Synthesis, topoisomerase I inhibitory activity and in vitro cytotoxicity of camptothecin derivatives bearing five-membered heterocycle containing 10-substituents

Anti-Cancer Drug Design

Volumn 13, Issue 2, 1998, Pages 145-157

  Zhao, Rulin ^a   Guan, Le Luo ^a   Oreski, Bernadette ^b   Lown, J William ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b NAEJA Pharmaceutical Inc   (Canada)

Author keywords

Camptothecin; DNA cleavage; Pyrrole compounds; Topoisomerase I

Indexed keywords

CAMPTOTHECIN DERIVATIVE; DNA; DNA TOPOISOMERASE; FURAN; PYRROLE; SINGLE STRANDED DNA; THIOPHENE;

AGAR GEL ELECTROPHORESIS; ARTICLE; CONTROLLED STUDY; DNA CLEAVAGE; DNA STRAND BREAKAGE; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL;

EID: 0031881501     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. ALLEY, M.C., SCUDIERO, D.A., MONKS, A., HURSEY, M.L., CZERWINSKI, M.J., FINC, D L., ABBOTT, B.J., MAYO, J.O., SHOEMAKER, R.H. & BOYD, M.R. (1986). Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Research, 48, 589.
2. 1H NMR and restrained (molecular dynamics simulation). Journal of the American Chemical Society, 117, 8917.
3. HERTZBERG, R.P., CARANFA, M.J., HOLDEN, K.G., JAKAS, D.R., GALLAGHER, H., MATTERN, M.R., MONG, S.M., BARTUS, J.O., JOHNSON, R.K & KINGSBURY, W.D. (1989). Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity. Journal of Medicinal Chemistry, 32, 715.
4. HERTZBERG, R.P., BUSBY, R.W., CARANFA. M.J , HOLDEN, K.G., JOHNSON, R.K., HECHT, S.M. & KINGSBURY, W.D. (1990). Irreversible trapping of the DNA-topoisomerase I covalent complex. Journal of Biological Chemistry, 265, 19287.
5. HSIANG, Y.H., HERTZBERG, R., HECHT, S. & LIU, L.F. (1985). Camptothecin induces protein-linked breaks via mammalian DNA topoisomerases. Annual Review of Biochemistry, 54, 665.
6. HSIANG, Y., LIU, L.F., WALL, M.E , WANI, M.C., NICHOLAS, A.W. MANIKUMAR, G., KIRSCHENBAUM, S., SILBER, R. & POTMESIL, M. (1989). DNA topoisomerase I-mediated DNA cleavage and cytotoxity of camptothecin analogs. Cancer Research, 49, 4385.
7. JAXEL, C., KOHN, K.W , WANI, M.C., WALL, M.E. & POMMIER, Y (1989). Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity. Cancer Research, 49, 1465.
8. JOHNSON, R K., MCCABE, F.L., FAUCETTE, L.F., HERTZBERG, R.P., KINGSBURY, W.D., BOEHM, J.C., CARANFA, M.J. & HOLDEN, K.G. (1989). SK&F 10864, a water-soluble analog of camptothecin with broad- spectrum activity in preclinical tumor models. Proceedings of the American Association of Cancer Research, 30, 623.
9. KUNIMOTO, T., NITTA, K., TANAKA, T., UEHARA, N., BABA, H., TAKEUCHI, M., YOKOKURA, T., SAWADA, S., MIYASAKA, T. & MUTAI, M. (1987). Antitumor activity of 7-ethyl-10-[4(1-piperidino)-1-piperidino]-carbonyloxy-camptothecin, a novel water-soluble derivative of camptothecin, against murine tumors. Cancer Research, 47, 5944.
10. LIU, L.F. (1989). DNA topoisomerase poisons and antitumor drug. Annual Review of Biochemistry, 58, 371.
11. MANIATIS, T., FRITSCH, E.F. & SAMBROOK, J. (1982). Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY.
12. POMMIER Y. (1993). DNA topoisomerase I and II in cancer chemotherapy: update and perspectives. Cancer Chemotherapy and Pharmacology, 32, 103.
13. POMMIER, Y. & TANIZAWA, A. (1993). Mammalian DNA topoisomerase I and its inhibitors. In Cancer Chemotherapy. Hickman, J.A. & Tritton, T.R. (eds), p. 67. Blackwell Scientific Publications: Oxford.
14. RODRIGUEZ-CAMPOS, A., AZORIN, F & PORTUGAL, J. (1996). Influence of elsamicin A on the activity of mammalian topoisomerase I. Biochemistry, 35, 11177.
15. WALL, M.E. & WANI, M.C. (1993). Camptothecin and analogues. In Human Medicinal Agents from Plants. Kinghorn, A.D. & Balandrin, M.F. (eds), ACS Symposium Series 534, p. 149. American Chemistry Society: Washington, DC.
16. WALL, M.E , WANI, M.C., COK, C.E., PALMER, K.H., MCPHAIL, A T. & SIM, G A. (1966). Plant antitumor agents. I. the isolation and structure of camptothecin, a novel alkaloidal and tumor inhibitor from Camptotheca acuminata. Journal of the American Chemical Society, 88, 3888.
17. WANG, J.C. (1985). DNA topisomerases. Annual Review of Biochemistry, 54, 665.
18. XIE, O., GUPTA R., ATCHISON, K & LOWN, J.W. (1996). Bisindolylmaleimides linked to DNA minor groove binding lexitropsins: synthesis, inhibitory activity against topoisomerase I, and biological evaluation. Journal of Medicinal Chemistry, 39, 1049.
19. ZHAO, R., AL-SAID, N.H., STERNBACH, D.L & LOWN, J.W. (1997). Camptothecin and minor-groove binder hybrid molecules: synthesis, inhibition of topoisomerase I and anticancer cytotoxicity in vitro. Journal of Medicinal Chemistry, 40, 216.