Homocamptothecins: Potent topoisomerase I inhibitors and promising anticancer drugs

Critical Reviews in Oncology/Hematology

Volumn 45, Issue 1, 2003, Pages 91-108

  Bailly, Christian ^a  

^a Institut de Recherche sur le Cancer de Lille   (France)

Author keywords

Anticancer drugs; Camptothecin; DNA cleavage; Homocamptothecin; Topoisomerase I

Indexed keywords

6 [2 (DIMETHYLAMINO)ETHYLAMINO] 3 HYDROXY 7H INDENO[2,1 C]QUINOLIN 7 ONE; 7 ETHYL 10 HYDROXYCAMPTOTHECIN; ACRIDINE; ANTINEOPLASTIC AGENT; BELOTECAN; BISPHENAZINE; BN 80245; BN 80765; BN 80927; BN 81652; BN 82062; BN 82154; CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; DB 90; DIFLOMOTECAN; DN 80915; DNA TOPOISOMERASE INHIBITOR; DU 1441; EXATECAN; GIMATECAN; INDENOQUINOLINE; INTOPLICINE; IRINOTECAN; LACTONE; LURTOTECAN; PHENAZINE DERIVATIVE; QUINOLINE DERIVATIVE; S 36272; TOPOTECAN; UNCLASSIFIED DRUG; XR 5000; XR 5944; DNA TOPOISOMERASE; DRUG DERIVATIVE; ENZYME INHIBITOR; HOMOCAMPTOTHECIN;

AMINO ACID SEQUENCE; ANTINEOPLASTIC ACTIVITY; CLINICAL TRIAL; COLON CARCINOMA; DNA CLEAVAGE; DRUG DESIGN; DRUG EFFECT; DRUG INHIBITION; DRUG STABILITY; ENZYME INHIBITION; HUMAN; PROSTATE CARCINOMA; REVIEW; STRUCTURE ACTIVITY RELATION; TRANSESTERIFICATION; TREATMENT OUTCOME; ANIMAL; CHEMISTRY; DRUG ANTAGONISM; DRUG RESISTANCE; LEUKEMIA;

ANIMALS; ANTINEOPLASTIC AGENTS; CAMPTOTHECIN; DNA TOPOISOMERASES, TYPE I; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; ENZYME INHIBITORS; HUMANS; LEUKEMIA;

EID: 0037212083     PISSN: 10408428     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1040-8428(02)00090-2     Document Type: Review

References (157)

1. Pommier Y. Diversity of DNA topoisomerases I and inhibitors. Biochimie. 80:1998;255-270.
2. Pommier Y., Pourquier P., Fan Y., Strumberg D. Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta. 1400:1998;83-106.
3. Pommier Y., Pourquier P., Urasaki Y., Wu J., Laco G.S. Topoisomerase I inhibitors: selectivity and cellular resistance. Drug Resist. Updates. 2:1999;307-318.
4. Yakubovskaya E.A., Gabilov A.G. Topoisomerases: mechanisms of DNA topological alterations. Mol. Biol. 33:1999;368-384.
5. Champoux J.J. DNA topoisomerases: structure, function and mechanism. Annu. Rev. Biochem. 70:2001;369-413.
6. Wang J.C. DNA topoisomerases. Annu. Rev. Biochem. 65:1996;635-691.
7. Juan C.C., Hwang J.L., Liu A.A., et al. Human DNA topoisomerase I is encoded by a single-copy gene that maps to chromosome region 20q12-13.2. Proc. Natl. Acad. Sci. USA. 85:1988;8910-8913.
8. D'Arpa P., Machlin P.S., Ratrie H. III, Rothfield N.F., Cleveland D.W., Earnshaw W.C. cDNA cloning of human DNA topoisomerase I: catalytic activity of a 67.7-kDa carboxyl-terminal fragment. Proc. Natl. Acad. Sci. USA. 85:1988;2543-2547.
9. Shuman S. Vaccinia virus DNA topoisomerase: a model eukaryotic type IB enzyme. Biochim. Biophys. Acta. 1400:1998;321-337.
10. Been M.D., Burgess R.R., Champoux J.J. Nucleotide sequence preference at rat liver and wheat germ type 1 DNA topoisomerase breakage sites in duplex SV40 DNA. Nucleic Acids Res. 12:1984;3097-3114.
11. Capranico G., Binaschi M. DNA sequence selectivity of topoisomerases and topoisomerase poisons. Biochim. Biophys. Acta. 1400:1988;185-194.
12. Thompsen B., Mollerup S., Bonven B.J., et al. Sequence specificity of DNA topoisomerase I in the presence and absence of camptothecin. EMBO J. 6:1987;1817-1823.
