Evolution in medicinal chemistry of E-ring-modified Camptothecin analogs as anticancer agents

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 746-757

  Huang, Qingqing ^a   Wang, Lei ^a   Lu, Wei ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Anticancer drugs; Camptothecin analogs; E Ring modified; Stability

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; CAMPTOTHECIN DERIVATIVE; DIFLOMOTECAN; DNA TOPOISOMERASE; IRINOTECAN; LACTAM DERIVATIVE; LACTONE; LUOTONIN A; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CANCER CELL CULTURE; CANCER INHIBITION; CYTOTOXICITY; DRUG POTENCY; HUMAN; NONHUMAN; PROTEIN EXPRESSION; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 84875964231     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.01.058     Document Type: Short Survey

References (133)

1. M.E. Wall, M.C. Wani, C.E. Cook, K.H. Palmer, A.T. McPhail, and G.A. Sim 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
2. J.A. Gottlieb, and J.K. Luce Treatment of malignant melanoma with camptothecin (NSC-100880) Cancer Chemother. Rep. 56 1972 103 105
3. C.G. Moertel, A.J. Schutt, R.J. Reitemeier, and R.G. Hahn Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer Cancer Chemother. Rep. 56 1972 95 101
4. F.M. Muggia, P.J. Creaven, H.H. Hansen, M.H. Cohen, and O.S. Selawry Phase I clinical trial of weekly and daily treatment with camptothecin (NSC-100880): correlation with preclinical studies Cancer Chemother. Rep. 56 1972 515 521
5. Y.H. Hsiang, R. Hertzberg, S. Hecht, and L.F. Liu Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I J. Biol. Chem. 260 1985 14873 14878
6. J. Nitiss, and J.C. Wang DNA topoisomerase-targeting antitumor drugs can be studied in yeast Proc. Natl. Acad. Sci. USA 85 1988 7501 7505
7. J.J. Champoux DNA topoisomerases: structure, function, and mechanism Annu. Rev. Biochem. 70 2001 369 413
8. J.C. Wang Cellular roles of DNA topoisomerases: a molecular perspective Nat. Rev. Mol. Cell. Biol. 3 2002 430 440
9. J.C. Wang DNA topoisomerases Annu. Rev. Biochem. 65 1996 635 692
10. B.L. Staker, M.D. Feese, M. Cushman, Y. Pommier, D. Zembower, L. Stewart, and A.B. Burgin Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex J. Med. Chem. 48 2005 2336 2345
11. B.L. Staker, K. Hjerrild, M.D. Feese, C.A. Behnke, A.B. Burgin Jr., and L. Stewart The mechanism of topoisomerase I poisoning by a camptothecin analog Proc. Natl. Acad. Sci. USA 99 2002 15387 15392
12. M.R. Redinbo, L. Stewart, P. Kuhn, J.J. Champoux, and W.G. Hol Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA Science 279 1998 1504 1513
13. Y. Pommier, P. Pourquier, Y. Urasaki, J. Wu, and G.S. Laco Topoisomerase I inhibitors: selectivity and cellular resistance Drug Resist. Updat. 2 1999 307 318
14. M.C. Wani, P.E. Ronman, J.T. Lindley, and M.E. Wall Plant antitumor agents. 18. Synthesis and biological activity of camptothecin analogues J. Med. Chem. 23 1980 554 560
15. E. Fattorusso, and O. Taglialatela-Scafati Modern Alkaloids: Structure, Isolation, Synthesis and Biology 2007 Wiley-VCH
16. Y. Fan, J.N. Weinstein, K.W. Kohn, L.M. Shi, and Y. Pommier Molecular modeling studies of the DNA-topoisomerase I ternary cleavable complex with camptothecin J. Med. Chem. 41 1998 2216 2226
