The other comptothecins: Recent advances on camptothecin analogs other than irinotecan and topotecan;Les autres camptothecines: Avancees recentes sur les analogues de la camptothecine autres que l'irinotecan et le topotecan

Bulletin du Cancer

Volumn 85, Issue SPEC. ISS. DEC., 1998, Pages 51-58

  Lavergne, Olivier ^a   Bigg, Dennis C H ^a  

^a Institut Henri Beaufour   (France)

Author keywords

Analogs; Camptothecin; Clinical trials; Derivatives; Structure activity

Indexed keywords

9 AMINOCAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; EXATECAN; IRINOTECAN; LURTOTECAN; TOPOTECAN; UNCLASSIFIED DRUG; 9 AMINO 20 CAMPTOTHECIN; 9-AMINO-20-CAMPTOTHECIN; 9-NITROCAMPTOTHECIN; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; DNA TOPOISOMERASE; DRUG DERIVATIVE; ENZYME INHIBITOR; PRODRUG; RUBITECAN; TUMOR PROTEIN;

ANTINEOPLASTIC ACTIVITY; CANCER; CANCER CHEMOTHERAPY; CLINICAL TRIAL; DRUG EFFICACY; DRUG RESEARCH; DRUG STRUCTURE; HUMAN; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; DRUG SCREENING; MACROMOLECULE; MOUSE;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; DNA TOPOISOMERASES, TYPE I; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; MACROMOLECULAR SUBSTANCES; MICE; MOLECULAR STRUCTURE; NEOPLASM PROTEINS; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032249641     PISSN: 00074551     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (63)

