Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues
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Citações na Scopus
56
Tipo de produção
article
Data de publicação
2014
Título da Revista
ISSN da Revista
Título do Volume
Editora
PUBLIC LIBRARY SCIENCE
Autores
AMARAL, Daniel Nascimento do
CAVALCANTI, Bruno C.
BEZERRA, Daniel P.
FERREIRA, Paulo Michel P.
CASTRO, Rosane de Paula
SABINO, Jose Ricardo
PESSOA, Claudia
SANT'ANNA, Carlos M. R.
Citação
PLOS ONE, v.9, n.3, article ID e85380, 16p, 2014
Resumo
Cancer is the second most common cause of death in the USA. Among the known classes of anticancer agents, the microtubule-targeted antimitotic drugs are considered to be one of the most important. They are usually classified into microtubule-destabilizing (e. g., Vinca alkaloids) and microtubule-stabilizing (e. g., paclitaxel) agents. Combretastatin A4 (CA-4), which is a natural stilbene isolated from Combretum caffrum, is a microtubule-destabilizing agent that binds to the colchicine domain on beta-tubulin and exhibits a lower toxicity profile than paclitaxel or the Vinca alkaloids. In this paper, we describe the docking study, synthesis, antiproliferative activity and selectivity index of the N-acylhydrazone derivatives (5a-r) designed as CA-4 analogues. The essential structural requirements for molecular recognition by the colchicine binding site of beta-tubulin were recognized, and several compounds with moderate to high antiproliferative potency (IC50 values <= 18 mu M and >= 4 nM) were identified. Among these active compounds, LASSBio-1586 (5b) emerged as a simple antitumor drug candidate, which is capable of inhibiting microtubule polymerization and possesses a broad in vitro and in vivo antiproliferative profile, as well as a better selectivity index than the prototype CA-4, indicating improved selective cytotoxicity toward cancer cells.
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Referências
- Andrade MM, 2010, J COMB CHEM, V12, P245, DOI 10.1021/cc9001444
- Bai RL, 2000, J BIOL CHEM, V275, P40443, DOI 10.1074/jbc.M005299200
- Baxter CA, 1998, PROTEINS, V33, P367, DOI 10.1002/(SICI)1097-0134(19981115)33:3<367::AID-PROT6>3.0.CO;2-W
- BONNE D, 1985, J BIOL CHEM, V260, P2819
- Borchhardt DM, 2010, J BRAZIL CHEM SOC, V21, P142, DOI 10.1590/S0103-50532010000100021
- Cao XF, 2011, J CHIN CHEM SOC-TAIP, V58, P35
- Combes S, 2011, J MED CHEM, V54, P3153, DOI 10.1021/jm901826e
- Desai A, 1997, ANNU REV CELL DEV BI, V13, P83, DOI 10.1146/annurev.cellbio.13.1.83
- DEWAR MJS, 1985, J AM CHEM SOC, V107, P3902, DOI 10.1021/ja00299a024
- Dorleans A, 2009, P NATL ACAD SCI USA, V33, P13775
- Ducki S, 1998, BIOORG MED CHEM LETT, V8, P1051, DOI 10.1016/S0960-894X(98)00162-0
- Ducki S, 2009, BIOORGAN MED CHEM, V17, P7711, DOI 10.1016/j.bmc.2009.09.044
- Ducki S, 2009, BIOORGAN MED CHEM, V17, P7698, DOI 10.1016/j.bmc.2009.09.039
- Eldridge MD, 1997, J COMPUT AID MOL DES, V11, P425, DOI 10.1023/A:1007996124545
- Farrugia LJ, 1999, J APPL CRYSTALLOGR, V32, P837, DOI 10.1107/S0021889899006020
- Farrugia LJ, 1997, J APPL CRYSTALLOGR, V30, P565, DOI 10.1107/S0021889897003117
- Furst R, 2009, BIOORG MED CHEM LETT, V19, P6948, DOI 10.1016/j.bmcl.2009.10.064
- Hall LM, 2000, ANTICANCER RES, V20, P903
- HOLLINGSHEAD MG, 1995, LIFE SCI, V57, P131, DOI 10.1016/0024-3205(95)00254-4
- HORWITZ JP, 1954, J ORG CHEM, V19, P194, DOI 10.1021/jo01367a007
- Jin LH, 2006, BIOORG MED CHEM LETT, V16, P5036, DOI 10.1016/j.bmcl.2006.07.048
- Jordan MA, 2004, NAT REV CANCER, V4, P253, DOI 10.1038/nr1317
- Kummerle AE, 2009, EUR J MED CHEM, V44, P4004, DOI 10.1016/j.ejmech.2009.04.044
- Lee L, 2010, J MED CHEM, V53, P325, DOI 10.1021/jm901268n
- Lima PC, 2000, EUR J MED CHEM, V35, P187, DOI 10.1016/S0223-5234(00)00120-3
- MACK CH, 1969, J CHEM ENG DATA, V14, P258, DOI 10.1021/je60041a042
- MAZZONE G, 1978, FARMACO-ED SCI, V33, P963
- Mazzone G, 1991, B SEDUTE ACAD GIONIA, V8, P689
- MOSMANN T, 1983, J IMMUNOL METHODS, V65, P55, DOI 10.1016/0022-1759(83)90303-4
- Nogales E, 2000, ANNU REV BIOCHEM, V69, P277, DOI 10.1146/annurev.biochem.69.1.277
- Prise VE, 2002, INT J ONCOL, V21, P717
- Ravelli RBG, 2004, NATURE, V428, P198, DOI 10.1038/nature02393
- Sadar MD, 2002, MOL CANCER THER, V1, P629
- Schneider P, 2009, PHYTOCHEM LETT, V2, P85, DOI 10.1016/j.phytol.2008.12.004
- Shan Y, 2011, CURR MED CHEM, V18, P523, DOI 10.2174/092986711794480221
- Sheldrick GM, 2008, ACTA CRYSTALLOGR A, V64, P112, DOI 10.1107/S0108767307043930
- Singh P, 2008, IUBMB LIFE, V60, P368, DOI 10.1002/iub.42
- Snyder JP, 2001, P NATL ACAD SCI USA, V98, P5312, DOI 10.1073/pnas.051309398
- Suggitt M, 2004, CLIN CANCER RES, V10, P6677, DOI 10.1158/1078-0432.CCR-04-0855
- Tron GC, 2006, J MED CHEM, V49, P3033, DOI 10.1021/jm0512903
- Workman P, 1998, BRIT J CANCER, V77, P1
- Wermuth GC, 2008, PRACTICE MED CHEM, P448
- Yogeeswari P, 2005, J MED CHEM, V48, P6202, DOI 10.1021/jm050283b