17. J.E. Kerrigan, and D.S. Pilch A structural model for the ternary cleavable complex formed between human topoisomerase I, DNA, and camptothecin Biochemistry 40 2001 9792 9798
18. C. Jaxel, K.W. Kohn, M.C. Wani, M.E. Wall, and Y. Pommier 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
19. C.H. Choi, Y.Y. Lee, T.J. Song, H.S. Park, M.K. Kim, T.J. Kim, J.W. Lee, J.H. Lee, D.S. Bae, and B.G. Kim Phase II study of belotecan, a camptothecin analogue, in combination with carboplatin for the treatment of recurrent ovarian cancer Cancer 117 2011 2104 2111
20. J. Hong, M. Jung, Y.J. Kim, S.J. Sym, S.Y. Kyung, J. Park, S.P. Lee, J.W. Park, E.K. Cho, S.H. Jeong, D.B. Shin, and J.H. Lee Phase II study of combined belotecan and cisplatin as first-line chemotherapy in patients with extensive disease of small cell lung cancer Cancer Chemother. Pharmacol. 69 2012 215 220
21. R. Garcia-Carbonero, and J.G. Supko Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins Clin. Cancer Res. 8 2002 641 661
22. J.F. Pizzolato, and L.B. Saltz The camptothecins Lancet 361 2003 2235 2242
23. S. Dallavalle, A. Ferrari, B. Biasotti, L. Merlini, S. Penco, G. Gallo, M. Marzi, M.O. Tinti, R. Martinelli, C. Pisano, P. Carminati, N. Carenini, G. Beretta, P. Perego, M. De Cesare, G. Pratesi, and F. Zunino Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity J. Med. Chem. 44 2001 3264 3274
24. D. Hess, S. Boehm, A. Delmonte, E. Gallerani, P. Barbieri, S. Pace, P. Carminati, S. Marsoni, N. Coceani, and C. Sessa Clinical development of namitecan (ST1968), a novel camptothecin derivative with high antitumor activity: phase I clinical data J. Clin. Oncol. 27 2009 suppl; abstr 2570
25. A. Fasolo, G. Del Conte, R.G. Calderone, E. Gallerani, N. Hagner, P. Barbieri, L. Luraghi, S. Pace, F. Capocasa, N. Coceani, E. Maccioni, D. Hess, C. Sessa, and L. Gianni Phase I clinical trial of namitecan (ST1968): results with D1-3 q3wks schedule J. Clin. Oncol. 29 2011 (suppl; abstr e13570)
26. P.N. Munster, and A.I. Daud Preclinical and clinical activity of the topoisomerase I inhibitor, karenitecin, in melanoma Expert Opin. Investig. Drugs 20 2011 1565 1574
27. D. Bom, D.P. Curran, S. Kruszewski, S.G. Zimmer, J. Thompson Strode, G. Kohlhagen, W. Du, A.J. Chavan, K.A. Fraley, A.L. Bingcang, L.J. Latus, Y. Pommier, and T.G. Burke The novel silatecan 7-tert-butyldimethylsilyl-10- hydroxycamptothecin displays high lipophilicity, improved human blood stability, and potent anticancer activity J. Med. Chem. 43 2000 3970 3980
28. N. Joto, M. Ishii, M. Minami, H. Kuga, I. Mitsui, and A. Tohgo 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 72 1997 680 686
29. O. Lavergne, L. Lesueur-Ginot, F. Pla Rodas, P.G. Kasprzyk, J. Pommier, D. Demarquay, G. Prevost, G. Ulibarri, A. Rolland, A.M. Schiano-Liberatore, J. Harnett, D. Pons, J. Camara, and D.C. Bigg Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogues J. Med. Chem. 41 1998 5410 5419
30. G.M. Cragg, and D.J. Newman A tale of two tumor targets: topoisomerase I and tubulin. The Wall and Wani contribution to cancer chemotherapy J. Nat. Prod. 67 2004 232 244
31. F. Zunino, and G. Pratesi Camptothecins in clinical development Expert Opin. Investig. Drugs 13 2004 269 284
32. C.J. Thomas, N.J. Rahier, and S.M. Hecht Camptothecin: current perspectives Bioorg. Med. Chem. 12 2004 1585 1604
