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靶向三阴性和非三阴性乳腺癌的 -(3-羟基吲哚)- 附加 β-咔啉/四氢-β-咔啉的设计、合成、抗增殖评估及分子对接研究

Design, Synthesis, Antiproliferative Evaluation, and Molecular Docking Studies of -(3-Hydroxyindole)-Appended β-Carbolines/Tetrahydro-β-Carbolines Targeting Triple-Negative and Non-Triple-Negative Breast Cancer.

作者信息

Sharma Bharvi, Saha Sourav Taru, Perumal Shanen, Gu Liang, Ebenezer Oluwakemi, Singh Parvesh, Kaur Mandeep, Kumar Vipan

机构信息

Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India.

School of Molecular and Cell Biology, University of the Witwatersrand, Private Bag 3, WITS, Johannesburg 2050, South Africa.

出版信息

ACS Omega. 2020 Nov 5;5(45):28907-28917. doi: 10.1021/acsomega.0c01226. eCollection 2020 Nov 17.

DOI:10.1021/acsomega.0c01226
PMID:33225121
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7675558/
Abstract

The present manuscript pertains to the design and synthesis of a series of 3-hydroxyindole-substituted β-carbolines/tetrahydro-β-carbolines with an aim to explore their antiproliferative structure-activity relationship against breast cancer. The conjugate with an optimum combination of a flexible tetrahydro-β-carboline core, a tertiary alcoholic group along with a chloro substituent on the indole ring, proved to be the most active compound. It displayed IC values of 13.61 and 22.76 μM against MCF-7 (ER+) and MDA-MB-231 (ER-) cells, respectively. The docking studies were found to be consistent with experimental results owing to the stronger binding affinity of the synthesized conjugates via hydrophobic and H-bonding interactions.

摘要

本手稿涉及一系列3-羟基吲哚取代的β-咔啉/四氢-β-咔啉的设计与合成，旨在探索它们对乳腺癌的抗增殖构效关系。具有柔性四氢-β-咔啉核心、叔醇基团以及吲哚环上氯取代基的最佳组合的共轭物被证明是最具活性的化合物。它对MCF-7（ER+）和MDA-MB-231（ER-）细胞的IC值分别为13.61和22.76 μM。由于合成的共轭物通过疏水和氢键相互作用具有更强的结合亲和力，对接研究结果与实验结果一致。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/8075c2bb2edb/ao0c01226_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/e69c7df0c2b2/ao0c01226_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/44a8c5c4f717/ao0c01226_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/cc1a0ae46f8c/ao0c01226_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/70727a9a2973/ao0c01226_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/24707d5f0927/ao0c01226_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/7996cd33c6de/ao0c01226_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/bef4ed0835e4/ao0c01226_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/d9ae9b85b5e4/ao0c01226_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/8075c2bb2edb/ao0c01226_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/e69c7df0c2b2/ao0c01226_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/44a8c5c4f717/ao0c01226_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/cc1a0ae46f8c/ao0c01226_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/70727a9a2973/ao0c01226_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/24707d5f0927/ao0c01226_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/7996cd33c6de/ao0c01226_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/bef4ed0835e4/ao0c01226_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/d9ae9b85b5e4/ao0c01226_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/039e/7675558/8075c2bb2edb/ao0c01226_0004.jpg

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