13. Porter S.E., Champoux J.J. Mapping in vivo topoisomerase I sites on simian virus 40 DNA: asymmetric distribution of sites on replicating molecules. Mol. Cell. Biol. 9:1989;541-550.
14. Jaxel C., Capranico G., Kerrigan D., Kohn K.W., Pommier Y. Effects of local DNA sequence on topoisomerase I cleavage in the presence or absence of camptothecin. J. Biol. Chem. 266:1991;20418-20423.
15. Tanizawa A., Kohn K.W., Pommier Y. Induction of cleavage in topoisomerase I c-DNA by topoisomerase I enzymes from calf thymus and wheat germ in the presence and absence of camptothecin. Nucleic Acids Res. 21:1993;5157-5166.
16. Stewart L., Redinbo M.R., Qiu X., Hol W.G., Champoux J.J. A model for the mechanism of human topoisomerase I. Science. 279:1998;1534-1541.
17. Yang Z., Champoux J.J. The role of histidine 632 in catalysis by human topoisomerase I. J. Biol. Chem. 276:2001;677-685.
18. Cheng C., Kussie P., Pavletich N., Shuman S. Conservation of structure and mechanism between eukaryotic topoisomerase I and site-specific recombinases. Cell. 92:1998;841-850.
19. Wittschieben J., Petersen B.O., Shuman S. Replacement of the active site tyrosine of vaccinia DNA topoisomerase by glutamate, cysteine or histidine converts the enzyme into a site-specific endonuclease. Nucleic Acids Res. 26:1998;490-496.
20. Krogh B.O., Shuman S. Catalytic mechanism of DNA topoisomerase IB. Mol. Cell. 5:2000;1035-1041.
21. Redinbo M.R., Stewart L., Kuhn P., Champoux J.J., Hol W.G.J. Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA. Science. 279:1998;1504-1513.
22. Redinbo M.R., Champoux J.J., Hol W.G.J. Novel insights into catalytic mechanism from a crystal structure of human topoisomerase I complex with DNA. Biochemistry. 39:2000;6832-6840.
23. Chillemi G., Castrignano T., Desideri A. Structure and hydration of the DNA-human topoisomerase I covalent complex. Biophys. J. 81:2001;490-500.
24. Henningfeld K.A., Arslan T., Hecht S.M. Alteration of DNA primary structure by DNA topoisomerase I, isolation of the covalent topoisomerase I-DNA binary complex in enzymatically competent form. J. Am. Chem. Soc. 118:1996;11701-11714.
25. Wall M.E., Wani M.C., Cook C.E., Palmer K.H., McPhail A.T., Sim G.A. Plant antitumor agents I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc. 88:1966;3888-3890.
26. Lu H., McKnight T.D. Tissue-specific expression of the beta-subunit of tryptophan synthase in Camptotheca acuminata, an indole alkaloid-producing plant. Plant Physiol. 120:1999;43-52.
27. Kutchan T.M. Alkaloid biosynthesis; the basis for metabolic engineering of medicinal plants. Plant Cell. 7:1995;1059-1070.
28. Lopez-Meyer M., Nessler C.L., McKnight T.D. Sites of accumulation of the antitumor alkaloid camptothecin in Camptotheca acuminata. Planta Med. 60:1994;558-560.
29. Nolte B.A., Lineberger R.D., Reed D.W., Rumpho M.F. Rapid micro-assay of camptothecin in Camptotheca acuminata. Planta Med. 67:2001;376-378.
30. Zhou B.N., Hoch J.M., Johnson R.K., et al. Use of COMPARE analysis to discover new natural product drugs: isolation of camptothecin and 9-methoxycamptothecin from a new source. J. Nat. Prod. 63:2000;1273-1276.
31. Hsiang Y.H., Hertzberg R., Hecht S., Liu L.F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J. Biol. Chem. 260:1985;14873-14878.
32. Hsiang Y.H., Liu L.F. Identification of mammalian topoisomerase I as an intracellular target of the antitumor drug camptothecin. Cancer Res. 48:1988;1722-1726.
33. Hertzberg R.P., Caranfa M.J., Hecht S.M. On the mechanism of topoisomerase I inhibition by camptothecin: evidence for binding to an enzyme-DNA complex. Biochemistry. 28:1989;4629-4638.
34. Kjeldsen E., Svejstrup J.Q., Gromova H., Alsner J., Westergaard O. Camptothecin inhibits both the cleavage and religation reactions of eukaryotic DNA topoisomerase I. J. Mol. Biol. 228:1992;1025-1030.
