Novel DNA intercalators without basic side chains as efficient antitumor agents: Design, synthesis and evaluation of benzo-[c,d]-indol-malononitrile derivatives

Xiaolian Li; Qianqian Wang; Yang Qing; Yanjie Lin; Yingli Zhang; Xuhong Qian; Jingnan Cui

doi:10.1016/j.bmc.2010.03.017

Novel DNA intercalators without basic side chains as efficient antitumor agents: Design, synthesis and evaluation of benzo-[c,d]-indol-malononitrile derivatives

Xiaolian Li
, Qianqian Wang
, Yang Qing
, Yanjie Lin
, Yingli Zhang
, Xuhong Qian^*
, Jingnan Cui

^*Corresponding author for this work

Dalian University of Technology
East China University of Science and Technology

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

Several 2-(substituted benzo[c,d]indol-2(1H)-ylidene)malononitriles have been designed and synthesized. Their DNA binding, antitumor and DNA damaging properties were evaluated. All the compounds exhibited efficient antitumor activities with preference to be against the tumor cell line 7721 rather than the tumor cell line MCF-7. Compound 1f could intercalate into DNA entirely presumably by the good conjugation of carbonyl group with benzo[c,d]indol moiety. What's more, 1f exhibited potent toxicity against MCF-7 cells with IC₅₀ at 0.003 μM and against 7721 cells at 0.115 μM, respectively.

Original language	English
Pages (from-to)	3279-3284
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2010.03.017
State	Published - 1 May 2010
Externally published	Yes

Keywords

Antitumor agents
Benzo[c,d]indol-2(1H)-one
DNA cleavage
DNA intercalator

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10.1016/j.bmc.2010.03.017

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title = "Novel DNA intercalators without basic side chains as efficient antitumor agents: Design, synthesis and evaluation of benzo-[c,d]-indol-malononitrile derivatives",

abstract = "Several 2-(substituted benzo[c,d]indol-2(1H)-ylidene)malononitriles have been designed and synthesized. Their DNA binding, antitumor and DNA damaging properties were evaluated. All the compounds exhibited efficient antitumor activities with preference to be against the tumor cell line 7721 rather than the tumor cell line MCF-7. Compound 1f could intercalate into DNA entirely presumably by the good conjugation of carbonyl group with benzo[c,d]indol moiety. What's more, 1f exhibited potent toxicity against MCF-7 cells with IC50 at 0.003 μM and against 7721 cells at 0.115 μM, respectively.",

keywords = "Antitumor agents, Benzo[c,d]indol-2(1H)-one, DNA cleavage, DNA intercalator",

author = "Xiaolian Li and Qianqian Wang and Yang Qing and Yanjie Lin and Yingli Zhang and Xuhong Qian and Jingnan Cui",

year = "2010",

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doi = "10.1016/j.bmc.2010.03.017",

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TY - JOUR

T1 - Novel DNA intercalators without basic side chains as efficient antitumor agents

T2 - Design, synthesis and evaluation of benzo-[c,d]-indol-malononitrile derivatives

AU - Li, Xiaolian

AU - Wang, Qianqian

AU - Qing, Yang

AU - Lin, Yanjie

AU - Zhang, Yingli

AU - Qian, Xuhong

AU - Cui, Jingnan

PY - 2010/5/1

Y1 - 2010/5/1

N2 - Several 2-(substituted benzo[c,d]indol-2(1H)-ylidene)malononitriles have been designed and synthesized. Their DNA binding, antitumor and DNA damaging properties were evaluated. All the compounds exhibited efficient antitumor activities with preference to be against the tumor cell line 7721 rather than the tumor cell line MCF-7. Compound 1f could intercalate into DNA entirely presumably by the good conjugation of carbonyl group with benzo[c,d]indol moiety. What's more, 1f exhibited potent toxicity against MCF-7 cells with IC50 at 0.003 μM and against 7721 cells at 0.115 μM, respectively.

AB - Several 2-(substituted benzo[c,d]indol-2(1H)-ylidene)malononitriles have been designed and synthesized. Their DNA binding, antitumor and DNA damaging properties were evaluated. All the compounds exhibited efficient antitumor activities with preference to be against the tumor cell line 7721 rather than the tumor cell line MCF-7. Compound 1f could intercalate into DNA entirely presumably by the good conjugation of carbonyl group with benzo[c,d]indol moiety. What's more, 1f exhibited potent toxicity against MCF-7 cells with IC50 at 0.003 μM and against 7721 cells at 0.115 μM, respectively.

KW - Antitumor agents

KW - Benzo[c,d]indol-2(1H)-one

KW - DNA cleavage

KW - DNA intercalator

UR - https://www.scopus.com/pages/publications/77951206852

U2 - 10.1016/j.bmc.2010.03.017

DO - 10.1016/j.bmc.2010.03.017

M3 - 文章

C2 - 20385497

AN - SCOPUS:77951206852

SN - 0968-0896

VL - 18

SP - 3279

EP - 3284

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 9

ER -

Novel DNA intercalators without basic side chains as efficient antitumor agents: Design, synthesis and evaluation of benzo-[c,d]-indol-malononitrile derivatives

Abstract

Keywords

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