33. T.R. Govindachari, K.R. Ravindranath, and N. Viswanathan Mappicine, a minor alkaloid from Mappia foetida Miers J. Chem. Soc. Perkin. 1 11 1974 1215 1217
34. R.P. Hertzberg, M.J. Caranfa, K.G. Holden, D.R. Jakas, G. Gallagher, M.R. Mattern, S.M. Mong, J.O. Bartus, R.K. Johnson, and W.D. Kingsbury Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity J. Med. Chem. 32 1989 715 720
35. S. Sawada, T. Yaegashi, T. Furuta, T. Yokokura, and T. Miyasaka Chemical modification of an antitumor alkaloid, 20(S)-camptothecin: E-lactone ring-modified water-soluble derivatives of 7-ethylcamptothecin Chem. Pharm. Bull. 41 1993 310 313
36. T. Yaegashi, S. Sawada, T. Furuta, T. Yokokura, K. Yamaguchi, and T. Miyasaka Chemical modification of antitumor alkaloids, 20(S)-camptothecin and 7-ethylcamptothecin: reaction of the E-lactone ring portion with hydrazine hydrate Chem. Pharm. Bull. 41 1993 971 974
37. J.A. Adamovics, and C.R. Hutchinson Prodrug analogues of the antitumor alkaloid camptothecin J. Med. Chem. 22 1979 310 314
38. A.W. Nicholas, M.C. Wani, G. Manikumar, M.E. Wall, K.W. Kohn, and Y. Pommier 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
39. A. Ejima, H. Terasawa, M. Sugimori, S. Ohsuki, K. Matsumoto, Y. Kawato, M. Yasuoka, and H. Tagawa Antitumor agents. V. Synthesis and antileukemic activity of E-ring-modified (RS)-camptothecin analogues Chem. Pharm. Bull. (Tokyo) 40 1992 683 688
40. A. Ejima, H. Terasawa, M. Sugimori, S. Ohsuki, K. Matsumoto, Y. Kawato, and H. Tagawa Synthesis and antileukemic activity of (+-)-20- deoxyaminocamptothecin analogues Chem. Pharm. Bull. (Tokyo) 37 1989 2253 2255
41. L. Snyder, W. Shen, W.G. Bornmann, and S.J. Danishefsky Synthesis of 18-noranhydrocamptothecin analogs which retain topoisomerase I inhibitory function J. Org. Chem. 59 1994 7033 7037
42. O. Lavergne, J. Harnett, A. Rolland, C. Lanco, L. Lesueur-Ginot, D. Demarquay, M. Huchet, H. Coulomb, and D.C. Bigg BN 80927: a novel homocamptothecin with inhibitory activities on both topoisomerase I and topoisomerase II, Bioorg Med. Chem. Lett. 9 1999 2599 2602
43. O. Lavergne, L. Lesueur-Ginot, F.P. Rodas, and D.C.H. Bigg BN 80245: an E-ring modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities Bioorg. Med. Chem. Lett. 7 1997 2235 2238
44. O. Lavergne, D. Demarquay, C. Bailly, C. Lanco, A. Rolland, M. Huchet, H. Coulomb, N. Muller, N. Baroggi, J. Camara, C. Le Breton, E. Manginot, J.B. Cazaux, and D.C. Bigg Topoisomerase I-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins J. Med. Chem. 43 2000 2285 2289
45. Y. Urasaki, Y. Takebayashi, and Y. Pommier Activity of a novel camptothecin analogue, homocamptothecin, in camptothecin-resistant cell lines with topoisomerase I alterations Cancer Res. 60 2000 6577 6580
46. D.F. Kehrer, O. Soepenberg, W.J. Loos, J. Verweij, and A. Sparreboom Modulation of camptothecin analogs in the treatment of cancer: a review Anticancer Drugs 12 2001 89 105
47. D.K. Kim, and N. Lee Recent advances in topoisomerase I-targeting agents, camptothecin analogues Mini Rev. Med. Chem. 2 2002 611 619
48. W. Du Towards new anticancer drugs: a decade of advances in synthesis of camptothecins and related alkaloids Tetrahedron 59 2003 8649 8687
49. Y. Pommier DNA topoisomerase I inhibitors: chemistry, biology, and interfacial inhibition Chem. Rev. 109 2009 2894 2902