1. Wall ME, Wani MC. Camptothecin and analogs : from discovery to clinic. In : Potmesil M, Pinedo HM. Camptothecins : new anticancer agents. CRC Press : Boca Raton (FI), 1995 ; 21-41.
2. Rothenberg ML. Topoisomerase I inhibitors : review and update. Ann Oncol 1997 ; 8 : 837-55.
3. Wang HK, Morris-Natschke SL, Lee KH. Recent advances in the discovery and development of topo-isomerase inhibitors as antitumor agents. Med Res Rev 1997 ; 17 : 367-425.
4. Takimoto CH, Arbuck SG. Clinical status and optimal use of topotecan. Oncology (Huntingt) 1997 ; 11 : 1635-46.
5. Muggia FM. Twenty years later : review of clinical trials with camptothecin sodium. In : Potmesil M, Pinedo HM. Camptothecins : new anticancer agents. CRC Press : Boca Raton (FI), 1995 ; 43-50.
6. Natelson EA, Giovanella BC, Verschraegen CF, Fehir KM, De Ipolyi PD, Harris N, et al. Phase I clinical and pharmacological studies of 20-(S)-camptothecin and 20-(S)-9-nitrocamptothecin as anticancer agents. Ann NY Acad Sci 1996 ; 803 : 224-30.
7. Wani MC, Nicholas AW, Manikumar G, Wall ME. Plant antitumor agents, 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations. J Med Chem 1987 ; 30 : 1774-9.
8. Potmesil M, Arbuck SG, Takimoto CH, Liebes L, Hochster H. 9-Aminocamptothecin and beyond. Preclinical and clinical studies. Ann NY Acad Sci 1996 ; 803 : 231-46.
9. Jaxel C, Kohn KW, Wani MC, Wall ME, Pommier Y. Structure-activity study of the actions of camptothecin derivatives on mammalian topo-isomerase I : evidence for a specific receptor site and a relation to antitumor activity. Cancer Res 1989 ; 49 : 1465-9.
10. Giovanella BC, Stehlin JS, Wall ME, Wani MC, Nicholas AW, Liu LF, et al. DNA topo-isomerase I targeted chemotherapy of human colon cancer in xenografts. Science 1989 ; 246 : 1046-8.
11. Chen AY, Yu C, Potmesil M, Wall ME, Wani MC, Liu LF. Camptothecin overcomes MDR1-mediated resistance in human KB carcinoma cells. Cancer Res 1991 ; 51 : 6039-44.
12. Rubin E, Wood V, Bharti A, Trites D, Lynch C, Hurwitz S, et al. A phase I and pharmacokinetic study of a new camptothecin derivative, 9-aminocamptothecin. Clin Cancer Res 1995 ; 1 : 269-76.
13. Eder JP Jr, Supko JG, Lynch T, Bryant M, Vosburg E, Shulman LN, et al. Phase I trial of the colloidal dispersion formulation of 9-amino-20(S)-camptothecin administered as a 72-hour continuous intravenous infusion. Clin Cancer Res 1998 ; 4 : 317-24.
14. Dahut W, Harold N, Takimoto C, Allegra C, Chen A, Hamilton JM, et al. Phase I and pharmacologic study of 9-aminocamptothecin given by 72-hour infusion in adult cancer patients. J Clin Oncol 1996 ; 14 : 1236-44.
15. Pitot H, Knost JA, Mahoney MR, O'Connell MJ, Krook J. A phase II trial of 9-amino-20(S)-camptothecin (9-AC) in previously untreated patients with measurable metastatic colorectal carcinoma. Proc Am Soc Clin Oncol 1997 ; 16 (abst. 1077).
16. Kraut EH, Balcerzak SP, O'Rourke MA, Petrus J, Mayernik D. Phase II trial of 9-aminocamptothecin in patients with refractory breast cancer. Proc Am Soc Clin Oncol 1997 ; 16 (abst. 620).
17. Wilson WH, Elwood P, Little R, Pearson D, Humphrey R, Raffeld M, et al. A phase II and dose escalation study of 9-amino-camptothecin (9-AC) ± G-CSF in relapsed lymphoma. Proc Am Soc Clin Oncol 1997 ; 16 (abst. 139).
18. Saltz LB, Kemeny NE, Tong W, Harrison J, Berkery R, Kelsen DP. 9-aminocamptothecin by 72-hour continuous Intravenous infusion is inactive in the treatment of patients with 5-fluorouracil-refractory colorectal carcinoma. Cancer 1997 ; 80 : 1727-32.
19. Hinz HR, Harris NJ, Natelson EA, Giovanella BC. Pharmacokinetics of the in vivo and in vitro conversion of 9-nitro-20(S)-camptothecin to 9-amino-20(S)-camptothecin in humans, dogs, and mice. Cancer Res 1994 ; 54 : 3096-100.
20. Verschraegen C, Giovanella B, Armstrong K, Kavanagh J, Kudelka A, Steger M, et al. Phase II study of oral administration of 9-nitrocamptothecin (9NC) in refractory ovarian cancer. Proc Am Soc Clin Oncol 1997 ; 16 (abst. 1356).
21. Luzzio MJ, Besterman JM, Emerson DL, Evans MG, Lackey K, Leitner PL, et al. Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topo-isomerase I. J Med Chem 1995 ; 38 : 395-401.
22. Besterman JM. Topoisomerase I inhibition by the camptothecin analog GI147211C. From the laboratory to the clinic. Ann NY Acad Sci 1996 ; 803 : 202-9.
