Camptothecin and derivatives: A new class of antitumor agents;Camptothecine et derives: Une nouvelle classe d'agents antitumoraux

Journal de Pharmacie de Belgique

Volumn 51, Issue 4, 1996, Pages 200-207

  Torck, Monique ^a   Pinkas, Madeleine ^a  

^a UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; DNA TOPOISOMERASE; IRINOTECAN; TOPOTECAN; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE;

ANEMIA; ANTINEOPLASTIC ACTIVITY; CANCER; CYTOTOXICITY; DIARRHEA; DRUG INFORMATION; DRUG MECHANISM; HEMORRHAGIC CYSTITIS; HUMAN; NEUTROPENIA; REVIEW; STRUCTURE ACTIVITY RELATION; THROMBOCYTOPENIA; ANIMAL;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; HUMANS;

EID: 0030183751     PISSN: 00472166     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (82)

1. KOCH M. Principaux anticancéreux d'origine végétale. C.R Soc. Biol. 1992, 186, 441-457.
2. TOSCO C., LINDLEY C. Vinorelbine: a novel vinca alkaloid. Am. J. Health-Syst Pharm. 1995, 52, 1287-1303.
3. VANHAELEN M.H. Le taxol et les diterpenoïdes apparentés de Taxus sp : acquisitions importantes dans la chimiothérapie du cancer. J. Pharm. Belg. 1992, 47, 417-424.
4. GUÉRITE-VOEGELEIN F., GUÉNARD D., DUBOIS J., WAHL A., POTIER P. Recherche chimique et biologique autour du Taxol® (Paclitaxel) et du Taxotëre® (Docetaxel), nouveaux agents antitumoraux. J. Pharm. Belg. 1994, 49, 193-205.
5. JONES A.L., SMITH I.E. The taxanes. Cancer Topics 1994, 9, 10-13.
6. MADELAINE I, FAURE P. Paclitaxel et docetaxel : une nouvelle classe d'agents anticancéreux. J. Pharm. Clin. 1994, 13, 9-16.
7. WALL M.E., WANI M.C. Camptothecin and taxol : discovery to clinic - Thirteenth Bruce F. Cain Memorial Award lecture. Cancer Res.1995, 55, 753-760.
8. WALL M.E., WANI M.C. In "Medicinal chemistry" Camptothecin, Ed. J.M. CASSADY et J.D. DOUROS, Academic Press. New York, London, 1980, vol. 16, 417-436.
9. WALL M.E., WANI M.C., COOK C.E., PALMER K.H., Mc PHAIL A.T., SIM G.A. Plant antitumor agents. I. The isolation and structure of camptothecin a novel alkaloid leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc. 1966, 88, 3888-3890.
10. HSIANG Y.H., HERTZBERG R., HECHT S., LIU L.F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerases I. J. Biol. Chem. 1985, 260, 14873-14878.
11. DECAISNE M.J. Caractères et descriptions de trois genres nouveaux de plantes recueillies en Chine par l'abbé A. David. Bull. Soc. Bot. de France 1873, 20, 155-159.
12. HEYWOOD V.H. Flowering plants of the world, Ed. by B.T. BATSFORD, London, 1993.
13. HUTCHINSON C.R. Camptothecin: chemistry, biogenesis and medicinal chemistry. Tetrahedron 1981, 31, 1065-1081.
14. TANG W., EISENBRAND G. Chinese drugs of plant origin, Ed. Springer, Berlin, Heidelberg, 1992, 239-261.
15. WANI M.C., WALL M.E. Plant antitumor agents. II. The structure of two new alkaloids from Camptotheca acuminata. J. Org. Chem. 1969, 34, 1364-1367.
16. ADAMOVICS S.A., CINA J.A., HUTCHINSON C.R. Minor alkaloids of Camptotheca acuminata. Phytochemistry 1979, 18, 1085-1086.
17. LOPEZ-MEYER M., NESSLER C.L., Mc KNIGHT T.D. Sites of accumulation of the antitumor alkaloid camptothecin in Camptotheca acuminata. Planta Med. 1994, 60, 558-560.
18. BROGLIA S., VEROTTA L., BATTISTINI M. Application of high speed countercurrent chromatography to the separation of camptothecin and 9-methoxycamptothecin. Fitoterapia 1994. 65, 520-523.