50. N.V. Cuong, M.F. Hsieh, and C.M. Huang Recent development in nano-sized dosage forms of plant alkaloid camptothecin-derived drugs Recent Pat. Anticancer Drug Discov. 4 2009 254 261
51. Y. Pommier, E. Leo, H. Zhang, and C. Marchand DNA topoisomerases and their poisoning by anticancer and antibacterial drugs Chem. Biol. 17 2010 421 433
52. V.J. Venditto, and E.E. Simanek Cancer therapies utilizing the camptothecins: a review of the in vivo literature Mol. Pharmaceutics 7 2010 307 349
53. R.W. Driver, and L.X. Yang Synthesis and pharmacology of new camptothecin drugs Mini. Rev. Med. Chem. 5 2005 425 439
54. Y. Pommier Topoisomerase I inhibitors: camptothecins and beyond Nat. Rev. Cancer 6 2006 789 802
55. C. Bailly Homocamptothecins: potent topoisomerase I inhibitors and promising anticancer drugs Crit. Rev. Oncol. Hematol. 45 2003 91 108
56. J.R. Kroep, and H. Gelderblom Diflomotecan, a promising homocamptothecin for cancer therapy Expert Opin. Investig. Drugs 18 2009 69 75
57. B. Teicher Next generation topoisomerase I inhibitors: rationale and biomarker strategies Biochem. Pharm. 75 2008 1262 1271
58. D. Demarquay, M. Huchet, H. Coulomb, L. Lesueur-Ginot, O. Lavergne, P.G. Kasprzyk, C. Bailly, J. Camara, and D.C. Bigg The homocamptothecin BN 80915 is a highly potent orally active topoisomerase I poison Anticancer Drugs 12 2001 9 19
59. A. Lansiaux, M. Facompre, N. Wattez, M.P. Hildebrand, C. Bal, D. Demarquay, O. Lavergne, D.C. Bigg, and C. Bailly Apoptosis induced by the homocamptothecin anticancer drug BN80915 in HL-60 cells Mol. Pharmacol. 60 2001 450 461
60. H. Gelderblom, R. Salazar, J. Verweij, G. Pentheroudakis, M.J.A. de Jonge, M. Devlin, C. van Hooije, F. Seguy, R. Obach, J. Prunonosa, P. Principe, and C. Twelves Phase I pharmacological and bioavailability study of oral diflomotecan (BN80915), a novel E-ring-modified camptothecin analogue in adults with solid tumors Clin. Cancer Res. 9 2003 4101 4107
61. A.K. Larsen, C. Gilbert, G. Chyzak, S.Y. Plisov, I. Naguibneva, O. Lavergne, L. Lesueur-Ginot, and D.C. Bigg Unusual potency of BN 80915, a novel fluorinated E-ring modified camptothecin, toward human colon carcinoma cells Cancer Res. 61 2001 2961 2967
62. J.S. Graham, S. Falk, L.M. Samuel, J.M. Cendros, and T.R. Evans A multi-centre dose-escalation and pharmacokinetic study of diflomotecan in patients with advanced malignancy Cancer Chemother. Pharmacol. 63 2009 945 952
63. L. Lesueur-Ginot, D. Demarquay, R. Kiss, P.G. Kasprzyk, L. Dassonneville, C. Bailly, J. Camara, O. Lavergne, and D.C. Bigg Homocamptothecin, an E-ring modified camptothecin with enhanced lactone stability, retains topoisomerase I-targeted activity and antitumor properties Cancer Res. 59 1999 2939 2943
64. C. Bailly, A. Lansiaux, L. Dassonneville, D. Demarquay, H. Coulomb, M. Huchet, O. Lavergne, and D.C.H. Bigg Homocamptothecin, an E-Ring-modified camptothecin analogue, generates new topoisomerase I-mediated DNA breaks Biochemistry 38 1999 15556 15563
65. D. Demarquay BN80927: a novel homocamptothecin that inhibits proliferation of human tumor cells in vitro and in vivo Cancer Res. 64 2004 4942 4949
66. M. Huchet, D. Demarquay, H. Coulomb, P. Kasprzyk, M. Carlson, J. Lauer, O. Lavergne, and D. Bigg The dual topoisomerase inhibitor, BN 80927, is highly potent against cell proliferation and tumor growth Ann. N. Y. Acad. Sci. 922 2000 303 305