35. Masuda N., Kudoh S., Fukuoka M. Irinotecan (CPT-11): pharmacology and clinical applications. Crit. Rev. Oncol. Hematol. 24:1996;3-26.
36. Stewart C.F. Topoisomerase I interactive agents. Cancer Chemother. Biol. Res. Modif. 19:2001;85-128.
37. Kehrer D.F.S., Soepenberg O., Loos W.J., Verweij J., Sparreboom A. Modulation of camptothecin analogs in the treatment of cancer: a review. Anti-Cancer Drugs. 12:2001;89-105.
38. Eckhardt S.G., Baker S.D., Eckardt J.R., et al. Phase I and pharmacokinetic study of GI147211, a water-soluble camptothecin analogue, administered for 5 consecutive days every 3 weeks. Clin. Cancer Res. 4:1998;595-604.
39. Gamucci T., Paridaens R., Hemrich B., et al. Activity and toxicity of GI147211 in breast, colorectal and non-small-cell lung cancer patients: an EORTC-ECSG phase II clinical study. Ann. Oncol. 11:2000;793-797.
40. De Jager R., Cheverton P., Tamanoi K., et al. DX-8951 f: summary of phase I clinical trials. Ann. New York Acad. Sci. 922:2000;260-273.
41. Royce M.E., Hoff P.M., Dumas P., et al. Phase I and pharmacokinetic study of exatecan mesylate (DX-8951f): a novel camptothecin analog. J. Clin. Oncol. 19:2001;1493-1500.
42. Minami H., Fujii H., Igarashi T., et al. Phase I and pharmacological study of a new camptothecin derivative, exatecan mesylate (dx-8951 f), infused over 30 min every 3 weeks. Clin. Cancer Res. 7:2001;3056-3064.
43. Thomas R.R., Dahut W., Harold N., et al. A phase I and pharmacologic study of 9-aminocamptothecin administered as a 120-h infusion weekly to adult cancer patients. Cancer Chemother. Pharmacol. 48:2001;215-222.
44. Argiris A., Heald P., Kuzel T., et al. Phase II trial of 9-aminocamptothecin as a 72-h infusion in cutaneous T-cell lymphoma. Invest. New Drugs. 19:2002;321-326.
45. Vokes E.E., Gordon G.S., Rudin C.M., et al. A phase II trial of 9-aminocaptothecin (9-AC) as a 120-h infusion in patients with non-small cell lung cancer. Invest. New Drugs. 19:2002;329-333.
46. Giovanella B.C., Stehlin J.S., Hinz H.R., Kozielski A.J., Harris N.J., Vardeman D.M. Preclinical evaluation of the anticancer activity and toxicity of 9-nitro-20(S)-camptothecin (Rubitecan). Int. J. Oncol. 20:2002;81-88.
47. Konstadoulakis M.M., Antonakis P., Tsibloutis B.G., et al. A phase II study of 9-nitrocamptothecin in patients with advanced pancreatic adenocarcinoma. Cancer Chemother. Pharmacol. 48:2001;417-420.
48. Kohara H., Tabata M., Kiura K., et al. Synergistic effects of topoisomerase I inhibitor, 7-ethyl-10-hydroxycamptothecin, and irradiation in a cisplatin-resistant human small cell lung cancer cell line. Clin. Cancer Res. 8:2002;287-292.
49. Long B.H., Balasubramanian B.N. Non-camptothecin topoisomerase I compounds as potential anticancer agents. Exp. Opin. Ther. Pat. 10:2000;635-666.
50. Lopez-Lazaro M., Martin-Cordero C., Ayuso M.J. Two new flavonol glycosides as DNA topoisomerase I poisons. Z. Naturforsch. 55:2000;898-902.
51. Zhou B.N., Johnson R.K., Mattern M.R., et al. Isolation and biochemical characterization of a new topoisomerase I inhibitor from Ocotea leucoxylon. J. Nat. Prod. 63:2000;17-221.
52. Kanai Y., Ishiyama D., Senda H., et al. Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. I. Producing strain, fermentation, isolation, physico-chemical properties and biological activity. J. Antibiot. 53:2000;863-872.
53. Lin C.F., Hsieh P.C., Lu W.D., Chiu H.F., Wu M.J. A series of enediynes as novel inhibitors of topoisomerase I. Bioorg. Med. Chem. 9:2001;1707-1711.
54. Lynch M.A., Duval O., Sukhanova A., et al. Synthesis biological activity and comparative analysis of DNA binding affinities and human DNA topoisomerase I inhibitory activities of novel 12-alkoxy-benzo[c]phenanthridinium salts. Bioorg. Med. Chem. Lett. 11:2001;2643-2646.