23. Van Oosterom AT, Gore M, Calvert AH, Ten Bokkel Huinink WW, Hansen HH, Wissel P, et al. Activity of GW211 (GI 147211) in relapsed ovarian cancer, a phase II study [abstract]. Proc Am Soc Clin Oncol 1997 ; 16 (abst. 1250).
24. Gerrits CJ, Schellens JH, Creemers GJ, Wissel P, Planting AS, Pritchard JF, et al. The bioavailability of oral GI147211 (GG211), a new topo-isomerase I inhibitor. Br J Cancer 1997 ; 76 : 946-51.
25. Sugimori M, Ejima A, Ohsuki S, Uoto K, Mitsui I, Matsumoto K, et al. Antitumor agents. 7. Synthesis and antitumor activity of novel hexacyclic camptothecin analogues. J Med Chem 1994 ; 37 : 3033-9.
26. Mitsui I, Kumazawa E, Hirota Y, Aonuma M, Sugimori M, Ohsuki S, et al. A new water-soluble camptothecin derivative, DX-8951f, exhibits potent antitumor activity against human tumors in vitro and in vivo. Jpn J Cancer Res 1995 ; 86 : 776-82.
27. Joto N, Ishii M, Minami M, Kuga H, Mitsui I, Tohgo A. DX-8951f, a water-soluble camptothecin analog, exhibits potent antitumor activity against a human lung cancer cell line and its SN-38-resistant variant. Int J Cancer 1997 ; 72 : 680-6.
28. Takiguchi S, Kumazawa E, Shimazoe T, Tohgo A, Kono A. Antitumor effect of DX-8951, a novel camptothecin analog, on human pancreatic tumor cells and their CPT-11-resistant variants cultured in vitro and xenografted into nude mice. Jpn J Cancer Res 1997 ; 88 : 760-9.
29. Lackey K, Sternbach DD, Croom DK, Emerson DL, Evans MG, Leitner PL, et al. Water soluble inhibitors of topo-isomerase I : quaternary salt derivatives of camptothecin. J Med Chem 1996 ; 39 : 713-9.
30. Xie ZF, Ootsu K, Akimoto H. Convergent approach to water soluble camptothecin derivatives. Bioorg Med Chem Lett 1995 ; 5 : 2189-94.
31. Jew SS, Kim HJ, Kim MG, Roh EY, Cho YS, Kim JK, et al. Synthesis and antitumor activity of 7-substituted 20(RS)-camptothecin analogs. Bioorg Med Chem Lett 1996 ; 6 : 845-8.
32. Uehling DE, Nanthakumar SS, Croom D, Emerson DL, Leitner PP, Luzzio MJ, et al. Synthesis, topo-isomerase I inhibitory activity, and in vivo evaluation of 11-azacamptothecin analogs. J Med Chem 1995 ; 38 : 1106-18.
33. Sugimori M, Ejima A, Ohsuki S, Matsumoto K, Kawato Y, Yasuoka M, et al. Antitumor agents. VI. Synthesis and antitumor activity of ring A-, ring B-, and ring C-modified derivatives of camptothecin. Heterocycles 1994 ; 38 : 81-94.
34. Bedeschi A, Zarini F, Cabri W, Candiani I, Penco S, Capolongo L, et al. Synthesis and antitumor activity of a new class of water soluble camptothecin derivatives. Bioorg Med Chem Lett 1996 ; 6 : 671-4.
35. Wang HK, Liu SY, Hwang KM, Taylor G, Lee KH. Synthesis of novel water-soluble 7-(aminoacylhydrazono)-formyl camptothecins with potent inhibition of DNA topo-isomerase I. Bioorg Med Chem 1994 ; 2 : 1397-402.
36. Hoki Y, Fujimori A, Pommier Y. Differential cytotoxicity of clinically important camptothecin derivatives in P-glycoprotein-overexpressing cell lines. Cancer Chemother Pharmacol 1997 ; 40 : 433-8.
37. Sugarman SM, Zou Y, Wasan K, Poirot K, Kumi R, Reddy S, et al. Lipid-complexed camptothecin : formulation and initial biodistribution and antitumor activity studies. Cancer Chemother Pharmacol 1996 ; 37 : 531-8.
38. Merisko-Liversidge E, Sarpotdar P, Bruno J, Hajj S, Wei L, Peltier N, et al. Formulation and anritumor activity evaluation of nanocrystalline suspensions of poorly soluble anticancer drugs. Pharm Res 1996 ; 13 : 272-8.
39. Shenderova A, Burke TG, Schwendeman SP. Stabilization of 10-hydroxycamptothecin in poly(lactide-co-glycolide) microsphere delivery vehicles. Pharm Res 1997 ; 14 : 1406-14.
40. Ewend MG, Williams JA, Tabassi K, Tyler BM, Babel KM, Anderson RC, et al. Local delivery of chemotherapy and concurrent external beam radiotherapy prolongs survival in metastatic brain tumor models. Cancer Res 1996 ; 56 : 5217-23.
41. Nagata H, Kaneda N, Furuta T, Sawada S, Yokokura T, Miyasaka T, et al. Action of 7-ethylcamptothecin on tumor cells and its disposition in mice. Cancer Treat Rep 1987 ; 71 : 341-8.
42. Yaegashi T, Sawada S, Nagata H, Furuta T, Yokokura T, Miyasaka T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ring-substituted 7-ethylcamptothecins and their E-ring-modified water-soluble derivatives. Chem Pharm Bull 1994 ; 42 : 2518-25.
43. Peel M, Milstead MW, Sternbach DD, Besterman JM, Leitner P, Morton B. Novel A-ring modified camptothecins as topo-isomerase I inhibitors. Bioorg Med Chem Lett 1995 ; 5 : 2129-32.
