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用于抗癌活性的三唑取代喹唑啉杂化物的合成以及作为表皮生长因子受体阻断剂和活性氧诱导剂的先导化合物

Synthesis of Triazole-Substituted Quinazoline Hybrids for Anticancer Activity and a Lead Compound as the EGFR Blocker and ROS Inducer Agent.

作者信息

Banerji Biswadip, Chandrasekhar Kadaiahgari, Sreenath Kancham, Roy Saheli, Nag Sayoni, Saha Krishna Das

机构信息

Organic & Medicinal Chemistry Division, Academy of Scientific and Innovative Research (AcSIR), and Cancer Biology & Inflammatory Disorder, Indian Institute of Chemical Biology (CSIR-IICB), 4 Raja S. C. Mullick Road, Kolkata 700032, India.

National Institute of Pharmaceutical Education and Research (NIPER)-Kolkata, 4, Raja S. C. Mullick Road, Kolkata 700032, India.

出版信息

ACS Omega. 2018 Nov 30;3(11):16134-16142. doi: 10.1021/acsomega.8b01960. Epub 2018 Nov 28.

DOI:10.1021/acsomega.8b01960
PMID:30556027
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6288807/
Abstract

A series of triazole-substituted quinazoline hybrid compounds were designed and synthesized for anticancer activity targeting epidermal growth factor receptor (EGFR) tyrosine kinase. Most of the compounds showed moderate to good antiproliferative activity against four cancer cell lines (HepG2, HCT116, MCF-7, and PC-3). Compound showed good antiproliferative activity (IC = 20.71 μM) against MCF-7 cell lines. Molecular docking results showed that compound formed hydrogen bond with Met 769 and Lys 721 and π-sulfur interaction with Met 742 of EGFR tyrosine kinase (PDB ID: 1M17). Compound decreases the expression of EGFR and p-EGFR. It also induces apoptosis through reactive oxygen species generation, followed by the change in mitochondrial membrane potential.

摘要

设计并合成了一系列三唑取代的喹唑啉杂化化合物，用于靶向表皮生长因子受体（EGFR）酪氨酸激酶的抗癌活性研究。大多数化合物对四种癌细胞系（HepG2、HCT116、MCF-7和PC-3）表现出中度至良好的抗增殖活性。化合物对MCF-7细胞系表现出良好的抗增殖活性（IC = 20.71 μM）。分子对接结果表明，化合物与EGFR酪氨酸激酶的Met 769和Lys 721形成氢键，并与Met 742形成π-硫相互作用（PDB ID：1M17）。化合物降低了EGFR和p-EGFR的表达。它还通过产生活性氧诱导细胞凋亡，随后线粒体膜电位发生变化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c28/6646573/0ca4bc23fd9b/ao-2018-01960v_0005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c28/6646573/60f9a349cfec/ao-2018-01960v_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c28/6646573/0df08164d499/ao-2018-01960v_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c28/6646573/f24a645207bb/ao-2018-01960v_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c28/6646573/233816dd50e1/ao-2018-01960v_0003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c28/6646573/0ca4bc23fd9b/ao-2018-01960v_0005.jpg

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