19. GOVINDACHARI, T. R., VISWANATHAN N. 9-methoxycamptothecin, new alkaloid from Mappia foetida Miers. Indian J. Chem. 1972, 10, 453-454.
20. TAFUR S., NELSON J.D., De LELONG C., SVOBODA H. Antiviral components of Ophiorrhiza mungos : isolation of camptothecin and 10-methoxycamptothecin. Lloydia 1976, 39, 261-262.
21. GUNASEKERA P., BADAWI M., CORDELL A., FARNSWORTH R. Plant anticancer agents. X. Isolation of camptothecin and 9-methoxycamptothecin from Ervatemia heyneana. R.S. Natural Prod. 1979, 42, 475-477.
22. RIVORY L.P., ROBERT J. Pharmacologie de la camptothécine et de ses dérivés. Bull. Cancer 1995, 82, 265-285.
23. STORK G., SCHULTZ A.C. The total synthesis of dl-camptothecin. J. Am. Chem. Soc. 1971, 33, 4074-4075.
24. COREY E.J., CROUSE D.N., ANDERSON J.E. A total synthesis of natural 20(S)-camptothecin. J. Org. Chem. 1975, 20, 2140-2141.
25. WANI M.C., ROUMAN P.E., LINDLEY J.T., WALL M.E. Plant antitumor agents. XVIII. Synthesis and biological activity of camptothecin analogs. J. Med. Chem. 1980, 23, 554-560.
26. SCHEN W., COBURN C.A., BORNMANN W.G., DANISHEFSKY S.J. Concise total synthesis of dl-camptothecin and related anticancer drugs. J. Org. Chem. 1993, 58, 611-617.
27. LUZZIO M.J., BESTERMAN J.M., EVANS M.G., LACKEY K.E., LEITNER P., PEEL M.R., SISCO J.M. Novel water soluble camptothecin analogs as inhibitors of topoisomerase I. Proc. Am. Assoc. Cancer Res. 1993, 34, A 1980.
28. CREEMERS G.J., LIND B., VERWEIJ J. Topoisomerase I inhibitors : topotecan and irinotecan. Cancer Treat. Rev. 1994, 20, 73-96.
29. O'DWYER P.J., La CRETA F.P., HAAS N.B., HALBHERR T., FRUCHT H., GOOSENBERG E., YAO K.S. Clinical pharmacokinetic and biological studies of topotecan. Cancer Chemother. Pharmacol. 1994, 34 (Suppl.), 546-552.
30. LAKEY K., BESTERMAN J.M., FLETCHER W., LEITNER P., MORTON B., STERNBACH D.D. Rigid analogs of camptothecin as DNA topoisomerase I inhibitors. J. Med. Chem. 1995, 38, 906-911.
31. HERTZBERG R.P., CARANFA M.J., HOLDEN K.J., JAKAS D.R., GALLAGHER G., MATTERN M.P., MONG S.M., BARTUS J.O., JOHNSON R.K., KINGSBURY W.D. Modification of the hydroxy lactone ring of camptothecin. Inhibition of mammalian topoisomerase I and biological activity. J. Med. Chem. 1989, 32, 715-720.
32. JAXEL C., KOHN K.W., WANI M.C., WALL M.E., POMMIER Y. Structure activity study of the actions of camptothecin derivatives on mammalian topoisomerase I and biological activity. J. Med. Chem. 1989, 32, 715-720.
33. FASSBERG J., STELLA V.J. Kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. J. Pharm. Sci. 1992, 81, 676-684.
34. AKIMOTO K., KAWAI A., OHYA K. Kinetics studies of the hydrolysis and lactonization of camptothecin and its derivatives, CPT-11 and SN-38, in aqueous solution. Chem. Pharm. Bull. 1994, 42, 2135-2138.
35. SLICHENMYER J.W., ROWINSKY E.K., DONEHOWER R.C., KAUFMANN S.N. The current status of camptothecin analogues as antitumor agents. J. Natl. Cancer Inst. 1993, 85, 271-291.
36. WALL M.E., WANI M.C., NICHOLAS A.W., MANIKUMAR G., TELE C., MOORE L., TRUESDALE A., LEITNER P., BESTERMANN J.M. Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogues. J. Med. Chem. 1993, 36, 2689-2700.
