• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

新型细胞毒性菲并三嗪-3-硫醇衍生物作为潜在的DNA嵌入剂和Bcl-2抑制剂

Novel Cytotoxic Phenanthro-triazine-3-thiol Derivatives as Potential DNA Intercalators and Bcl-2 Inhibitors.

作者信息

Khoshneviszadeh Mehdi, Firuzi Omidreza, Aminsafaee Malihe, Kashefizadeh Masoud, Ranjbar Sara, Rezaei Zahra, Sadeghpour Hossein, Zargari Farshid, Miri Ramin, Edraki Najmeh

机构信息

Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.

Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.

出版信息

Iran J Pharm Res. 2021 Summer;20(3):161-177. doi: 10.22037/ijpr.2020.113902.14553.

DOI:10.22037/ijpr.2020.113902.14553
PMID:34903979
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8653664/
Abstract

Novel phenanthro-triazine-3-thiol derivatives were designed as potential DNA intercalators and Bcl-2 inhibitors. After being synthesized, the compounds were evaluated for their cytotoxic activity against MOLT-4 (human acute lymphoblastic leukemia) and MCF-7 (human breast adenocarcinoma) cells by MTT assay. (bearing hydrogen substitution) was the most potent derivative against MOLT-4 with an IC value of 7.1 ± 1.1 μM, whereas (bearing phenyl substitution) demonstrated considerable cytotoxicity against MCF-7 with an IC value of 15.4 ± 2.9 μM. Compounds , , and exhibited moderate cytotoxic effects. Furthermore, to confirm the potential DNA intercalation and Bcl-2 inhibitory activities of phenanthro-triazine scaffolds, molecular docking analysis was performed. Molecular docking studies indicated that these compounds not only bind to DNA by intercalation mainly through stacking interactions but also are well accommodated in the active site of Bcl-2. Therefore, and having phenanthro-triazine-3-thiol scaffold could be presented as cytotoxic agents with dual DNA intercalation and Bcl-2 inhibitory activities.

摘要

新型菲咯并三嗪-3-硫醇衍生物被设计为潜在的DNA嵌入剂和Bcl-2抑制剂。合成后，通过MTT法评估这些化合物对MOLT-4（人急性淋巴细胞白血病）和MCF-7（人乳腺腺癌）细胞的细胞毒性活性。（带有氢取代基）是对MOLT-4最有效的衍生物，IC值为7.1±1.1μM，而（带有苯基取代基）对MCF-7表现出相当大的细胞毒性，IC值为15.4±2.9μM。化合物、、和表现出中等的细胞毒性作用。此外，为了证实菲咯并三嗪支架的潜在DNA嵌入和Bcl-2抑制活性，进行了分子对接分析。分子对接研究表明，这些化合物不仅主要通过堆积相互作用以嵌入方式与DNA结合，而且在Bcl-2的活性位点也能很好地容纳。因此，具有菲咯并三嗪-3-硫醇支架的和可作为具有双重DNA嵌入和Bcl-2抑制活性的细胞毒性剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/1b4e61dea597/ijpr-20-161-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/aeece57f114e/ijpr-20-161-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/f73aebcfb34d/ijpr-20-161-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/bb2464712654/ijpr-20-161-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/1ce22f02f4ec/ijpr-20-161-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/9c391afa120f/ijpr-20-161-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/0035e397adc7/ijpr-20-161-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/bc998137e13b/ijpr-20-161-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/419fa122a2a0/ijpr-20-161-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/c98621d72b57/ijpr-20-161-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/918fa182924d/ijpr-20-161-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/ef4cbcd62606/ijpr-20-161-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/1b4e61dea597/ijpr-20-161-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/aeece57f114e/ijpr-20-161-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/f73aebcfb34d/ijpr-20-161-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/bb2464712654/ijpr-20-161-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/1ce22f02f4ec/ijpr-20-161-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/9c391afa120f/ijpr-20-161-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/0035e397adc7/ijpr-20-161-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/bc998137e13b/ijpr-20-161-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/419fa122a2a0/ijpr-20-161-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/c98621d72b57/ijpr-20-161-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/918fa182924d/ijpr-20-161-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/ef4cbcd62606/ijpr-20-161-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2db6/8653664/1b4e61dea597/ijpr-20-161-g012.jpg