55. Zhao L., Kim T.S., Ahn S., et al. Synthesis, topoisomerase I inhibition and antitumor cytotoxicity of 2,2′:6r,2n-, 2,2′:6′,3″- and 2,2′:6′,4-terpyridine derivatives. Bioorg. Med. Chem. Lett. 11:2001;2659-2662.
56. Suzuki K., Yahara S., Maehata K., Uyeda M. Isoaurostatin, a novel topoisomerase inhibitor produced by Thermomonospara alba. J. Nat. Prod. 64:2001;204-207.
57. Mekapati S.B., Hansch C. Comparative QSAR studies on bibenzimidazoles and terbenzimidazoles inhibiting topoisomerase I. Bioorg. Med. Chem. 9:2001;2885-2893.
58. Bailly C. Topoisomerase I poisons and suppressors as anticancer drugs. Curr. Med. Chem. 7:2000;39-58.
59. Hecht S.M., Berry D.E., MacKenzie L., Busby R.W., Nasuti C.A. A strategy for identifying novel, mechanistically unique inhibitors of topoisomerase I. J. Nat. Prod. 55:1992;401-413.
60. Laco G.S., Collins J.R., Luke B.T., et al. Human topoisomerase I inhibition: docking camptothecin and derivatives into a structure-based active site model. Biochemistry. 41:2002;1428-1435.
61. Fan Y., Weinstein J.N., Kohn K.W., Shi L.M., Pommier Y. Molecular modeling studies of the DNA-topoisomerase I ternary cleavable complex with camptothecin. J. Med. Chem. 41:1998;22l6-2226.
62. Kerrigan J.E., Pilch D.S. A structural model for the ternary cleavable complex formed between human topoisomerase I, DNA and camptothecin. Biochemistry. 40:2001;9792-9798.
63. Arimondo P.R., Hélèene C. Design of new anti-cancer agents based on topoisomerase poisons targeted to specific DNA sequences. Curr. Med. Chem. Anti-Cancer Agents. 1:2001;219-235.
64. Matteuci M., Lin K.Y., Huang T., et al. Sequence-specific targeting of duplex DNA using a camptothecin-triple helix forming oligonucleotide conjugate and topoisomerase I. J. Am. Chem. Soc. 119:1997;6939-6940.
65. Arimondo P.B., Bailly C., Boutorine A., Sun J.S., Garestier T., Hélène C. Targeting topoisomerase I cleavage to specific sequences of DNA by triple helix-forming oligonucleotide conjugates. A comparison between a rebeccarnycin derivative and camptothecin. CR Acad. Sci. III. 322:1999;785-790.
66. Arimondo P.B., Boutorine A., Baldeyrou B., et al. Design and optimization of camptothecin conjugates of triple helix-forming oligonucleotides for sequence-specific DNA cleavage by topoisomerase I. J. Biol. Chem. 277:2001;3132-3140.
67. Arimondo P., Bailly C., Boutorine A., et al. Directing topoisomerase I mediated DNA cleavage to specific sites by camptothecin tethered to minor- and major-groove ligands. Angew. Chem. Int. Ed. 40:2001;3045-3048.
68. Wang C.C., Dervan P.B. Sequence-specific trapping of topoisomerase I by DNA binding polyamide-camptothecin conjugates. J. Am. Chem. Soc. 123:2001;8657-8661.
69. Pommier Y., Kohlhagen G., Pourquier P., Sayer J.M., Kroth H., Jerina D.M. Position-specific trapping of topoisomerase I-DNA cleavage complexes by intercalated benzo[a]-pyrene diol epoxide adducts at the 6-amino group of adenine. Proc. Natl. Acad. Sci. USA. 97:2000;10739-10744.
70. Burke T.G., Mi Z. Preferential binding of the carboxylate form of camptothecin by human serum albumin. Anal. Biochem. 212:1993;285-287.
71. Mi Z., Burke T.G. Differential interactions of camptothecin lactone and carboxylate forms with human blood components. Biochemistry. 33:1994;10325-10336.
72. Burke T.G., Bom D. Camptothecin design and delivery approaches for elevating anti-topoisomerase I activities in vivo. Ann. New York Acad. Sci. 922:2000;36-45.
73. Burke T.G., Mi Z. Ethyl substitution at the 7 position extends the hall-life of 10-hydroxycamptothecin in the presence of human serum albumin. J. Med. Chem. 36:1993;2580-2582.
74. Burke T.G., Mi Z. The structural basis of camptothecin interactions with human serum albumin: impact on drug stability. J. Med. Chem. 37:1994;40-46.
75. Josien H., Bom D., Curran D.P., Zheng Y.H., Chou T.C. 7-Silylcamptothecins (silatecans): a new family of camtothecin antitumor agents. Bioorg. Med. Chem. Lett. 7:1997;3189-3194.
