Karim Barakat, Mohamed A. Ragheb, Marwa H. Soliman, Amr M. Abdelmoniem, Ismail A. Abdelhamid
{"title":"新型噻唑基氰基丙烯酰胺衍生物：DNA 裂解、DNA/BSA 结合特性及其对结肠癌和乳腺癌细胞的抗癌作用","authors":"Karim Barakat, Mohamed A. Ragheb, Marwa H. Soliman, Amr M. Abdelmoniem, Ismail A. Abdelhamid","doi":"10.1186/s13065-024-01284-2","DOIUrl":null,"url":null,"abstract":"<div><p>A novel series of 2-cyano-3-(pyrazol-4-yl)-<i>N</i>-(thiazol-2-yl)acrylamide derivatives (<b>3a</b>–<b>f</b>) were synthesized using Knoevenagel condensation and characterized using various spectral tools. The weak nuclease activity of compounds <b>(3a</b>–<b>f)</b> against pBR322 plasmid DNA was greatly enhanced by irradiation at 365 nm. Compounds <b>3b</b> and <b>3c</b>, 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 <b>3b</b> and <b>3c</b> 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<sub>b</sub> values of 6.68 × 10<sup>4</sup> M<sup>−1</sup> and 1.19 × 10<sup>4</sup> M<sup>−1</sup> for <b>3b</b> and <b>3c</b>, respectively. In addition, compounds <b>3b</b> and <b>3c</b> 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<sub>50</sub> values of 23 and 25 µM against HCT116 cells, and 30 and 9 µM against MDA-MB-231 cells for compounds <b>3b</b> and <b>3c</b>, respectively. In conclusion, compounds <b>3b</b> and <b>3c</b> 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.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":496,"journal":{"name":"BMC Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://bmcchem.biomedcentral.com/counter/pdf/10.1186/s13065-024-01284-2","citationCount":"0","resultStr":"{\"title\":\"Novel thiazole-based cyanoacrylamide derivatives: DNA cleavage, DNA/BSA binding properties and their anticancer behaviour against colon and breast cancer cells\",\"authors\":\"Karim Barakat, Mohamed A. Ragheb, Marwa H. Soliman, Amr M. Abdelmoniem, Ismail A. Abdelhamid\",\"doi\":\"10.1186/s13065-024-01284-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A novel series of 2-cyano-3-(pyrazol-4-yl)-<i>N</i>-(thiazol-2-yl)acrylamide derivatives (<b>3a</b>–<b>f</b>) were synthesized using Knoevenagel condensation and characterized using various spectral tools. The weak nuclease activity of compounds <b>(3a</b>–<b>f)</b> against pBR322 plasmid DNA was greatly enhanced by irradiation at 365 nm. Compounds <b>3b</b> and <b>3c</b>, 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 <b>3b</b> and <b>3c</b> 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<sub>b</sub> values of 6.68 × 10<sup>4</sup> M<sup>−1</sup> and 1.19 × 10<sup>4</sup> M<sup>−1</sup> for <b>3b</b> and <b>3c</b>, respectively. In addition, compounds <b>3b</b> and <b>3c</b> 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<sub>50</sub> values of 23 and 25 µM against HCT116 cells, and 30 and 9 µM against MDA-MB-231 cells for compounds <b>3b</b> and <b>3c</b>, respectively. In conclusion, compounds <b>3b</b> and <b>3c</b> 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.</p><h3>Graphical Abstract</h3>\\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":496,\"journal\":{\"name\":\"BMC Chemistry\",\"volume\":\"18 1\",\"pages\":\"\"},\"PeriodicalIF\":4.3000,\"publicationDate\":\"2024-09-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://bmcchem.biomedcentral.com/counter/pdf/10.1186/s13065-024-01284-2\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"BMC Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1186/s13065-024-01284-2\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"BMC Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1186/s13065-024-01284-2","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Novel thiazole-based cyanoacrylamide derivatives: DNA cleavage, DNA/BSA binding properties and their anticancer behaviour against colon and breast cancer cells
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 × 104 M−1 and 1.19 × 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 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.
期刊介绍：
BMC Chemistry, formerly known as Chemistry Central Journal, is now part of the BMC series journals family.
Chemistry Central Journal has served the chemistry community as a trusted open access resource for more than 10 years – and we are delighted to announce the next step on its journey. In January 2019 the journal has been renamed BMC Chemistry and now strengthens the BMC series footprint in the physical sciences by publishing quality articles and by pushing the boundaries of open chemistry.
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