相似文献

1
Novel Cytotoxic Phenanthro-triazine-3-thiol Derivatives as Potential DNA Intercalators and Bcl-2 Inhibitors.新型细胞毒性菲并三嗪-3-硫醇衍生物作为潜在的DNA嵌入剂和Bcl-2抑制剂
Iran J Pharm Res. 2021 Summer;20(3):161-177. doi: 10.22037/ijpr.2020.113902.14553.
2
Design, synthesis, molecular docking and anti-proliferative evaluations of [1,2,4]triazolo[4,3-a]quinoxaline derivatives as DNA intercalators and Topoisomerase II inhibitors.设计、合成、分子对接及[1,2,4]三唑并[4,3-a]喹喔啉衍生物作为 DNA 嵌入剂和拓扑异构酶 II 抑制剂的抗增殖活性评价。
Bioorg Chem. 2020 Dec;105:104399. doi: 10.1016/j.bioorg.2020.104399. Epub 2020 Oct 21.
3
Design, synthesis, cytotoxicity evaluation and docking studies of 1,2,4-triazine derivatives bearing different arylidene-hydrazinyl moieties as potential mTOR inhibitors.作为潜在的mTOR抑制剂的带有不同亚芳基肼基部分的1,2,4-三嗪衍生物的设计、合成、细胞毒性评估及对接研究
Res Pharm Sci. 2018 Feb;13(1):1-11. doi: 10.4103/1735-5362.220962.
4
Novel 9-(alkylthio)-Acenaphtho[1,2-e]-1,2,4-triazine derivatives: synthesis, cytotoxic activity and molecular docking studies on B-cell lymphoma 2 (Bcl-2).新型 9-(烷基硫基)-吖[1,2-e]-1,2,4-三嗪衍生物的合成、细胞毒性活性及对 B 细胞淋巴瘤 2 (Bcl-2) 的分子对接研究。
Daru. 2014 Jan 6;22(1):2. doi: 10.1186/2008-2231-22-2.
5
Design, Synthesis, In Vitro Anti-cancer Activity, ADMET Profile and Molecular Docking of Novel Triazolo[3,4-a]phthalazine Derivatives Targeting VEGFR-2 Enzyme.靶向VEGFR-2酶的新型三唑并[3,4-a]酞嗪衍生物的设计、合成、体外抗癌活性、ADMET特性及分子对接
Anticancer Agents Med Chem. 2018;18(8):1184-1196. doi: 10.2174/1871520618666180412123833.
6
Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity.新型 1,3,5-三嗪腙衍生物的合成与表征及其具有良好的抗增殖活性。
Molecules. 2020 Jun 11;25(11):2708. doi: 10.3390/molecules25112708.
7
Discovery and antiproliferative evaluation of new quinoxalines as potential DNA intercalators and topoisomerase II inhibitors.发现并评价新型喹喔啉类化合物作为潜在 DNA 插入剂和拓扑异构酶 II 抑制剂的抗增殖活性。
Arch Pharm (Weinheim). 2019 Nov;352(11):e1900123. doi: 10.1002/ardp.201900123. Epub 2019 Aug 29.
8
Design, synthesis, molecular modeling, in vivo studies and anticancer activity evaluation of new phthalazine derivatives as potential DNA intercalators and topoisomerase II inhibitors.新型酞嗪衍生物作为潜在 DNA 嵌入剂和拓扑异构酶 II 抑制剂的设计、合成、分子模拟、体内研究和抗癌活性评价。
Bioorg Chem. 2020 Oct;103:104233. doi: 10.1016/j.bioorg.2020.104233. Epub 2020 Aug 26.
9
Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors.新型三嗪 - 三唑衍生物作为潜在α - 葡萄糖苷酶抑制剂的合成、体外评价及分子对接研究
Eur J Med Chem. 2017 Jan 5;125:423-429. doi: 10.1016/j.ejmech.2016.09.067. Epub 2016 Sep 21.
10
Discovery of novel triazolophthalazine derivatives as DNA intercalators and topoisomerase II inhibitors.发现新型三唑并酞嗪衍生物作为 DNA 嵌入剂和拓扑异构酶 II 抑制剂。
Arch Pharm (Weinheim). 2021 Jun;354(6):e2000456. doi: 10.1002/ardp.202000456. Epub 2021 Feb 8.

引用本文的文献

1
Design, synthesis, biological evaluation, and studies of novel -substituted-2-(3,4,5-trimethoxyphenyl)-1-benzo[]imidazole-6-carboxamides as promising anticancer agents.新型N-取代-2-(3,4,5-三甲氧基苯基)-1-苯并咪唑-6-甲酰胺作为有前景的抗癌药物的设计、合成、生物学评价及研究
RSC Adv. 2024 Nov 5;14(48):35323-35335. doi: 10.1039/d4ra04492d. eCollection 2024 Nov 4.
2
Design and synthesis of chromene-1,2,3-triazole benzene sulfonamide hybrids as potent carbonic anhydrase-IX inhibitors against prostate cancer.苯并二氢吡喃-1,2,3-三唑苯磺酰胺杂化物作为有效的碳酸酐酶IX抑制剂抗前列腺癌的设计与合成
RSC Med Chem. 2024 Jun 24;15(7):2440-2461. doi: 10.1039/d4md00302k. eCollection 2024 Jul 17.
3