76. Dallavalle S., Ferrari A., Biasotti B., et al. Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity. J. Med. Chem. 44:2001;3264-3274.
77. Tanizawa A., Fujimori A., Fujimori Y., Pommier Y. Comparison of topoisomerase I inhibition, DNA damage, and cytotoxicity of camptothecin derivatives presently in clinical trials. J. Natl. Cancer Inst. 86:1994;836-842.
78. Mi Z., Malak H., Burke T.G. Reduced albumin binding promotes the stability and activity of topotecan in human blood. Biochemistry. 34:1995;13722-13728.
79. Yao S., Murali D., Seetharamulu P., et al. Topotecan lactone selectively binds to double- and single-stranded DNA in the absence of topoisomerase I. Cancer Res. 58:1998;3782-3786.
80. Yang D., Strode J.T., Spielman H.P., Wang A.H.J., Burke T.G. DNA interaction of two clinical camptothecin drugs stabilize their active lactone forms. J. Am. Chem. Soc. 120:1998;2979-2980.
81. Bom D., Curran D.P., Kruszewski S., et al. The novel silatecan 7-tert-butyldimethylsilyl-l0-hydroxycamptothecin displays high lipophilicity, improved human blood stability, and potent anticancer activity. J. Med. Chem. 43:2000;3970-3980.
82. Bom D., Curran D.P., Zhang J., et al. The highly lipophilic DNA topoisomerase I inhibitor DB-67 displays elevated lactone levels in human blood and potent anticancer activity. J. Control. Release. 74:2001;325-333.
83. Pollack I.F., Erff M., Bom D., Burke T.G., Strode J.T., Curran D.P. Potent topoisomerase I inhibition by novel silatecans eliminates glioma proliferation in vitro and in vivo. Cancer Res. 59:1999;4898-4905.
84. Hare C.B., Elion G.B., Houghton P.J., et al. Therapeutic efficacy of the topoisomerase I inhibitor 7-ethyl-10-(4-[1-piperidino]-1-piperidino)-carbonyloxy-camptothecin against pediatric and adult central nervous system tumor xenografts. Cancer Chemother. Pharmacol. 39:1997;187-191.
85. Keir S.T., Hausheer F., Lawless A.A., Bigner D.D., Friedman H.S. Therapeutic activity of 7-[(2-trimethylsilyl)ethyl)]-20-(S)-camptothecin against central nervous system tumor-derived xenografts in athymic mice. Cancer Chemother. Pharmacol. 48:2001;83-87.
86. Yin M.B., Guo B., Vanhoefer U., et al. Characterization of protein kinase chk1 essential for the cell cycle checkpoint after exposure of human head and neck carcinoma A253 cells to a novel topoisomerase I inhibitor BNP1350. Mol. Pharmacol. 57:2000;453-459.
87. Matsui S., Endo W., Wrzosek C., et al. Characterisation of a synergistic interaction between a thymidylate synthase inhibitor, ZD1694, and a novel lipophilic topoisomerase I inhibitor karenitecin, BNP1100: mechanisms and clinical implications. Eur. J. Cancer. 35:1999;984-993.
88. Lee J.H., Lee J.M., Kim J.K., et al. Antitumor activity of 7-[2-(N-isopropylamino)ethyl]-(20S)-camptothecinf CKD602, as a potent DNA topoisomerase I inhibitor. Arch. Pharm. Res. 21:1998;581-590.
89. Lee J.H., Lee J.M., Lim K.H., et al. Preclinical and phase 1 clinical studies with Ckd-602, a novel camptothecin derivative. Ann. New York Acad. Sci. 922:2000;324-325.
90. De Cesare M., Pratesi G., Perego P., et al. Potent antitumor activity and improved pharmacological profile of ST1481, a novel 7-substituted camptothecin. Cancer Res. 61:2001;7189-7195.
91. Kim D.K., Ryu D.H., Lee J.Y., et al. Synthesis and biological evaluation of novel A-ring modified hexacyclic camptothecin analogues. J. Med. Chem. 44:2001;1594-1602.
92. Fan Y., Shi L.M., Kohn K.W., Pommier Y., Weinstein J.N. Quantitative structure-antitumor activity relationships of camptothecin analogues: cluster analysis and genetic algorithm-based studies. J. Med. Chem. 44:2001;3254-3263.
93. Hertzberg R.P., Caranfa M.J., Holden K.G., et al. Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity. J. Med. Chem. 32:1989;715-720.
