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新型噻唑基氰基丙烯酰胺衍生物：DNA切割、DNA/牛血清白蛋白结合特性及其对结肠癌细胞和乳腺癌细胞的抗癌行为

Novel thiazole-based cyanoacrylamide derivatives: DNA cleavage, DNA/BSA binding properties and their anticancer behaviour against colon and breast cancer cells.

作者信息

Barakat Karim, Ragheb Mohamed A, Soliman Marwa H, Abdelmoniem Amr M, Abdelhamid Ismail A

机构信息

Department of Chemistry (Biochemistry Division), Faculty of Science, Cairo University, Giza, 12613, Egypt.

Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt.

出版信息

BMC Chem. 2024 Sep 20;18(1):183. doi: 10.1186/s13065-024-01284-2.

DOI:10.1186/s13065-024-01284-2
PMID:39304938
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11414077/
Abstract

A novel series of 2-cyano-3-(pyrazol-4-yl)-N-(thiazol-2-yl)acrylamide derivatives (3a-f) were synthesized using Knoevenagel condensation and characterized using various spectral tools. The weak nuclease activity of compounds (3a-f) against pBR322 plasmid DNA was greatly enhanced by irradiation at 365 nm. Compounds 3b and 3c, incorporating thienyl and pyridyl moieties, respectively, exhibited the utmost nuclease activity in degrading pBR322 plasmid DNA through singlet oxygen and superoxide free radicals' species. Furthermore, compounds 3b and 3c affinities towards calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) were investigated using UV-Vis and fluorescence spectroscopic analysis. They revealed good binding characteristics towards CT-DNA with K values of 6.68 × 10 M and 1.19 × 10 M for 3b and 3c, respectively. In addition, compounds 3b and 3c ability to release free radicals on radiation were targeted to be used as cytotoxic compounds in vitro for colon (HCT116) and breast cancer (MDA-MB-231) cells. A significant reduction in the cell viability on illumination at 365 nm was observed, with IC values of 23 and 25 µM against HCT116 cells, and 30 and 9 µM against MDA-MB-231 cells for compounds 3b and 3c, respectively. In conclusion, compounds 3b and 3c exhibited remarkable DNA cleavage and cytotoxic activity on illumination at 365 nm which might be associated with free radicals' production in addition to having a good affinity for interacting with CT-DNA and BSA.

摘要

通过克诺文纳格尔缩合反应合成了一系列新型的2-氰基-3-(吡唑-4-基)-N-(噻唑-2-基)丙烯酰胺衍生物(3a - f)，并使用各种光谱工具对其进行了表征。化合物(3a - f)对pBR322质粒DNA的微弱核酸酶活性在365 nm光照下得到了极大增强。分别含有噻吩基和吡啶基部分的化合物3b和3c，通过单线态氧和超氧自由基在降解pBR322质粒DNA方面表现出最大的核酸酶活性。此外，使用紫外可见光谱和荧光光谱分析研究了化合物3b和3c对小牛胸腺DNA(CT - DNA)和牛血清白蛋白(BSA)的亲和力。结果表明，它们对CT - DNA具有良好的结合特性，化合物3b和3c与CT - DNA的结合常数K值分别为6.68×10⁵ M和1.19×10⁵ M。此外，化合物3b和3c在辐射时释放自由基的能力使其有望作为体外对结肠(HCT116)和乳腺癌(MDA - MB - 231)细胞具有细胞毒性的化合物。在365 nm光照下观察到细胞活力显著降低，化合物3b和3c对HCT116细胞的IC₅₀值分别为23和25 μM，对MDA - MB - 231细胞的IC₅₀值分别为30和9 μM。总之，化合物3b和3c在365 nm光照下表现出显著的DNA切割和细胞毒性活性，这可能与自由基的产生有关，此外它们还对与CT - DNA和BSA相互作用具有良好的亲和力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/c7b8d6b245c7/13065_2024_1284_Fig12_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/6d9575e29c36/13065_2024_1284_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/c7b8d6b245c7/13065_2024_1284_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/99b0b1f44cdd/13065_2024_1284_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/0f29f7ad15c2/13065_2024_1284_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/4e2649d1b534/13065_2024_1284_Fig2_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/edd5877c38d0/13065_2024_1284_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/af2644936cb0/13065_2024_1284_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/6d432f2411b6/13065_2024_1284_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/c514931e2527/13065_2024_1284_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/bc586175b35b/13065_2024_1284_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/098f6623044c/13065_2024_1284_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/8c8c986d75ae/13065_2024_1284_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/6d9575e29c36/13065_2024_1284_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4de4/11414077/c7b8d6b245c7/13065_2024_1284_Fig12_HTML.jpg

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