67. D. Demarquay, H. Coulomb, M. Huchet, L. Lesueur-Ginot, J. Camara, O. Lavergne, and D. Bigg The homocamptothecin, BN 80927, is a potent topoisomerase I poison and topoisomerase II catalytic inhibitor Ann. N. Y. Acad. Sci. 922 2000 301 302
68. D. Chauvier, H. Morjani, and M. Manfait Homocamptothecin-daunorubicin association overcomes multidrug-resistance in breast cancer MCF7 cells Breast Can. Res. Treat. 73 2002 113 125
69. D. Chauvier, I. Chourpa, D.C. Bigg, and M. Manfait Kinetics of in vitro hydrolysis of homocamptothecins as measured by fluorescence Ann. N. Y. Acad. Sci. 922 2000 314 316
70. P. Philippart, L. Harper, C. Chaboteaux, C. Decaestecker, Y. Bronckart, L. Gordover, L. Lesueur-Ginot, H. Malonne, O. Lavergne, D.C. Bigg, P.M. da Costa, and R. Kiss 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
71. O. Lavergne, D. Demarquay, P.G. Kasprzyk, and D.C. Bigg Homocamptothecins: E-ring modified CPT analogues Ann. N. Y. Acad. Sci. 922 2000 100 111
72. C. Bailly, W. Laine, B. Baldeyrou, D. Demarquay, M. Huchet, H. Coulomb, C. Lanco, O. Lavergne, and D.C. Bigg A novel B-ring modified homocamptothecin, 12-Cl-hCPT, showing antiproliferative and topoisomerase I inhibitory activities superior to SN-38 Anticancer. Drug Des. 16 2001 27 36
73. D. Bom, D.P. Curran, A.J. Chavan, S. Kruszewski, S.G. Zimmer, K.A. Fraley, and T.G. Burke Novel A, B, E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities J. Med. Chem. 42 1999 3018 3022
74. S. Dallavalle, L. Merlini, G. Morini, L. Musso, S. Penco, G.L. Beretta, S. Tinelli, and F. Zunino Synthesis and cytotoxic activity of substituted 7-aryliminomethyl derivatives of camptothecin Eur. J. Med. Chem. 39 2004 507 513
75. Z. Miao, C. Sheng, W. Zhang, H. Ji, J. Zhang, L. Shao, L. You, M. Zhang, J. Yao, and X. Che New homocamptothecins: synthesis, antitumor activity, and molecular modeling Bioorg. Med. Chem. 16 2008 1493 1510
76. K. Lackey, D.D. Sternbach, D.K. Croom, D.L. Emerson, M.G. Evans, P.L. Leitner, M.J. Luzzio, G. McIntyre, A. Vuong, J. Yates, and J.M. Besterman Water soluble inhibitors of topoisomerase I: quaternary salt derivatives of camptothecin J. Med. Chem. 39 1996 713 719
77. Y.G. Zu, Q.Y. Li, Y.J. Fu, and W. Wang Synthesis and cytotoxicity of water soluble quaternary salt derivatives of camptothecin Bioorg. Med. Chem. Lett. 14 2004 4023 4026
78. L. Zhu, X. Zhang, N. Lei, W. Liu, Z. Miao, C. Zhuang, C. Sheng, W. Guo, G. Dong, J. Yao, P. Cheng, and W. Zhang Synthesis and biological evaluation of 7-alkenyl homocamptothecins as potent topoisomerase I inhibitors Chem. Biodivers. 9 2012 1084 1094
79. L. You, W. Zhang, Z. Miao, W. Guo, X. Che, W. Wang, C. Sheng, J. Yao, and T. Zhou Synthesis and antitumor activity of novel 10-amino acids ester homocamptothecin analogues Chin. Chem. Lett. 19 2008 811 813
80. Z. Miao, J. Zhang, L. You, J. Wang, C. Sheng, J. Yao, W. Zhang, H. Feng, W. Guo, L. Zhou, W. Liu, L. Zhu, P. Cheng, X. Che, W. Wang, C. Luo, Y. Xu, and G. Dong Phosphate ester derivatives of homocamptothecin: synthesis, solution stabilities and antitumor activities Bioorg. Med. Chem. 18 2010 3140 3146
