Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells

被引:34
作者
Tandon, Vishnu K. [1 ]
Maurya, Hardesh K. [2 ]
Kumar, Sandeep [3 ]
Rashid, Aijaz [4 ]
Panda, Dulal [4 ]
机构
[1] Inst Engn & Technol, Dept Appl Sci, Lucknow 226020, Uttar Pradesh, India
[2] Cent Inst Med & Aromat Plants, Med Chem Dept, Lucknow 226015, Uttar Pradesh, India
[3] Univ Lucknow, Dept Chem, Lucknow 226007, Uttar Pradesh, India
[4] Indian Inst Technol, Dept Biosci & Bioengn, Bombay 400076, Maharashtra, India
来源
RSC ADVANCES | 2014年 / 4卷 / 24期
关键词
BIOLOGICAL EVALUATION; 1,4-NAPHTHOQUINONE DERIVATIVES; ANTIBACTERIAL AGENTS; NUCLEOPHILIC-SUBSTITUTION; KINETIC STABILIZATION; MICROTUBULE DYNAMICS; AQUEOUS SUSPENSION; ANTICANCER AGENTS; ANTIFUNGAL AGENTS; ORGANIC-REACTIONS;
D O I
10.1039/c3ra47720g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This article describes the preparation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones by an environmentally benign short synthetic route with the goal of finding 1,4-naphthoquinone derivatives that induce apoptosis in cancer cells. We have identified three most active naphthoquinones 10, 12 and 15 that potently induce apoptosis in human cervical carcinoma (HeLa) cells. One of these three compounds perturbed both microtubule and actin filaments.
引用
收藏
页码:12441 / 12447
页数:7
相关论文
共 37 条
[1]   Curcumin suppresses the dynamic instability of microtubules, activates the mitotic checkpoint and induces apoptosis in MCF-7 cells [J].
Banerjee, Mithu ;
Singh, Parminder ;
Panda, Dulal .
FEBS JOURNAL, 2010, 277 (16) :3437-3448
[2]  
Becker H., 1973, PRACTICAL HDB ORGANI, P611
[3]   5-Substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials [J].
Biot, C ;
Bauer, H ;
Schirmer, RH ;
Davioud-Charvet, E .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5972-5983
[4]   Parallel synthesis and cytotoxicity evaluation of a polyamine-quinone conjugates library [J].
Bolognesi, Maria Laura ;
Calonghi, Natalia ;
Mangano, Chiara ;
Masotti, Lanfranco ;
Melchiorre, Carlo .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (17) :5463-5467
[5]   Synthesis and cytotoxicity of new aminoterpenylquinones [J].
del Corral, JMM ;
Castro, MA ;
Gordaliza, M ;
Martin, ML ;
Gualberto, SA ;
Gamito, AM ;
Cuevas, C ;
San Feliciano, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (03) :631-644
[6]   Nitrogen-containing Heterocyclic quinones: A class of potential selective antitumor agents [J].
Garuti, Laura ;
Roberti, Marinella ;
Pizzirani, Daniela .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (05) :481-489
[7]   CIL-102 binds to tubulin at colchicine binding site and triggers apoptosis in MCF-7 cells by inducing monopolar and multinucleated cells [J].
Gireesh, K. K. ;
Rashid, Aijaz ;
Chakraborti, Soumyananda ;
Panda, Dulal ;
Manna, Tapas .
BIOCHEMICAL PHARMACOLOGY, 2012, 84 (05) :633-645
[8]   Synthesis and cytotoxic evaluation of novel spirohydantoin derivatives of the dihydrothieno[2,3-b]naphtho-4,9-dione system [J].
Gomez-Monterrey, I ;
Santelli, G ;
Campiglia, P ;
Califano, D ;
Falasconi, F ;
Pisano, C ;
Vesci, L ;
Lama, T ;
Grieco, P ;
Novellino, E .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) :1152-1157
[9]   Reactions of C-H bonds in water [J].
Herrerias, Clara I. ;
Yao, Xiaoquan ;
Li, Zhiping ;
Li, Chao-Jun .
CHEMICAL REVIEWS, 2007, 107 (06) :2546-2562
[10]   Nuclear translocation of caspase-3 is dependent on its proteolytic activation and recognition of a substrate-like protein(s) [J].
Kamada, S ;
Kikkawa, U ;
Tsujimoto, Y ;
Hunter, T .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (02) :857-860