本文引用的文献

1
Acetone Fraction of the Red Marine Alga Reduces the Expression of Bcl-2 Anti-apoptotic Marker and Flotillin-2 Lipid Raft Marker in MCF-7 Breast Cancer Cells.红色海藻的丙酮提取物降低MCF-7乳腺癌细胞中Bcl-2抗凋亡标志物和Flotillin-2脂筏标志物的表达。
Iran J Pharm Res. 2020 Winter;19(1):321-330. doi: 10.22037/ijpr.2020.1100933.
2
Design, synthesis, cytotoxicity evaluation and docking studies of 1,2,4-triazine derivatives bearing different arylidene-hydrazinyl moieties as potential mTOR inhibitors.作为潜在的mTOR抑制剂的带有不同亚芳基肼基部分的1,2,4-三嗪衍生物的设计、合成、细胞毒性评估及对接研究
Res Pharm Sci. 2018 Feb;13(1):1-11. doi: 10.4103/1735-5362.220962.
3
5-Oxo-dihydropyranopyran derivatives as anti-proliferative agents; synthesis, biological evaluation, molecular docking, MD simulation, DFT, and pharmacokinetic studies.
5-氧代二氢吡喃并吡喃衍生物作为抗增殖剂；合成、生物学评价、分子对接、分子动力学模拟、密度泛函理论及药代动力学研究
Heliyon. 2024 Apr 23;10(9):e29850. doi: 10.1016/j.heliyon.2024.e29850. eCollection 2024 May 15.
4
Anticancer evaluation and molecular docking of new pyridopyrazolo-triazine and pyridopyrazolo-triazole derivatives.新型吡啶并吡唑三嗪和吡啶并吡唑三唑衍生物的抗癌评价及分子对接。
Sci Rep. 2023 Feb 16;13(1):2782. doi: 10.1038/s41598-023-29908-y.
BCL2: A promising cancer therapeutic target.
BCL2：一种有前途的癌症治疗靶点。
Biochim Biophys Acta Rev Cancer. 2017 Aug;1868(1):309-314. doi: 10.1016/j.bbcan.2017.06.004. Epub 2017 Jun 21.
4
From basic apoptosis discoveries to advanced selective BCL-2 family inhibitors.从基础的细胞凋亡发现到先进的选择性 BCL-2 家族抑制剂。
Nat Rev Drug Discov. 2017 Apr;16(4):273-284. doi: 10.1038/nrd.2016.253. Epub 2017 Feb 17.
5
Thirty years of BCL-2: translating cell death discoveries into novel cancer therapies.BCL-2 三十年：将细胞死亡发现转化为新型癌症疗法。
Nat Rev Cancer. 2016 Feb;16(2):99-109. doi: 10.1038/nrc.2015.17.
6
Bcl-2 family proteins as regulators of cancer cell invasion and metastasis: a review focusing on mitochondrial respiration and reactive oxygen species.Bcl-2家族蛋白作为癌细胞侵袭和转移的调节因子：一篇聚焦于线粒体呼吸和活性氧的综述
Oncotarget. 2016 Feb 2;7(5):5193-203. doi: 10.18632/oncotarget.6405.
7
Synthetic approaches for sulfur derivatives containing 1,2,4-triazine moiety: their activity for in vitro screening towards two human cancer cell lines.含1,2,4-三嗪部分的硫衍生物的合成方法：它们对两种人类癌细胞系的体外筛选活性。
Chem Pharm Bull (Tokyo). 2015;63(7):531-7. doi: 10.1248/cpb.c15-00153.
8
In vitro antitumor activity evaluation of some 1,2,4-triazine derivatives bearing piperazine amide moiety against breast cancer cells.一些含哌嗪酰胺基团的1,2,4-三嗪衍生物对乳腺癌细胞的体外抗肿瘤活性评价
Bioorg Med Chem. 2014 Nov 15;22(22):6313-23. doi: 10.1016/j.bmc.2014.10.002. Epub 2014 Oct 13.
9
Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling.作为DNA嵌入剂的小分子有机化合物的最新进展：合成、活性及模型构建
Eur J Med Chem. 2014 Mar 3;74:95-115. doi: 10.1016/j.ejmech.2013.11.029. Epub 2014 Jan 3.
10
Novel 9-(alkylthio)-Acenaphtho[1,2-e]-1,2,4-triazine derivatives: synthesis, cytotoxic activity and molecular docking studies on B-cell lymphoma 2 (Bcl-2).新型 9-(烷基硫基)-吖[1,2-e]-1,2,4-三嗪衍生物的合成、细胞毒性活性及对 B 细胞淋巴瘤 2 (Bcl-2) 的分子对接研究。
Daru. 2014 Jan 6;22(1):2. doi: 10.1186/2008-2231-22-2.