44. Josien H, Bom D, Curran DP, Zheng YH, Chou TC. 7-Silylcamptothecins (silatecans) : a new familly of camptothecin antitumor agents. Bioorg Med Chem Lett 1997 ; 7 : 3189-94.
45. Valenti M, Nieves-Neira W, Kohlhagen G, Kohn KW, Wall ME, Wani MC, et al. Novel 7-alkyl methylenedioxy-camptothecin derivatives exhibit increased cytotoxicity and induce persistent cleavable complexes both with purified mammalian topo-isomerase I and in human colon carcinoma SW620 cells. Mol Pharmacol 1997 ; 52 : 82-7.
46. Redinbo MR, Stewart L, Kuhn P, Champoux JJ, Hol WGJ. Crystal structure of human topo-isomerase I in covalent and noncovalent complexes with DNA. Science 1998 ; 279 : 1504-13.
47. Carrigan SW, Fox PC, Wall ME, Wani MC, Bowen JP. Comparative molecular field analysis and molecular modeling studies of 20-(S)-camptothecin analogs as inhibitors of DNA topo-isomerase I and anticancer/antitumor agents. J Comput Aided Mol Des 1997 ; 11 : 71-8.
48. Pommier Y, Kohlhagen G, Kohn KW, Leteurtre F, Wani MC, Wall ME. Interaction of an alkylating camptothecin derivative with a DNA base at topo-isomerase I-DNA cleavage sites. Proc Natl Acad Sci USA 1995 ; 92 : 8861-5.
49. Zhao R, Luo Guan L, Oreski B, Lown ?. Synthesis, topo-isomerase I inhibitory activity and in vitro cytotoxicity of camptothecin derivatives bearing five-membered heterocycle containing 10-substituents. Anticancer Drug Des 1998 ; 13 : 145-57.
50. Zhao R, Al-Said NH, Sternbach DL, Lown JW. Camptothecin and minor-groove binder hybrid molecules : synthesis, inhibition of topo-isomerase I, and anticancer cytotoxiciry in vitro. J Med Chem 1997 ; 40 : 216-25.
51. Sawada S, Okajima S, Aiyama R, Nokata K, Furuta T, Yokokura T, et al. Synthesis and antitumor activity of 20(S)-camptothecin derivatives : carbamate-linked, water-soluble derivatives of 7-ethyl-10-hydroxycamptothecin. Chem Pharm Bull 1991 ; 39 : 1446-50.
52. Yaegashi T, Nokata K, Sawada S, Furuta T, Yokokura T, Miyasaka T. Chemical modification of an antitumor alkaloid, 20(S)-camptothecin : glycosides, phosphates and sulfates of 7-ethyl-10-hydroxycamptothecin. Chem Pharm Bull 1992 ; 40 : 131-5.
53. Takayama H, Watanabe A, Hosokawa M, Chiba K, Satoh T, Aimi N. Synthesis of a new class of camptothecin derivatives, the longchain fatty acid esters of 10-hydroxycamptothecin, as a potent prodrug candidate, and their in vitro metabolic conversion by carboxylesterases. Bioorg Med Chem Lett 1998 ; 8 : 415-8.
54. Wall ME, Wani MC, Nicholas AW, Manikumar G, Tele C, Moore L, et al. Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs. J Med Chem 1993 ; 36 : 2689-700.
55. Greenwald RB, Pendri A, Conover C, Gilbert C, Yang R, Xia J. Drug delivery systems. 2. Camptothecin 20-O-poly(ethylene glycol) ester transport forms. J Med Chem 1996 ; 39 : 1938-40.
56. Cao Z, Harris N, Kozielski A, Vardeman D, Stehlin JS, Giovanella B. Alkyl esters of camptothecin and 9-nitrocamptothecin : synthesis, in vitro pharmacokinetics, toxicity, and antitumor activity. J Med Chem 1998 ; 41 : 31-7.
57. Adamovics JA, Hutchinson CR. Prodrug analogues of the antitumor alkaloid camptothecin. J Med Chem 1979 ; 22 : 310-4.
58. 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 : 310-3.
59. Burke TG. Chemistry of the camptothecins in the bloodstream. Drug stabilization and optimization of activity. Ann NY Acad Sci 1996 ; 803 : 29-31.
60. Hertzberg RP, Caranfa MJ, Holden KG, Jakas DR, Gallagher G, Mattern MR, et al. Modification of the hydroxy lactone ring of camptothecin : inhibition of mammalian topo-isomerase I and biological activity. J Med Chem 1989 ; 32 : 715-20.
61. Lavergne O, Lesueur-Ginot L, Pla Rhodas F, Bigg DCH. BN 80245 : an E-ring modified camptothecin with potent antiproliferative and topo-isomerase I inhibitory activities. Bioorg Med Chem Lett 1997 ; 7 : 2235-8.
62. Lavergne O, Lesueur-Ginot L, Pla Rhodas F, Kasprzyk PG, Pommier J, Demarquay D, et al. Homocamptothecins (hCPTs) : synthesis and antitumor activity of novel E-ring modified camptothecin analogs. J Med Chem 1999 ; in press.
63. Lesueur-Ginot L, Kasprzyk PG, Kiss R, Demarquay D, Lavergne O, Bigg DCH. BN-80245, an E-ring modified camptothecin, displays potent topo-isomerase-I mediated antiproliferative activity in vitro and in vivo. Amsterdam : The Eight Conference on DNA Topoisomerases in Therapy, Oct. 15-17, 1997 (abst. 13).