. (Eds.), Spectroscopy of Biological Molecules: Modern Trends, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1997, p. 361.
22. Y. Pommier, A. Tanizawa, K.W. Kohn, Adv. Pharmacol 29B (1994) 73.
23. I. Chourpa, J.-M. Millot, G.D. Sockalingum, J.-F. Riou, M. Manfait, Biochim. Biophys. Acta 1379 (1998) 353.
24. C. Jaxel, G. Capranico, D. Kerrigan, K.W. Kohn, Y. Pommier, J. Biol. Chem. 266 (1991) 20418.
25. MSI/Accelrys, 9685 Scranton Road, San Diego, CA 92121- 2777, USA.
26. I. Nabiev, F. Fleury, I. Kudelina, Y. Pommier, F. Charton, J.-F. Riou, A.J.P. Alix, M. Manfait, Biochem. Pharmacol. 55 (1998) 1163.
27. J.R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New-York, 1983, Chapter 7, p 187.
28. Z. Mi, T.G. Burke, Biochemistry 33 (1994) 10325.
29. S. Coderoni, M. Paparelli, G.L. Gianfranceschi, Mol. Biol. Rep. 14 (1990) 255.
30. K. Christiansen, B.R. Knudsen, O. Westergaard, J. Biol. Chem. 269 (1994) 11367.
31. M. Gigli, S. Doglia, J.-M. Millot, L. Valentini, M. Manfait, Biochem. Biophys. Acta 950 (1988) 13.
32. S.E. Miller, D.S. Pilch, Ann. N.Y. Acad. Sci. 922 (2000) 309.
33. G.S. Laco, J.R. Collins, B.T. Luke, H. Kroth, J.M. Sayer, D.M. Jerina, Y. Pommier, Biochemistry 41 (2002) 1428.
34. X. Wang, X. Zhou, S. Hecht, Biochemistry 38 (1999) 4374.
35. W. Du, D.P. Curran, R.L. Bevins, S.G. Zimmeer, J. Zhang, T.G. Burke, Bioorg. Med. Chem. Lett. 10 (2002) 103.