81. W. Guo, Z. Miao, C. Sheng, J. Yao, H. Feng, W. Zhang, L. Zhu, W. Liu, P. Cheng, J. Zhang, X. Che, W. Wang, C. Luo, and Y. Xu Synthesis and evaluation of 9-benzylideneamino derivatives of homocamptothecin as potent inhibitors of DNA topoisomerase I Eur. J. Med. Chem. 45 2010 2223 2228
82. W. Guo, Z. Miao, C. Sheng, J. Yao, W. Liu, L. Zhu, Y. Zhang, P. Cheng, G. Dong, C. Zhuang, and W. Zhang Synthesis of 9-(heteroarylmethylidene)amino derivatives of homocamptothecin with biological activities Chem. Biodivers. 8 2011 1266 1273
83. L. Zhu, Z. Miao, C. Sheng, W. Guo, J. Yao, W. Liu, X. Che, W. Wang, P. Cheng, and W. Zhang Trifluoromethyl-promoted homocamptothecins: synthesis and biological activity Eur. J. Med. Chem. 45 2010 2726 2732
84. W. Guo, W. Liu, L. Zhu, Y. Zhang, P. Cheng, G. Dong, C. Zhuang, J. Yao, C. Sheng, Z. Miao, and W. Zhang Topoisomerase I-mediated antiproliferative activity of 10-substituted and 12-substituted homocamptothecins Chem. Biodivers. 8 2011 1539 1549
85. C.O. Kappe Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog Acc. Chem. Res. 33 2000 879 888
86. T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, and T.J. Mitchison Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen Science 286 1999 971 974
87. D. Russowsky, R.F. Canto, S.A. Sanches, M.G. D'Oca, A. de Fatima, R.A. Pilli, L.K. Kohn, M.A. Antonio, and J.E. de Carvalho Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: monastrol, oxo-monastrol and oxygenated analogues Bioorg. Chem. 34 2006 173 182
88. L. Zhu, P. Cheng, N. Lei, J. Yao, C. Sheng, C. Zhuang, W. Guo, W. Liu, Y. Zhang, G. Dong, S. Wang, Z. Miao, and W. Zhang Synthesis and biological evaluation of novel homocamptothecins conjugating with dihydropyrimidine derivatives as potent topoisomerase I inhibitors Arch. Pharm. 344 2011 726 734
89. G. Giannini, M. Marzi, W. Cabri, E. Marastoni, G. Battistuzzi, L. Vesci, C. Pisano, G.L. Beretta, M.D. Cesare, and F. Zunino E-ring-modified 7-oxyiminomethyl camptothecins: synthesis and preliminary in vitro and in vivo biological evaluation Bioorg. Med. Chem. Lett. 18 2008 2910 2915
90. Y. Luo, S. Yu, L. Tong, Q. Huang, W. Lu, and Y. Chen Synthesis and biological evaluation of new homocamptothecin analogs Eur. J. Med. Chem. 54 2012 281 286
91. W. Du, D.P. Curran, R.L. Bevins, S.G. Zimmer, J. Zhang, and T.G. Burke Synthesis and evaluation of a novel E-ring modified alpha-hydroxy keto ether analogue of camptothecin Bioorg. Med. Chem. 10 2002 103 110
92. G.S. Laco, W. Du, G. Kohlhagen, J.M. Sayer, D.M. Jerina, T.G. Burke, D.P. Curran, and Y. Pommier Analysis of human topoisomerase I inhibition and interaction with the cleavage site +1 deoxyguanosine, via in vitro experiments and molecular modeling studies Bioorg. Med. Chem. 12 2004 5225 5235
93. R. Tangirala, S. Antony, K. Agama, Y. Pommier, B. Anderson, R. Bevins, and D. Curran Synthesis and biological assays of E-ring analogs of camptothecin and homocamptothecin Bioorg. Med. Chem. 14 2006 6202 6212
94. W.A. Denny Prodrug strategies in cancer therapy Eur. J. Med. Chem. 36 2001 577 595
95. F.H. Hausheer, J. Wang, H. Kochat, Camptothecin-analog with a novel, flipped lactone-stable, E-ring and methods for making and using same. WO2007123995 (2007).
96. H.-G. Lerchen, B.K. Von Dem, J. Baumgarten, M. Sperzel, Glycoconjugates from modified camptothecin derivatives (20-O-linkage). US6492335 (2002).
