Triazine-Cored BODIPY Trimers: Synthesis, Properties, and Anticancer Activity

IF 3.7 2区化学 Q2 CHEMISTRY, APPLIED Applied Organometallic Chemistry Pub Date : 2024-12-10 DOI:10.1002/aoc.7915

Laxmipriya Nayak, Supriya Routray, Subhadeep Acharya, Anwesha Pradhan, Sajan Sahoo, Luna Samanta, Saiprakash Rout, Rashmirekha Satapathy

{"title":"Triazine-Cored BODIPY Trimers: Synthesis, Properties, and Anticancer Activity","authors":"Laxmipriya Nayak, Supriya Routray, Subhadeep Acharya, Anwesha Pradhan, Sajan Sahoo, Luna Samanta, Saiprakash Rout, Rashmirekha Satapathy","doi":"10.1002/aoc.7915","DOIUrl":null,"url":null,"abstract":"<div>\n \n Two triazine-cored BODIPY trimers (Compounds 6 and 12) were synthesized and well characterized using 1H NMR, 13C NMR, 11B NMR, 19F NMR, FT-IR, and high-resolution mass spectral analysis. The photophysical, computational, and in vitro anticancer studies of the synthesized compounds were comprehensively evaluated along with previously reported phenylene-BODIPY trimer (Compound 1). The photophysical studies indicated that the triazine-cored BODIPY trimers exhibited a slight bathochromic shift compared to the phenylene-cored trimer. Density functional theory (DFT) calculations suggest that the order of stability of the BODIPY trimers was 1 > 6 > 12. The anticancer efficacy of the BODIPY trimers was investigated against human breast adenocarcinomas cell line MDA-MB-231 and mouse embryo fibroblast cell line NIH/3T3 through in vitro cytotoxicity assay. All the BODIPY trimers exhibited elevated cytotoxicity towards cancer cells while displaying lesser cytotoxicity towards normal cells. Compound 6 showed the highest cell death potential with an IC50 value of 27.02 μM, which is twice higher than that of the chemotherapeutic drug cisplatin. The triazine-cored BODIPY trimers demonstrated superior cytotoxicity against cancer cells in comparison to their phenylene-cored counterparts. The enhanced cytotoxicity of the triazine-cored trimers suggests that the triazine core plays a crucial role in enhancing their therapeutic efficacy. This result underscores the potential of triazine-cored BODIPY trimers as promising anticancer agents.\n </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"39 1","pages":""},"PeriodicalIF":3.7000,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Applied Organometallic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/aoc.7915","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

Abstract

Two triazine-cored BODIPY trimers (Compounds 6 and 12) were synthesized and well characterized using ¹H NMR, ¹³C NMR, ¹¹B NMR, ¹⁹F NMR, FT-IR, and high-resolution mass spectral analysis. The photophysical, computational, and in vitro anticancer studies of the synthesized compounds were comprehensively evaluated along with previously reported phenylene-BODIPY trimer (Compound 1). The photophysical studies indicated that the triazine-cored BODIPY trimers exhibited a slight bathochromic shift compared to the phenylene-cored trimer. Density functional theory (DFT) calculations suggest that the order of stability of the BODIPY trimers was 1 > 6 > 12. The anticancer efficacy of the BODIPY trimers was investigated against human breast adenocarcinomas cell line MDA-MB-231 and mouse embryo fibroblast cell line NIH/3T3 through in vitro cytotoxicity assay. All the BODIPY trimers exhibited elevated cytotoxicity towards cancer cells while displaying lesser cytotoxicity towards normal cells. Compound 6 showed the highest cell death potential with an IC₅₀ value of 27.02 μM, which is twice higher than that of the chemotherapeutic drug cisplatin. The triazine-cored BODIPY trimers demonstrated superior cytotoxicity against cancer cells in comparison to their phenylene-cored counterparts. The enhanced cytotoxicity of the triazine-cored trimers suggests that the triazine core plays a crucial role in enhancing their therapeutic efficacy. This result underscores the potential of triazine-cored BODIPY trimers as promising anticancer agents.

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

三嗪芯 BODIPY 三聚体：合成、性质和抗癌活性

合成了两个以三嗪为核心的BODIPY三聚体（化合物6和12），并通过1H NMR、13C NMR、11B NMR、19F NMR、FT-IR和高分辨率质谱分析对其进行了表征。合成化合物的光物理、计算和体外抗癌研究与先前报道的苯-BODIPY三聚体（化合物1）一起进行了全面评估。光物理研究表明，与苯基三聚体相比，三嗪包芯的BODIPY三聚体表现出轻微的色移。密度泛函理论（DFT）计算表明，BODIPY三聚体的稳定阶数为1 >； 6 > 12。通过体外细胞毒实验研究了BODIPY三聚体对人乳腺腺癌细胞系MDA-MB-231和小鼠胚胎成纤维细胞系NIH/3T3的抗癌作用。所有BODIPY三聚体对癌细胞的细胞毒性均升高，而对正常细胞的细胞毒性较低。化合物6显示出最高的细胞死亡电位，IC50值为27.02 μM，是化疗药物顺铂的2倍。以三嗪为核心的BODIPY三聚体与以苯为核心的三聚体相比，对癌细胞表现出优越的细胞毒性。三嗪核三聚体的细胞毒性增强表明三嗪核在提高其治疗效果方面起着至关重要的作用。这一结果强调了以三嗪为核心的BODIPY三聚体作为抗癌药物的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Applied Organometallic Chemistry 化学-无机化学与核化学

CiteScore

7.80

自引率

10.30%

发文量

408

审稿时长

2.2 months

期刊介绍： All new compounds should be satisfactorily identified and proof of their structure given according to generally accepted standards. Structural reports, such as papers exclusively dealing with synthesis and characterization, analytical techniques, or X-ray diffraction studies of metal-organic or organometallic compounds will not be considered. The editors reserve the right to refuse without peer review any manuscript that does not comply with the aims and scope of the journal. Applied Organometallic Chemistry publishes Full Papers, Reviews, Mini Reviews and Communications of scientific research in all areas of organometallic and metal-organic chemistry involving main group metals, transition metals, lanthanides and actinides. All contributions should contain an explicit application of novel compounds, for instance in materials science, nano science, catalysis, chemical vapour deposition, metal-mediated organic synthesis, polymers, bio-organometallics, metallo-therapy, metallo-diagnostics and medicine. Reviews of books covering aspects of the fields of focus are also published.