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

被引：14

作者：

Barakat, Karim ^{[1
]}

Ragheb, Mohamed A. ^{[1
]}

Soliman, Marwa H. ^{[1
]}

Abdelmoniem, Amr M. ^{[2
]}

Abdelhamid, Ismail A. ^{[2
]}

机构：

[1] Cairo Univ, Fac Sci, Dept Chem, Biochem Div, Giza 12613, Egypt

[2] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt

来源：

BMC CHEMISTRY | 2024年 / 18卷 / 01期

关键词：

Cyanoacrylamide; DNA photocleavage; DNA/BSA binding; Cytotoxicity; HCT116; cells; MDA-MB-231; Photodynamic therapy; MOLECULAR DOCKING; DRUG-DELIVERY; CYTOTOXICITY; ANTIBACTERIAL; COMPLEXES; HYBRIDS;

D O I：

10.1186/s13065-024-01284-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 Kb values of 6.68 x 104 M-1 and 1.19 x 104 M-1 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 IC50 values of 23 and 25 mu M against HCT116 cells, and 30 and 9 mu M 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.

引用

页数：17

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