37. KINGSBURY W.D., BOEHM J.C., JAKAS R.D., HOLDEN K.G., HECHT S.M., GALLACHER G., CARANFA M.J., Mc CABE F.L., FAUCETTE L.F., JOHNSON R.K., HERTZBERG R.P. Synthesis of water soluble (aminoalkyl) camptothecin analogues : inhibition of topoisomerase I and antitumor activity J. Med. Chem. 1991, 34, 98-107.
38. SAWADA S., OKAJIMA S., AIYAMA R., NOKATA K., FURUTA T., OKOKURA T., SUGINO E., YAMAGUCHI K., MIYASAKA T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives : carbamate linked, water-soluble derivatives of 7-ethyl-10-hydroxy-camptothecin. Chem. Pharm. Bull. 1991, 39, 1446-1454.
39. LUZZIO M.J., BESTERMAN J.M., EMERSON D.L., EVANS M.G., LACKEY K., LEITNER P.L., Mc INTYRE G., MORTON R., MYERS P.L., PEEL M., SISCO J.M., STERNBACH D.D., TONG W.Q., TRUESDALE A., UEHLING D.E., VUONG A., YATES J. Synthesis and antitumor activity of novel water soluble derivatives of camptochecin as specific inhibitor of topoisomerase I. J. Med. Chem. 1995, 38, 395-401.
40. EMERSON D.L., BESTERMAN J.M., BROWN R.J., EVANS M.G., LEITNER P.P., LUZZIO M.J., SHAFFER J.E., STERNBACH D.D., UEHLING D.E., VUONG A. In vivo antitumor activity of two new seven-substituted water soluble camptothecin analogues. Cancer Res. 1995, 55, 603-609.
41. SAWADA S., YAEGASHI T., FURUTA T., YOKOKURA T., MIYASAKA T. Chemical modification of an antitumor alkaloid 20(S)-camptothecin E-lactone ring-modified water soluble derivatives of 7-ethylcamptothecin. Chem. Pharm. Bull 1993, 41, 310-313.
42. YAEGASHI T., SAWADA S., NAGATA H., FURUTA T., YOKOKARA T., MIYASAKA T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-nng-subslituted 7-éthykamptothecins and their E-ring. Modified water-soluble derivatives. Chem. Pharm. Bull. 1994, 42, 2518-2525.
43. WANG H.K., LIU S.Y., HWANG K.M., Mc PHAIL A.T., LEE K.H. The synthesis of 5-substituted camptothecins as potential inhibitors of DNA Topoisomerase I. Bioorg. Med. Chem. Lett. 1995, 5, 77-82.
44. HSIANG Y.H., LIHOU M.G., LIU L.F. Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin. Cancer Res. 1989, 49, 5077-5082.
45. WANG J.C. Les enzymes qui modifient la topologie de l'ADN. Pour la Science 1982, no 59, 56-71.
46. MADELAINE I., FAURE P. Les topoisomérases : nouvelles cibles pharmacologiques d'agents anticancéreux. J. Pharm. Clin. 1993, 12, 169-175.
47. Dossier Campto®. Laboratoire R.P. Bellon.
48. WANG J. DNA topoisomerase. Annu. Rev. Biochem. 1985, 54, 665-697.
49. HSIANG Y.M., LIU L.F., HOCHSTER H., POTMESIL M. Levels of DNA topoisomerase I (Topo-I) and topoisomerase II (Topo-II) in human colorectal carcinoma and normal colonie mucosa. Proc. Am. Assoc. Cancer Res. 1988, 29, 172.
50. POTMESIL M., HSIANG Y.M., LIU L.F., KNOWLES D., KIRSCHENBAUM S., TRAGANOS F., SILBER R. Topoisomerase I (Topo-I) and topoisomerase II (Topo-II) levels in high and low grade lymphomas. Proc. Am. Assoc. Cancer Res. 1988, 29, 176.
51. ARMAND J.P., DUCREUX M., MAHJOUBI M., ABIGERGES D., BUGAT R., CHABOT G., HERAIT P., FURNI M., ROUGIER P. CPT-11 (irinotécan) dans le traitement du cancer colorectal. Eur. J. Cancer 1985, 31, 1283-1287.
52. MATTERN M.R., MONG S.M., BARTHUS H.F., MIRABELLI C.K., CROOKE S.T., JOHNSON R.K. Relationship between the intracellular effects of camptothecin and the inhibition of topoisomerase I in cultured L 1210 cells. Cancer Res. 1987, 47, 1793-1798.