97. M.E. Wall, M.C. Wani, A.W. Nicholas, G. Manikumar, C. Tele, L. Moore, A. Truesdale, P. Leitner, and J.M. Besterman Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs J. Med. Chem. 36 1993 2689 2700
98. R.S. Tangirala, R. Dixon, D. Yang, A. Ambrus, S. Antony, K. Agama, Y. Pommier, and D.P. Curran Total and semisynthesis and in vitro studies of both enantiomers of 20-fluorocamptothecin Bioorg. Med. Chem. Lett. 15 2005 4736 4740
99. T. Toru, N. Shibata, T. Ishimaru, and M. Nakamura 20-Deoxy-20- fluorocamptothecin: design and synthesis of camptothecin isostere Synletters 2004 2509 2512
100. R.M. Wadkins, P.M. Potter, B. Vladu, J. Marty, G. Mangold, S. Weitman, G. Manikumar, M.C. Wani, M.E. Wall, and D.D. Von Hoff Water soluble 20(S)-glycinate esters of 10,11-methylenedioxycamptothecins are highly active against human breast cancer xenografts Cancer Res. 59 1999 3424 3428
101. X. Liu, J. Zhang, L. Song, B.C. Lynn, and T.G. Burke Degradation of camptothecin-20(S)-glycinate ester prodrug under physiological conditions J. Pharm. Biomed. Anal. 35 2004 1113 1125
102. L. Song, R. Bevins, and B.D. Anderson Kinetics and mechanisms of activation of α-amino acid ester prodrugs of camptothecins J. Med. Chem. 49 2006 4344 4355
103. X. Liu, B.C. Lynn, J. Zhang, L. Song, D. Bom, W. Du, D.P. Curran, and T.G. Burke A versatile prodrug approach for liposomal core-loading of water-insoluble camptothecin anticancer drugs J. Am. Chem. Soc. 124 2002 7650 7651
104. F.M. de Groot, G.F. Busscher, R.W. Aben, and H.W. Scheeren Novel 20-carbonate linked prodrugs of camptothecin and 9-aminocamptothecin designed for activation by tumour-associated plasmin Bioorg. Med. Chem. Lett. 12 2002 2371 2376
105. B.A. Hanson, R.L. Schowen, and V.J. Stella A mechanistic and kinetic study of the E-ring hydrolysis and lactonization of a novel phosphoryloxymethyl prodrug of camptothecin Pharm. Res. 20 2003 1031 1038
106. S.-S. Jew, M.G. Kim, H.-J. Kim, E.-Y. Roh, Y.-S. Cho, J.-K. Kim, K.-H. Cha, K.-K. Lee, H.-J. Han, and H. Lee Synthesis and in vitro cytotoxicity of (RS)-20-desethyl-20-substituted camptothecin analogues Bioorg. Med. Chem. Lett. 6 1996 849 852
107. S.-S. Jew, M.G. Kim, H.-J. Kim, E.-Y. Rho, H.-G. Park, J.-K. Kim, H.-J. Han, and H. Lee Synthesis and in vitro cytotoxicity of C(20)(RS)-camptothecin analogues modified at both B (or A) and E ring Bioorg. Med. Chem. Lett. 8 1998 1797 1800
108. N.J. Rahier, B.M. Eisenhauer, R. Gao, S.J. Thomas, and S.M. Hecht On the role of E-ring oxygen atoms in the binding of camptothecin to the topoisomerase I-DNA covalent binary complex Bioorg. Med. Chem. 13 2005 1381 1386
109. E. Riva, D. Comi, S. Borrelli, F. Colombo, B. Danieli, J. Borlak, L. Evensen, J.B. Lorens, G. Fontana, O.M. Gia, L.D. Via, and D. Passarella Synthesis and biological evaluation of new camptothecin derivatives obtained by modification of position 20 Bioorg. Med. Chem. 18 2010 8660 8668
110. X. Xiao, and M. Cushman Effect of E-ring modifications in camptothecin on topoisomerase I inhibition: a quantum mechanics treatment J. Org. Chem. 70 2005 9584 9587
111. G.S. Laco, J.R. Collins, B.T. Luke, H. Kroth, J.M. Sayer, D.M. Jerina, and Y. Pommier Human topoisomerase I inhibition: docking camptothecin and derivatives into a structure-based active site Model Biochemistry 41 2002 1428 1435
112. L. Zhu, C. Zhuang, N. Lei, Z. Guo, C. Sheng, G. Dong, S. Wang, Y. Zhang, J. Yao, Z. Miao, and W. Zhang Synthesis and preliminary bioevaluation of novel E-ring modified acetal analog of camptothecin as cytotoxic agents Eur. J. Med. Chem. 56 2012 1 9
113. S. Cananzi, S. Dallavalle, A. Bargiotti, L. Merlini, R. Artali, and G.L. Beretta Synthesis of new cytotoxic E-ring modified camptothecins Tetrahedron Lett. 51 2010 6489 6492
114. A. Cagir, S.H. Jones, R. Gao, B.M. Eisenhauer, S.M. Hecht, and A. Luotonin A naturally occurring human DNA topoisomerase I poison J. Am. Chem. Soc. 125 2003 13628 13629
