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DNA插入性萘二甲酰亚胺-苯并噻唑/肉桂酰胺衍生物的设计与合成：细胞毒性评估及拓扑异构酶-IIα抑制作用

Design and synthesis of DNA-intercalative naphthalimide-benzothiazole/cinnamide derivatives: cytotoxicity evaluation and topoisomerase-IIα inhibition.

作者信息

Sankara Rao N, Nagesh Narayana, Lakshma Nayak V, Sunkari Satish, Tokala Ramya, Kiranmai Gaddam, Regur Phanindranath, Shankaraiah Nagula, Kamal Ahmed

机构信息

Medicinal Chemistry and Pharmacology , CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007 , India . Email:

Academy of Scientific and Innovative Research. (AcSIR) , CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007 , India.

出版信息

Medchemcomm. 2018 Nov 8;10(1):72-79. doi: 10.1039/c8md00395e. eCollection 2019 Jan 1.

DOI:10.1039/c8md00395e
PMID:30774856
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6350626/
Abstract

A new series of different naphthalimide-benzothiazole/cinnamide derivatives were designed, synthesized and tested for their cytotoxicity on selected human cancer cell lines. Among them, derivatives and with the 6-aminobenzothiazole ring and with the cinnamide ring displayed potent cytotoxic activity against colon (IC: 3.715 and 3.467 μM) and lung cancer (IC: 4.074 and 3.890 μM) cell lines when compared to amonafide (IC: 5.459 and 7.762 μM). Later, the DNA binding studies for these selected derivatives (by CD, UV/vis, fluorescence spectroscopy, DNA viscosity, and molecular docking) suggested that these new derivatives significantly intercalate between two strands of DNA. In addition, the most potent derivatives and were also found to inhibit DNA topoisomerase-II.

摘要

设计、合成了一系列新型的不同萘酰亚胺-苯并噻唑/肉桂酰胺衍生物，并测试了它们对选定人类癌细胞系的细胞毒性。其中，具有6-氨基苯并噻唑环的衍生物和具有肉桂酰胺环的衍生物，与氨茴酸（IC：5.459和7.762 μM）相比，对结肠癌细胞系（IC：3.715和3.467 μM）和肺癌细胞系（IC：4.074和3.890 μM）显示出强大的细胞毒性活性。后来，对这些选定衍生物进行的DNA结合研究（通过圆二色光谱、紫外可见光谱、荧光光谱、DNA粘度和分子对接）表明，这些新衍生物能显著地插入DNA的两条链之间。此外，还发现最具活性的衍生物和也能抑制DNA拓扑异构酶-II。

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本文引用的文献

1
Diverse Targeted Approaches to Battle Multidrug Resistance in Cancer.
Curr Med Chem. 2019;26(39):7059-7080. doi: 10.2174/0929867325666180410110729.
2
Functional 1,8-Naphthalimide AIE/AIEEgens: Recent Advances and Prospects.
ACS Appl Mater Interfaces. 2018 Apr 18;10(15):12081-12111. doi: 10.1021/acsami.7b14473. Epub 2017 Dec 11.
3
Targeting DNA Minor Groove by Hybrid Molecules as Anticancer Agents.
Curr Med Chem. 2017;24(26):2887-2907. doi: 10.2174/0929867324666170523102730.
4
1,8-Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy.
Chem Rec. 2017 Oct;17(10):956-993. doi: 10.1002/tcr.201600134. Epub 2017 Apr 4.
5
Design, antiviral and cytostatic properties of isoxazolidine-containing amonafide analogues.
Bioorg Med Chem. 2015 Jul 1;23(13):3135-46. doi: 10.1016/j.bmc.2015.04.079. Epub 2015 May 6.
6
Naphthalimide derivatives with therapeutic characteristics: a patent review.
Expert Opin Ther Pat. 2013 Mar;23(3):299-317. doi: 10.1517/13543776.2013.746313. Epub 2013 Feb 1.
7
Design and synthesis of benzo[c,d]indolone-pyrrolobenzodiazepine conjugates as potential anticancer agents.
Bioorg Med Chem. 2012 Jan 15;20(2):789-800. doi: 10.1016/j.bmc.2011.12.003. Epub 2011 Dec 14.
8
Promoting the formation and stabilization of human telomeric G-quadruplex DNA, inhibition of telomerase and cytotoxicity by phenanthroline derivatives.
Org Biomol Chem. 2011 Apr 21;9(8):2648-53. doi: 10.1039/c0ob00961j. Epub 2011 Feb 24.
9
DNA topoisomerases and their poisoning by anticancer and antibacterial drugs.
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10
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