Mechanism of hydrolysis of a novel indolocarbazole topoisomerase I inhibitor

European Journal of Pharmaceutical Sciences

Volumn 39, Issue 5, 2010, Pages 291-297

  Breslin, David ^a   Sato, Yuichi ^b   Karki, Shyam B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Hydrolysis; Indolocarbazole; Topoisomerase

Indexed keywords

6 FORMYLAMINO 12,13 DIHYDRO 1,11 DIHYDROXY 5H INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7(6H) DIONE 13 GLUCOSIDE; ACID ANHYDRIDE; ANTINEOPLASTIC AGENT; ANTINEOPLASTIC ALKALOID; DICARBOXYLIC ACID; DNA TOPOISOMERASE INHIBITOR; ED 110; REBECCAMYCIN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DEGRADATION KINETICS; DRUG DEGRADATION; DRUG HYDROLYSIS; DRUG SCREENING; DRUG STRUCTURE; PH; PRIORITY JOURNAL; ROOM TEMPERATURE; SHELF LIFE; THERMOSTABILITY;

CARBAZOLES; DNA TOPOISOMERASES, TYPE I; ELECTROPHORESIS, CAPILLARY; ENZYME INHIBITORS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS;

EID: 77549086577     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2009.12.001     Document Type: Article

References (12)

1. Akao A., Hiraga S., Iida T., Kamatani A., Kawasaki M., Mase T., Nemoto T., Stake N., Weissman S.A., Tschaen D.M., Rossen K., Petrillo D., Reamer R.A., and Volante R.P. Practical synthesis of a potent indolocarbazole-based, DNA topoisomerase inhibitor. Tetrahedron 57 (2001) 8917-8923
2. Bailly C., Qu X., Chaires J.B., Colson P., Houssier C., Ohkubo M., Nishimura S., and Yoshinari T. Substitution at the F-ring N-imide of the indolocarbazole antitumor drug NB-506 increases cytotoxicity, DNA binding, and topoisomerase I inhibition activities. J. Med. Chem. 42 (1999) 2927-2935
3. Cavazos C.M., Keir S.T., Yoshinari T., Bigner D.D., and Friedman H.S. Therapeutic activity of the topoisomerase I inhibitor J-107088 [6-N-(1-hydroxymethyla-2-hydroxy)ethylamino-12,13-dihydro-13-(β-d-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]-carbazole-5,7(6H)-dione] against pediatric and adult central nervous system tumor xenografts. Cancer Chemother. Pharmacol. 48 (2001) 250-254
4. In: Dean J.A. (Ed). Langes Handbook of Chemistry. 13th ed. (1985), McGraw Hill, New York
5. Gribble G.W., and Berthel S.J. Studies in Natural Products Chemistry vol. 12 (1993), Elsevier Science
6. In: Martin A.N. (Ed). Physical Pharmacy (1993), Lea and Febiger, Philadelphia
7. Ohkubo M., Nishimura T., Jona H., Honma T., and Morishima H. Practical synthesis of indolocarbazoles. Tetrahedron 52 (1996) 8099-8112
8. Ohkubo M., Nishimura T., Honma T., Nishimura I., Ito S., Yoshinari T., Arakawa H., Suda H., Morishima H., and Nishimura S. Synthesis and biological activities of NB-506 analogues: effects of the positions of two hydroxyl groups at the indole rings. Bioorg. Med. Chem. Lett. 9 (1999) 3307-3312
9. Ohkubo M., Nishimura T., Kawamoto H., Nakano M., Honma T., Yoshinari T., Arakawa H., Suda H., Morishima H., and Nishimura S. Synthesis and biological activities of NB-506 analogues modified at the glucose group. Bioorg. Med. Chem. Lett. 10 (2000) 419-422
10. Prudhomme M. Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents. Curr. Med. Chem. 7 (2000) 1189
11. Waterman K.C., Adami R.C., Alante K.M., Antipas A.S., Arenson D.R., Carrier R., Hong J., Landis M.S., Lombardo F., Shah J.C., Shavaev E., Smith S.W., and Wang H. Hydrolysis of pharmaceutical formulations. Pharm. Dev. Technol. 7 (2002) 113-146
12. Yoshinari T., Ohkubo M., Fukasawa K., Egashira S., Hara Y., Matsumoto M., Nakai K., Arakawa H., Morishima H., and Nishimura S. Mode of action of a new indolocarbazole anticancer agent, J-107088, targeting topoisomerase I. Cancer Res. 59 (1999) 4271-4275