115. B.M. Fox, X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier, B.L. Staker, L. Stewart, and M. Cushman Design, synthesis, and biological evaluation of cytotoxic 11-alkenylindenoisoquinoline topoisomerase I inhibitors and indenoisoquinoline-camptothecin hybrids J. Med. Chem. 46 2003 3275 3282
116. K. Cheng, N.J. Rahier, B.M. Eisenhauer, R. Gao, S.J. Thomas, and S.M. Hecht 14-Azacamptothecin: a potent water-soluble topoisomerase I poison J. Am. Chem. Soc. 127 2005 838 839
117. A. Cagir, S.H. Jones, B.M. Eisenhauer, R. Gao, and S.M. Hecht Synthesis and biochemical properties of E-ring modified luotonin A derivatives Bioorg. Med. Chem. Lett. 14 2004 2051 2054
118. L.Z. Lin, and G.A. Cordell Quinoline alkaloids from Camptotheca acuminata Phytochemistry 28 1989 1295 1297
119. X. Xiao, S. Antony, Y. Pommier, and M. Cushman Total synthesis and biological evaluation of 22-hydroxyacuminatine J. Med. Chem. 49 2006 1408 1412
120. K. Nacro, C. Zha, P.R. Guzzo, R. Jason Herr, D. Peace, and T.D. Friedrich Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives Bioorg. Med. Chem. 15 2007 4237 4246
121. S. Dallavalle, L. Merlini, G.L. Beretta, S. Tinelli, and F. Zunino Synthesis and cytotoxic activity of substituted luotonin A derivatives Bioorg. Med. Chem. Lett. 14 2004 5757 5761
122. V.A. Bacherikov, T.-J. Tsai, J.-Y. Chang, T.-C. Chou, R.-Z. Lee, and T.-L. Su Synthesis of new camptothecin analogues with the E-Lactone ring replaced by α,β-cyclohexenone Eur. J. Org. Chem. 2006 2006 4490 4499
123. M. Li, W. Tang, F. Zeng, L. Lou, and T. You Semi-synthesis and biological activity of gamma-lactones analogs of camptothecin Bioorg. Med. Chem. Lett. 18 2008 6441 6443
124. P. Hautefaye, B. Cimetière, A. Pierré, S. Léonce, J. Hickman, W. Laine, C. Bailly, and G. Lavielle Synthesis and pharmacological evaluation of novel non-lactone analogues of camptothecin Bioorg. Med. Chem. Lett. 13 2003 2731 2735
125. A. Lansiaux, S. Leonce, L. Kraus-Berthier, C. Bal-Mahieu, R. Mazinghien, S. Didier, M.H. David-Cordonnier, P. Hautefaye, G. Lavielle, C. Bailly, J.A. Hickman, and A. Pierre Novel stable camptothecin derivatives replacing the E-ring lactone by a ketone function are potent inhibitors of topoisomerase I and promising antitumor drugs Mol. Pharmacol. 72 2007 311 319
126. K. Takagi, T.S. Dexheimer, C. Redon, O. Sordet, K. Agama, G. Lavielle, A. Pierre, S.E. Bates, and Y. Pommier Novel E-ring camptothecin keto analogues (S38809 and S39625) are stable, potent, and selective topoisomerase I inhibitors without being substrates of drug efflux transporters Mol. Cancer Ther. 6 2007 3229 3238
127. T. Sugasawa, T. Toyoda, N. Uchida, and K. Yamaguchi Experiments of synthesis of dl-camptothecin. 4. Synthesis and antileukemic activity of dl-camptothecin analogues J. Med. Chem. 19 1976 675 679
128. R.T. Crow, and D.M. Crothers Structural modifications of camptothecin and effects on topoisomerase I inhibition J. Med. Chem. 35 1992 4160 4164
129. G.L. Beretta, G. Petrangolini, M. De Cesare, G. Pratesi, P. Perego, S. Tinelli, M. Tortoreto, M. Zucchetti, R. Frapolli, E. Bello, C. Manzotti, G. Fontana, E. Bombardelli, A. Battaglia, C. Samori, and F. Zunino Biological properties of IDN5174, a new synthetic camptothecin with the open lactone ring Cancer Res. 66 2006 10976 10982
130. T. Yaegashi, S. Sawada, H. Nagata, T. Furuta, T. Yokokura, and T. Miyasaka 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. 42 1994 2518 2525
131. G.S. Manning, and J. Ray Counterion condensation revisited J. Biomol. Struct. Dyn. 16 1998 461 476
132. Y. Pommier, and M. Cushman The indenoisoquinoline noncamptothecin topoisomerase I inhibitors: update and perspectives Mol. Cancer Ther. 8 2009 1008 1014
133. C. Sheng, Z. Miao, and W. Zhang New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors Curr. Med. Chem. 18 2011 4389 4409