94. Yaegashi T., Sawada S., Furuta T., Yokokura T., Yamaguchi K., Miyasaka T. Chemical modification of antitumor alkaloids, 20(S)-camptothecin and 7-ethylcamptothecin: reaction of the E-lactone ring portion with hydrazine hydrate. Chem. Pharm. Bull. (Tokyo). 41:1993;971-974.
95. Hsiang Y.H., Liu L.F., Wall M.E., et al. DNA topoisomerase I-mediated DNA cleavage and cytotoxicity of camptothecin analogues. Cancer Res. 49:1989;4385-4389.
96. 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: evidence for a specific receptor site and a relation to antitumor activity. Cancer Res. 49:1989;1465-1469.
97. Govindachari T.R., Ravindranath K.R., Viswanathan N. Mappicine, a minor alkaloid from Mappia Foetida Miers. J. Chem. Soc. Perkin Trans. 1:1974;1215-1217.
98. Nicholas A.W., Wani M.C., Manikumar G., Wall M.E., Kohn K.W., Pommier Y. Plant antitumor agents. 29, Synthesis and biological activity of ring D and ring E modified analogues of camptothecin. J. Med. Chem. 33:1990;972-978.
99. Ejima A., Terasawa H., Sugimori M., et al. Synthesis and antileukemic activity of (±)-20-deoxyaminocamptothecin analogues. Chem. Pharm. Bull. (Tokyo). 37:1989;2253-2255.
100. Ejima A., Terasawa H., Sugimori M., et al. Antitumor agents. V. Synthesis and antileukemic activity of E-ring-modified (RS)-camptothecin analogues. Chem. Pharm. Bull. (Tokyo). 40:1992;683-688.
101. 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. (Tokyo). 41:1993;310-313.
102. Wall M.E., Wani M.C., Nicholas A.W., et al. Plant antitumor agents, 30, synthesis and structure activity of novel camptothecin analogs. J. Med. Chem. 36:1993;2689-2700.
103. Snyder L., Shen W., Bornmann W.G., Danishefsky S.J. Synthesis of 18-nonanhydrocamptothecin analogs which retain topoisomerase I inhibitory function. J. Org. Chem. 59:1994;7033.
104. Lavergne O., Demarquay D., Kasprzyk P.G., Bigg D.C.H. Homocamptothecins; E-ring modified CPT analogues. Ann. New York Acad. Sci. 922:2000;100-111.
105. Lavergne O., Lesueur-Ginot L., Pla Rodas F., Bigg D.C.H. BN80245: an E-ring modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities. Bioorg. Med. Chem. 7:1997;2235-2238.
106. Du W., Curran D.P., Bevins R.L., Zimmer S.G., Zhang J., Burke T.G. Synthesis and evaluation of a novel E-ring modified alpha-hydroxy keto ether analogue of camptothecin. Bioorg. Med. Chem. 10:2002;103-110.
107. Lavielle G, Hautefaye P, Pierré A, et al. Camptothecin Analogues, Processes for their Preparation and Pharmaceutical Compositions Containing Them. EP 1101765 A2, ADIR ET CO, 2001.
108. Lavergne O., Lesueur-Ginot L., Pla Rodas F., et al. Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogues. J. Med. Chem. 41:1998;5410-5419.
109. Lyle R.E., Bristol J.A., Kane J.K., Portlock D.E. The synthesis of an analog of camptothecin by a general method. J. Org. Chem. 38:1973;3268-3271.
110. Comins D.L., Baevsky M.F., Hong H. A 10-step, asymmetric synthesis of (S)-camptothecin. J. Am. Chem. Soc. 114:1992;10971-10972.
111. Lesueur-Ginot L., Demarquay D., Kiss R., et al. Homocamptothecin, an E-ring modified camptothecin with enhanced lactone stability, retains topoisomerase I-targeted activity and antitumor properties. Cancer Res. 59:1999;2939-2943.
112. Chourpa I., Riou J.F., Millot J.M., Pommier Y., Manfait M. Modulation in kinetics of lactone ring hydrolysis of camptothecins upon interaction with topoisomerase I cleavage sites on DNA. Biochemistry. 37:1998;7284-7291.
113. Chauvier D., Chourpa I., Bigg D.C.H., Manfait M. Kinetics of in vitro hydrolysis of homocamptothecins as measured by fluorescence. Ann. New York Acad. Sci. 922:2000;314-316.
114. Burke T.G., Mi Z., Jiang Y., Munshi C.B. The important role of albumin in determining the relative human blood stabilities of the camptothecin anticancer drugs. J. Pharm. Sci. 84:1995;518-519.
115. Mi Z., Burke T.G. Marked interspecies variations concerning the interactions of camptothecin with serum albumins: a frequency-domain fluorescence spectroscopic study. Biochemistry. 33:1994;12540-12545.