53. HERTZBERG R.P., CARANFA M.J., HECHT S. On the mechanism of topoisomerase I inhibition by camptothecin : evidence for binding to an enzyme-DNA complex. Biochemistry 1989, 28, 4629-4638.
54. ANDON T., ISHII K., SUZUKI Y., IKEGAMI Y., KUSUNOKI Y., TAKEMOTO Y., OKADA K. Characterization of a mammalian with camptothecin-resistant DNA topo-isomerase I. Proc. Natl. Acad. Sci. 1987, 84, 5565-5569.
55. PEREGO P., CAPRANICO G., SUPINO R., ZUNINO F. Topoisomerase I gene expression and cell sensitivy to camptothecin in human cell lines of different tumor types. Anticancer Drugs 1994, 5, 645-649.
56. CHEN A.Y., YU C., POTMESIL M., WALL M.E., WANI M.C., LIU L.F. Camptothecin overcomes MDR1-mediated resistance in human KB carcinoma cells. Cancer Res. 1991, 51, 6039-6044.
57. HENDRICKS C.B., ROWINSKY E.K., GROCHOW L.B., DONEHOWER R.C., KAUFMANN S.H. Effect of P-glycoprotein expression on the accumulation and cytotoxicity of topotecan (SKF 104864), a new camptothecin analogue. Cancer Res. 1992, 52, 2268-2278.
58. ABIGERGES D., CHABOT G.G., ARMAND J.P., HERAIT P., GOUYETTE A., GANDIA D. Phase I and pharmacologic studies of the camptothecin analogue irinotecan administred every three weeks in patients with advanced solid tumours. J. Clin. Oncol. 1995, 13, 210-221.
59. POTMESIL M. Camptothecins : from bench research hospital wards. Cancer Res. 1994, 54, 1431-1439.
60. BETCHER D.L., BURNHAM N. Topotecan. J. Ped. Oncol. Nursing 1994, 9, 31-32.
61. CHABOT G.G., ABIGERGES D., CATIMEL G., CULINE S., FORNI M., EXTRA J.M., MAHJOUBI M., HERAIT P., ARMAND J.P., BUGAT R., CLAVEL M., MARTY M.E. Population pharmacokinetics and pharmacodynamics of irinotecan (CPT-11) and active metabolite SN-38 during phase I trials. Annals of Oncol 1995, 6, 141-151.
62. BURKET G., MUNSHI C.B., MI Z., JIANG Y. The important role of albumine in determining the relative human blood stabilities of the camptothecin anticancer drugs. J. Pharm. Sci. 1995, 84, 518-519.
63. BURRIS H.A., ROTHENBERG M.L., KUHN J.G., Von HOFF D.D. Clinical trials with the topoisomerase I inhibitors. Seminars in Oncology 1992, 19, 663-669.
64. Van WARMERDAM L.J.C., VERWEIJ J., SCHELLENS J.H.M., ROSING H., BOER-DENNERT B.E.D., MAES R.A.A., BEIJNEN J.H. Pharmacokinetics and pharmacodynamics of topotecan administered daily for 5 days every 3 weeks. Cancer Chemother. Pharmacol. 1995, 35, 237-245.
65. HAAS N.B., La CRETA F.P., WALCZAK J., HUDES G.R., BRENNAN J.M., OZOLS R.F., O'DWYER P.J. Phase 1/Pharmacokinetic study of topotecan by 24-hours continuous infusion weekly. Cancer Res. 1994, 54, 1220-1226.
66. MOERTEL C.G., SCHUTT A.J., REITEMEIER R.J., HAHN R.G. Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer. Cancer Chemother. Rep. 1972, part 1, 56, 95-101.
67. MUGGIA F.M.;, CREAVEN P.J., HANSEN H.H., COHEN M.H., SELAWRY O.S. Phase I clinical trial of weekly and daily treatment with camptothecin (NSC-100880) : correlation with preclinical studies. Cancer Chemother. Rep. 1972, part 1, 56, 515-521.
68. KAWATO Y., FURUTA T., AONUMA M., YASUOKA M., YOKOKURA T., MATSUMOTO K. Antitumor activity of a camptothecin derivative, CPT-11, against human tumor xenografts in nude mice. Cancer Chemother.Pharmacol. 1991, 28, 192-198.
