Design, synthesis, mechanisms of action, and toxicity of novel 20(s)-sulfonylamidine derivatives of camptothecin as potent antitumor agents

Journal of Medicinal Chemistry

Volumn 57, Issue 14, 2014, Pages 6008-6018

  Wang, Mei Juan ^a   Liu, Ying Qian ^a   Chang, Ling Chu ^b   Wang, Chih Ya ^c   Zhao, Yong Long ^a   Zhao, Xiao Bo ^a   Qian, Keduo ^c   Nan, Xiang ^a   Yang, Liu ^d   Yang, Xiao Ming ^c   Hung, Hsin Yi ^b   Yang, Jai Sing ^b   Kuo, Daih Huang ^e   Goto, Masuo ^c   Morris Natschke, Susan L ^c   Pan, Shiow Lin ^f   Teng, Che Ming ^g   Kuo, Sheng Chu ^b   Wu, Tian Shung ^h   Wu, Yang Chang ^b   Lee, Kuo Hsiung ^b,c   more..

^a LANZHOU UNIVERSITY   (China)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

^c University of North Carolina   (United States)

^d LANZHOU JIAOTONG UNIVERSITY   (China)

^e TAJEN UNIVERSITY   (Taiwan)

^f TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^g NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^h NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CAMPTOTHECIN DERIVATIVE; IRINOTECAN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMIDINES; ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CAMPTOTHECIN; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; DNA TOPOISOMERASES, TYPE I; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HCT116 CELLS; HUMANS; KB CELLS; MICE; MICE, INBRED BALB C; MICE, NUDE; MOLECULAR CONFORMATION; NEOPLASMS, EXPERIMENTAL; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TOPOISOMERASE I INHIBITORS;

EID: 84905014952     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm5003588     Document Type: Article

References (36)

