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发光双（苯并[]噻唑基）喹喔啉：简便合成、核酸与蛋白质牛血清白蛋白相互作用、活细胞成像、生物制药研究及癌症诊疗应用

Luminescent bis(benzo[]thiazolyl)quinoxaline: facile synthesis, nucleic acid and protein BSA interaction, live-cell imaging, biopharmaceutical research and cancer theranostic application.

作者信息

Babu Lavanya Thilak, Jadhav Gajanan Raosaheb, Paira Priyankar

机构信息

Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology Vellore-632014 Tamilnadu India

Drug Metabolism and Pharmacokinetics, Eurofins Advinus Ltd. 21 & 22, Phase II, Peenya Industrial Area Bangalore 560058 India.

出版信息

RSC Adv. 2019 Mar 18;9(16):8748-8752. doi: 10.1039/c9ra01498e. eCollection 2019 Mar 15.

DOI:10.1039/c9ra01498e
PMID:35517674
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9061853/
Abstract

A series of quinoxaline-2-hydroxyphenylbenzothiazole scaffolds were synthesized and characterized using NMR, UV, fluorescence spectroscopy and LCMS. These newly synthesized compounds were found to be cytotoxic in human epithelioid cervix carcinoma (HeLa) and human colon cancer cell lines (Caco-2). Selectivity of the compounds 7e and 7g are more than 9 fold higher in Caco-2 cells with respect to the normal cell line HEK-293. The most fluorescent compound 7e has displayed high cytoselectivity, significant cellular uptake in HeLa cells and strong binding efficacy with DNA and BSA. The most potent compound 7g has primarily classified as BCS class 4 and BDDCS class 4.

摘要

合成了一系列喹喔啉-2-羟基苯基苯并噻唑支架，并通过核磁共振（NMR）、紫外（UV）、荧光光谱和液相色谱-质谱联用（LCMS）对其进行了表征。发现这些新合成的化合物对人上皮样子宫颈癌（HeLa）细胞系和人结肠癌细胞系（Caco-2）具有细胞毒性。化合物7e和7g在Caco-2细胞中的选择性相对于正常细胞系HEK-293高出9倍以上。荧光最强的化合物7e表现出高细胞选择性、在HeLa细胞中有显著的细胞摄取以及与DNA和牛血清白蛋白（BSA）有强结合效力。最有效的化合物7g主要归类为生物药剂学分类系统（BCS）4类和生物药物处置分类系统（BDDCS）4类。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/b342b8c841b8/c9ra01498e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/2d0a4b386051/c9ra01498e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/624908e6dbab/c9ra01498e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/36202b6a8924/c9ra01498e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/b342b8c841b8/c9ra01498e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/2d0a4b386051/c9ra01498e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/624908e6dbab/c9ra01498e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/36202b6a8924/c9ra01498e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/973b/9061853/b342b8c841b8/c9ra01498e-f3.jpg

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本文引用的文献

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Discovery of benzothiazolylquinoline conjugates as novel human A receptor antagonists: biological evaluations and molecular docking studies.发现苯并噻唑基喹啉缀合物作为新型人类A受体拮抗剂：生物学评价和分子对接研究。
R Soc Open Sci. 2018 Feb 7;5(2):171622. doi: 10.1098/rsos.171622. eCollection 2018 Feb.
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A HO-Responsive Theranostic Probe for Endothelial Injury Imaging and Protection.一种针对内皮损伤的成像和保护的 HO-响应治疗探针。
Theranostics. 2017 Aug 23;7(15):3803-3813. doi: 10.7150/thno.21068. eCollection 2017.
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Mechanisms of Antibacterial Action of Quinoxaline 1,4-di--oxides against and .
喹喔啉 1,4 - 二氧化物对[具体细菌名称未给出]和[具体细菌名称未给出]的抗菌作用机制
Front Microbiol. 2016 Dec 5;7:1948. doi: 10.3389/fmicb.2016.01948. eCollection 2016.
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Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress.基于喹喔啉的埃博拉病毒和马尔堡病毒VP40出芽抑制剂。
Bioorg Med Chem Lett. 2016 Aug 1;26(15):3429-35. doi: 10.1016/j.bmcl.2016.06.053. Epub 2016 Jun 23.
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New imidazoquinoxaline derivatives: Synthesis, biological evaluation on melanoma, effect on tubulin polymerization and structure-activity relationships.新型咪唑并喹喔啉衍生物：合成、对黑色素瘤的生物学评价、对微管蛋白聚合的影响及构效关系
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