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设计、合成及新型吲哚二氢吡唑衍生物的体外评价作为潜在的抗癌剂。

Design, Synthesis, and In Vitro Evaluation of Novel Indolyl DiHydropyrazole Derivatives as Potential Anticancer Agents.

机构信息

Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia.

Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa.

出版信息

Molecules. 2021 Aug 29;26(17):5235. doi: 10.3390/molecules26175235.

DOI:10.3390/molecules26175235
PMID:34500672
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8434462/
Abstract

Indoles derived from both natural sources or artificial synthetic methods have been known to interact with aryl hydrocarbon receptors (AhR), and exhibit anticancer activity. In light of these attractive properties, a series of hybrid molecules with structural features of indoles, i.e., those bearing a pyrazoline nucleus, were evaluated for their enhanced anticancer activity. The designed molecules were subjected to molecular docking in order to screen for potential AhR interacting compounds, and the identified indolyl dihydropyrazole derivatives were synthesized. The synthesized compounds were characterized, and their cytotoxicity was evaluated against four human cancer cell lines using the MTT assay. Based on the Glide g-score, H-bonding interactions and bonding energy of 20 candidate molecules were selected for further analysis from the 64 initially designed molecules. These candidate molecules have shown promising anti-proliferative activity against the cell lines tested. Among these candidate molecules, the compounds with hydroxy phenyl substitution on the pyrazoline ring have shown potent activity across all the tested cell lines. The designed scaffold was proven effective for screening potential candidate molecules with anticancer properties, and may be further optimized structurally for yielding the ideal anti-tumorigenic compound for the treatment of various cancers.

摘要

从天然来源或人工合成方法中获得的吲哚衍生物已知与芳烃受体 (AhR) 相互作用,并具有抗癌活性。鉴于这些诱人的特性,一系列具有吲哚结构特征的杂交分子,即含有吡唑啉核的分子,被评估其增强的抗癌活性。设计的分子经过分子对接筛选,以寻找潜在的 AhR 相互作用化合物,并合成了鉴定出的吲哚二氢吡唑衍生物。合成的化合物进行了表征,并通过 MTT 测定法评估了它们对四种人癌细胞系的细胞毒性。根据 Glide g 评分,从最初设计的 64 种分子中选择了 20 种候选分子的氢键相互作用和结合能进行进一步分析。这些候选分子对测试的细胞系表现出有希望的抗增殖活性。在这些候选分子中,吡唑啉环上带有羟基苯基取代的化合物在所有测试的细胞系中均表现出很强的活性。所设计的支架被证明可有效筛选具有抗癌特性的潜在候选分子,并可进一步进行结构优化,以获得用于治疗各种癌症的理想抗肿瘤化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/3a3e9f84e319/molecules-26-05235-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/ec15c7e5cc0a/molecules-26-05235-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/292b1de9dd10/molecules-26-05235-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/9869a2e78e6b/molecules-26-05235-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/9f1483c0f2e1/molecules-26-05235-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/0ed6635b15f7/molecules-26-05235-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/3a3e9f84e319/molecules-26-05235-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/ec15c7e5cc0a/molecules-26-05235-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/292b1de9dd10/molecules-26-05235-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/9869a2e78e6b/molecules-26-05235-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/9f1483c0f2e1/molecules-26-05235-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/0ed6635b15f7/molecules-26-05235-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32bd/8434462/3a3e9f84e319/molecules-26-05235-g006.jpg

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