116. Born D., Curran D.P., Chavan A.J., et al. Novel A, B, E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities. J. Med. Chem. 42:1999;3018-3022.
117. Wang X., Short G.F., Kingsbury W.D., Johnson R.K., Hecht S.M. Effects of camptothecin analogues on DNA transformations mediated by calf thymus and human DNA topoisomerase I. Chem. Res. Toxicol. 11:1998;1352-1360.
118. Wang X., Wang L.K., Kingsbury W.D., Johnson R.K., Hecht S.M. Differential effects of camptothecin analogues on topoisomerase I-mediated DNA structure modifications. Biochemistry. 37:1998;9399-9408.
119. Urasaki Y., Laco G.S., Pourquier P., et al. Characterization of a novel topoisomerase I mutation from a camptothecin-resistant human prostate cancer cell line. Cancer Res. 61:2001;1964-1969.
120. Wang X., Zhou X., Hecht S.M. Role of the 20-hydroxyl group in camptothecin binding by the topoisomerase I-DNA binary complex. Biochemistry. 38:1999;4374-4381.
121. Bailly C., Lansiaux A., Dassonneville L., et al. Homocamptothecin, an E-ring modified camptothecin analog, generates new topoisomerase I-mediated DNA breaks. Biochemistry. 38:1999;15556-15563.
122. Bailly C., Laine W., Baldeyrou B., et al. A novel B-ring modified homocamptothecin, 12-Cl-hCPT, showing antiproliferative and topoisomerase I inhibitory activities superior to SN-38. Anti-Cancer Drug Des. 16:2001;27-36.
123. Demarquay D., Huchet M., Coulomb H., et al. The homocamptothecin BN809l5 is a highly potent orally active topoisomerase I poison. Anticancer Drugs. 12:2001;9-19.
124. Pilch B., Allemand E., Facompré M., et al. Specific inhibition of SR splicing factors phosphorylation, spliceosome assembly and splicing by the anti-tumor drug NB506. Cancer Res. 61:2001;6876-6884.
125. Urasaki Y., Takebayashi Y., Pommier Y. Activity of a novel camptothecin analogue, homocamptothecin, in camptothecin-resistant cell lines with topoisomerase I alterations. Cancer Res. 60:2000;6577-6580.
126. Lavergne O., Demarquay D., Bailly C., et al. Preparation and in vitro activity of enantiomerically pure, fluorinated homocamptothecins as potent topoisomerase I poisons. J. Med. Chem. 43:2000;2285-2289.
127. Chauvier D., Morjani H., Manfait M. Homocamptothecin-daunorubicin association overcomes multidrug-resistance in breast cancer MCF7 cells. Breast Cancer Res Treat. 73:2002;113-125.
128. Larsen A., Gilbert C., Chyzak G., et al. Unusual potency of BN80915, a novel fluorinated E-ring modified camptothecin, towards human colon carcinoma cells. Cancer Res. 61:2001;2961-2967.
129. Pourquier P., Pommier Y. Topoisomerase I-mediated DNA damage. Adv. Cancer Res. 80:2001;189-216.
130. Kohn K.W., Andoh T. Symposium: downstream from topoisomerase-DNA lesions: life-or-death consequences for the cell. Cell Biochem. Biophys. 33:2000;171-173.
131. Andoh T. Signal transduction pathways leading to cell cycle arrest and apoptosis induced by DNA topoisomerase poisons. Cell Biochem. Biophys. 33:2000;181-188.
132. Kohn K.W., Shao R.G., Pommier Y. How do drug-induced topoisomerase I-DNA lesions signal to the molecular interaction network that regulates cell cycle checkpoints, DNA replication, and DNA repair. Cell Biochem. Biophys. 33:2000;175-180.
133. Li T.K., Liu L.F. Tumor cell death induced by topoisomerase-targeting drugs. Annu. Rev. Pharmacol. Toxicol. 41:2001;53-77.
134. 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. 49:1989;5077-5082.
135. Tsao Y.P., Russo A., Nyamuswa G., Silber R., Liu L.F. Interaction between replication forks and topoisomerase I-DNA cleavable complexes: studies in a cell-free SV40 DNA replication system. Cancer Res. 53:1993;5908-5914.
136. Wu J., Liu L.F. Processing of topoisomerase I cleavable complexes into DNA damage by transcription. Nucleic Acid Res. 25:1997;4181-4186.
137. Liu L.F., Desai S.D., Li T.K., Mao Y., Sun M., Sim S.P. Mechanism of action of camptothecin. Ann. New York Acad. Sci. 922:2000;1-10.
138. Collins I., Weber A., Levens D. Transcriptional consequences of topoisomerase inhibition. Mol. Cell. Biol. 21:2001;8437-8451.