69. DAOUD S., FETOUH M.I., GIOVANELLA B.C. Antitumor effect of liposome-incorporated camptothecin in human malignant xenografts. Anti-Cancer Drugs 1995, 6, 83-93.
70. PRATESI G., TORTORETO M., CORTI C., GIARDINI R., ZUNINO F Successful local regional therapy with topotecan intraperitoneally growing human ovarian carcinoma xenografts. Br J. Cancer 1995, 71, 525-528.
71. HOUGHTON P.J., CHESHIRE P.J., HALLMAN J.D., LUTZ L., FRIEDMAN H.S., DANKS M.K., HOUGHTON J.A. Efficacy of topoisomerase I inhibitors, topotecan and irinotecan, administered at low dose levels in protracted schedules to mice bearing xenografts of human tumors. Cancer Chemother. Pharmacol. 1995, 36, 393-403.
72. HONO R., OKADA K., MASAOKA T., KURAMOTO A., ARIMA T., YOSHIDA Y., ARIYOSHI H., ICHIMARU M., SAKAI Y., OGURO M., ITO Y., MORISHIMA Y., YOKOMAKU S., OTA K. An early phase II study of CPT-11 : a new derivative of camptothecin, for the treatment of leukemia and lymphoma. J. Clin. Oncol. 1990, 8, 1907-1912.
73. SHIMADA Y., YASHINO M., WAKUI A., NAKAO I., FUTATSUKI K., SAKATO Y., KAMBE M., TAGUCHI T., OGAWA T. Phase II study of CPT-11, a new camptothecin derivative, in metastatic colorectal cancer. J. Clin. Oncol. 1993, 11, 909-913.
74. GROCHOW L.B., ROWINSKY E.K., JOHNSON R., LUDEMAN S., KAUFMANN S.H., Mc CABE F.L., SMITH B.R., HUROWITZ L. De LISA A., DONEHOWER R.C., NOE D.A. Pharmacokinetics and pharmacodynamics of topotecan in patients with advanced cancer. Drug Metab. Disposition 1992, 20, 706-713.
75. BURRIS H.A., AWADA A., KUHN J.G., ECKARDT J.R., COBB P.W., RINALDI D.A., FIELDS S., SMITH L. Von HOFF D.D. Phase I and pharmacokinetics studies of topotecan administered as a 72 or 120 h continuous infusion. Anti-Cancer Drugs 1994, 5, 394-402.
76. BAUER R. Chinesische Arzneidrogen als Quelle neuer Arzneistoffe für die Westliche Medizin. Pharmazie in unserer Zeit. 1994, 23, 291-300.
77. HELLWIG B. Topoisomerase-I-Inhibitoren Irinotecan und Topotecan. Deutsche Ap. Ztg 1996, 136, 261-262.
78. BAKER S.D., HEIDEMAN R.L., CROM W.R., KUTTESCH J.F., GAJJAR A., STEWART C.F. Cerebral spinal fluid pharmacokinetics and penetration of continuous infusion topotecan in children with central nervous system tumors. Cancer Chemother Pharmacol. 1996, 37, 195-202.
79. BLANEY S.M., COLE D.E., GODWIN K., SUNG C., POPLACK D.G., BALIS EM. Intrathecal administration of topotecan in non human primates. Cancer Chemother. Pharmacol. 1995, 36, 121-124.
80. MASUDA N., FUKUOKA M., TAKADA M , KUSUNOKI Y., NEGORO S.;, MATSUI K., KUDON S., TAKIFUJI N., NAKAKAWA K., KISHIMOTO S. CPT-11 in combinaison with cisplatine for advanced non-small-cell luny cancer. J. Clin. Oncol. 1992, 10, 1775-1780.
81. KAUFMAN S.M. Antagonism between camptothecin and topoisomerase II directed chemotherapeutic agent in a human leukemia cell line. Cancer Res. 1991, 51, 1129-1136.
82. BERTRAND R., O'CONNOR P., KERRIGAN D., POMMIER Y. Sequential administration of camptothecin and etoposide circumnents the antagonistic cytotoxicity of simultaneous drug administration in slowly growing human colon carcinoma HT-29 cells. Eur. J. Cancer 1992, 28 A, 743-748.