1. Wall, M. E.; Wani, M.; 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. 1966, 88, 3888-3890
2. Wang, H. K.; Morris-Natschke, S. L.; Lee, K. H. Antitumor agents 170. Recent advances in the discovery and development of topoisomerase inhibitors as antitumor agents Med. Res. Rev. 1997, 17, 367-425 and literature cited therein.
3. Oberlies, N. H.; Kroll, D. J. Camptothecin and taxol: historic achievements in natural products research J. Nat. Prod. 2004, 67, 129-135
4. Hsiang, Y. H.; Hertzberg, R.; Hecht, S. M.; Liu, L. F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I J. Biol. Chem. 1985, 260, 14873-14878
5. Pommier, Y.; Kohlhagen, G. K.; Kohn, K. W.; Leteurtre, F.; Wani, M. C.; Wall, M. E. Interaction of an alkylating camptothecin derivative with a DNA base at topoisomerase I-DNA cleavage sites Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8861-8865
6. Liew, S. T.; Yang, L. X. Design, synthesis and development of novel camptothecin drugs Curr. Pharm. Des. 2008, 14, 1078-1097
7. Li, Q. Y.; Zu, Y. G.; Shi, R. Z.; Yao, L. P. Review camptothecin: current perspectives Curr. Med. Chem. 2006, 13, 2021-2039
8. Rahier, N. J.; Thomas, C. J.; Hecht, S. M. Camptothecin and Its Analogs. In Anticancer Agents from Natural Products; Cragg, G. M.; Kingston, D. G. I.; Newman, D. J., Eds.; CRC Press: New York, 2012; pp 5-21, and literature cited therein.
9. Adams, D. J. The impact of tumor physiology on camptothecin-based drug development Curr. Med. Chem.: Anti-Cancer Agents 2005, 5, 1-13
10. Tobin, P. J.; Rivory, L. P. Camptothecins and key lessons in drug design Drug Des. Rev. 2004, 1, 341-346
11. Hatefi, A.; Amsden, B. Camptothecin delivery methods Pharm. Res. 2002, 19, 1389-1399
12. Onishi, H.; Machida, Y. Macromolecular and nanotechnological modification of camptothecin and its analogs to improve the efficacy Curr. Drug Discovery Technol. 2005, 2, 169-183
13. Sirikantaramas, S.; Asano, T.; Sudo, H.; Yamazaki, M.; Saito, K. Camptothecin: therapeutic potential and biotechnology Curr. Pharm. Biotechnol. 2007, 8, 196-202
14. Fassberg, J.; Stella, V. J. A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues J. Pharm. Sci. 1992, 81, 676-684
15. Zhao, H.; Lee, C.; Sai, P.; Choe, Y. H.; Boro, M.; Pendri, A.; Guan, S.; Greenwald, R. B. 20- O -Acylcamptothecin derivatives: evidence for lactone stabilization J. Org. Chem. 2000, 65, 4601-4606
16. Liu, Y. Q.; Tian, X.; Yang, L.; Zhan, Z. C. First synthesis of novel spin-labeled derivatives of camptothecin as potential antineoplastic agents Eur. J. Med. Chem. 2008, 43, 2610-2614
17. Yang, L.; Zhao, C. Y.; Liu, Y. Q. Synthesis and biological evaluation of novel conjugates of camptothecin and 5-flurouracil as cytotoxic agents J. Braz. Chem. Soc. 2011, 22, 308-318
18. Yang, L. X.; Pan, X.; Wang, H. J. Novel camptothecin derivatives. Part 1: oxyalkanoic acid esters of camptothecin and their in vitro and in vivo antitumor activity Bioorg. Med. Chem. Lett. 2002, 12, 1241-1244
19. Cao, Z.; Harris, N.; Kozielski, A.; Vardeman, D.; Stehlin, J. S.; Giovanella, B. Alkyl esters of camptothecin and 9-nitrocamptothecin: synthesis, in vitro pharmacokinetics, toxicity, and antitumor activity J. Med. Chem. 1998, 41, 31-37
20. De Groot, F. M. H.; Busscher, G. F.; Aben, R. W. M.; Scheeren, H. W. Novel 20-carbonate linked prodrugs of camptothecin and 9-aminocamptothecin designed for activation by tumour-associated plasmin Bioorg. Med. Chem. Lett. 2002, 12, 2371-2376
21. Lerchen, H. G.; Baumgarten, J.; von dem Bruch, K.; Lehmann, T. E.; Sperzel, M.; Kempka, G.; Fiebig, H. H. Design and optimization of 20- O -linked camptothecin glycoconjugates as anticancer agents J. Med. Chem. 2001, 44, 4186-4195
22. Greenhill, J. V.; Lue, P. Amidines and guanidines in medicinal chemistry Prog. Med. Chem. 1993, 30, 203-326
23. Rauws, T. R. M.; Maes, B. U. W. Transition metal-catalyzed N -arylations of amidines and guanidines Chem. Soc. Rev. 2012, 41, 2463-2497
24. Sondhi, S. M.; Dinodia, M.; Jain, S.; Kumar, A. Synthesis of biologically active N -methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride Eur. J. Med. Chem. 2008, 43, 2824-2830
25. Rahmathullah, S. M.; Hall, J. E.; Bender, B. C.; McCurdy, D. R.; Tidwell, R. R.; Boykin, D. W. Prodrugs for amidines: synthesis and anti-pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl)furan J. Med. Chem. 1999, 42, 3994-4000
26. Casini, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Sulfonamides and sulfonylated derivatives as anticancer agents Curr. Cancer Drug Targets 2002, 2, 55-75
27. Nishino, R.; Ikeda, K.; Hayakawa, T.; Takahashi, T.; Suzuki, T.; Sato, M. Syntheses of 2-deoxy-2,3-didehydro- N -acetylneuraminic acid analogues modified by N -sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1 Bioorg. Med. Chem. 2011, 19, 2418-2427
28. Takasuna, K.; Kasai, Y.; Kitano, Y.; Mori, K.; Kobayashi, R.; Hagiwara, T.; Kakihata, K.; Hirohashi, M.; Nomura, M.; Nagai, E. Protective effects of kampo medicine and baicalin against intestinal toxicity of a new anticancer camptothecin derivative, irinotecan hydrochloride (CPT-11), in rats Jpn. J. Cancer Res. 1995, 86, 978-984
29. Bae, I.; Han, H.; Chang, S. Highly efficient one-pot synthesis of N -sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine J. Am. Chem. Soc. 2005, 127, 2038-2039
30. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 1990, 82, 1107-1112
31. Li, T. K.; Liu, L. F. Tumor cell death induced by topoisomerase-targeting drugs Annu. Rev. Pharmacol. Toxicol. 2001, 41, 53-77
32. Desai, S. D.; Zhang, H.; Rodriguez-Bauman, A.; Yang, J. M.; Wu, X.; Gounder, M. K.; Rubin, E. H.; Liu, L. F. Transcription-dependent degradation of topoisomerase I-DNA covalent complexes Mol. Cell. Biol. 2003, 23, 2341-2350
33. Takemura, H.; Rao, V. A.; Sordet, O.; Furuta, T.; Miao, Z. H.; Meng, L.; Zhang, H.; Pommier, Y. Defective Mre11-dependent activation of Chk2 by ataxia telangiectasia mutated in colorectal carcinoma cells in response to replication-dependent DNA double strand breaks J. Biol. Chem. 2006, 281, 30814-30823
34. Kastan, M. B.; Bartek, J. Cell-cycle checkpoints and cancer Nature 2004, 432, 316-323
35. Kunimoto, T.; Nitta, K.; Tanaka, T.; Uehara, N.; Baba, H.; Takeuchi, M.; Yokokura, T.; Sawada, S.; Miyasaka, T.; Mutai, M. Antitumor activity of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothecin, a novel water-soluble derivative of camptothecin, against murine tumors Cancer Res. 1987, 47, 5944-5947
36. Shackelford, C.; Long, G.; Wolf, J.; Okerberg, C.; Herbert, R. Qualitative and quantitative analysis of nonneoplastic lesions in toxicology studies Toxicol. Pathol. 2002, 30, 93-96