139. Lansiaux A., Facompré M., Wattez N., et al. Apoptosis induced by the homocamptothecin anticancer drug BN80915 in HL-60 cells. Mol. Pharmacol. 60:2001;450-461.
140. Chauvier D., Morjani H., Manfait M. Ceramide involvement in homocamptothecin- and camptothecin-induced cytotoxicity and apoptosis in colon HT29 cells. Int. J. Oncol. 20:2002;855-863.
141. Philippart P., Harper L., Chaboteaux C., et al. Homocamptothecin, an E-ring-modified camptothecin, exerts more potent antiproliferative activity than other topoisomerase I inhibitors in human colon cancers obtained from surgery and maintained in vitro under histotypical culture conditions. Clin. Cancer Res. 6:2000;1557-1562.
142. Giovanella B.C., Stehlin J.S., Wall M.E., et al. DNA topoisomerase I-targeted chemotherapy of human colon cancer in xenografts. Science. 246:1989;1046-1048.
143. Bronstein I.B., Vorobyev S., Timofeev A., Jolles C.J., Alder S.L., Holden J.A. Elevations of DNA topoisomerase I catalytic activity and immunoprotein in human malignancies. Oncol. Res. 8:1996;17-25.
144. Chen B.M., Chen J.Y., Kao M., Lin J.B., Yu M.H., Roffler S.R. Elevated topoisomerase I activity in cervical cancer as a target for chemoradiation therapy. Gynecol. Oncol. 79:2000;272-280.
145. Jansen W.J.M., Kolfschoten G.M., Erkelens C.A.M., van Ark-Otte J., Pinedo H.M., Boven E. Anti-tumor activity of CPT-11 in experimental human ovarian cancer and human soft-tissue sarcoma. Int. J. Cancer. 73:1997;891-896.
146. van Ark-Otte J., Kedde M.A., van der Vijgh W.J.F., et al. Determinants of CPT-11 and SN-38 activities in human lung cancer cells. Br. J. Cancer. 77:1998;2171-2176.
147. Ulukan H., Muller M.T., Swaan P.W. Downregulation of topoisomerase I in differentiating human intestinal epithelial cells. Int. J. Cancer. 94:2001;200-207.
148. Lansiaux A., Bras-Goncalves R., Rosty C., Laurent-Puig P., Poupon M.F., Bailly C. Topoisomerase I-DNA covalent complexes in human colorectal cancer xenografts with different p53 and micro satellite instability status: relation with their sensitivity to CPT-11. Anticancer Res. 21:2001;471-476.
149. Bonneterre J, Cottu P, Adenis A, et al. Phase I trial of BN80915 administered intravenously in patients with advanced malignant tumours, Proc Am Assoc Cancer Res, 2000; A#234.
150. Riou J.F., Fossé P., Nguyen C.H., et al. Intoplicine (RP 60475) and its derivatives, a new class of antitumor agents inhibiting both topoisomerase I and II activities. Cancer Res. 53:1993;5987-5993.
151. Poddevin B., Riou J.F., Lavelle F., Pommier Y. Dual topoisomerase I and II inhibition by intoplicine (RP-60475), a new antitumor agent in early clinical trials. Mol. Pharmacol. 44:1993;767-774.
152. Utsugi T., Aoyagi K., Asao T., et al. Antitumor activity of a novel quinoline derivative, TAS-103, with inhibitory effects on topoisomerases I and II. Jpn. J. Cancer Res. 88:1997;992-1002.
153. Fortune J.M., Velea L., Graves D.E., Utsugi T., Yamada Y., Osheroff N. DNA topoisomerases as targets for the anticancer drug TAS-103: DNA interactions and topoisomerase catalytic inhibition. Biochemistry. 38:1999;15580-15586.
154. Stewart A.J., Mistry P., Dangerfield W., et al. Antitumor activity of XR5944, a novel and potent topoisomerase poison. Anticancer Drugs. 12:2001;359-365.
155. Caponigro F., Dittrich C., Sorensen J.B., et al. Phase II study of XR 5000, an inhibitor of topoisomerases I and II, in advanced colorectal cancer. Eur. J. Cancer. 38:2002;70-74.
156. Lavergne O., Harnelt J., Rolland A., et al. BN 80927: a novel homocamptothecin with inhibitory activities on both topoisomerase I and II. Bioorg. Med. Chem. Lett. 9:1999;2599-2602.
157. Huchet M., Demarquay D., Coulomb H., et al. The dual topoisomerase I inhibitor, BN80927, is highly potent against cell proliferation and tumor growth. Ann. New York Acad. Sci. 922:2000;303-305.