新型碳硼烷-硼二吡咯亚甲基共轭物：设计、合成及抗癌活性

Novel carboranyl-BODIPY conjugates: design, synthesis and anti-cancer activity.

作者信息

Mahanta Chandra Sekhara, Hansdah Sunitee, Khuntia Kabita, Jena Bibhuti Bhusan, Swain Biswa Ranjan, Acharya Subhadeep, Dash Barada Prasanna, Debata Priya Ranjan, Satapathy Rashmirekha

机构信息

Department of Chemistry Ravenshaw University College Square Cuttack 753003 Odisha India

Department of Zoology Maharaja Sriram Chandra Bhanja Deo University Sri Ram Chandra Vihar, Takatpur, Mayurbhanj Baripada 757003 Odisha India

出版信息

RSC Adv. 2024 Oct 29;14(47):34643-34660. doi: 10.1039/d4ra07241c.

DOI:10.1039/d4ra07241c

PMID:39479484

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11521004/

Abstract

A series of four carboranyl-BODIPY conjugates (-CB-10, -CB-15, Me--CB-28, and Me--CB-35) and one phenylene-BODIPY conjugate (PB-20) were synthesized. The carboranyl-BODIPY conjugates incorporate boron clusters, specifically - and -carboranes, covalently linked to BODIPY fluorophores while the phenylene-BODIPY conjugate features a phenylene ring covalently linked to BODIPY fluorophore. The newly synthesized conjugates were characterized by H NMR, C NMR, B NMR, F NMR, FT-IR, and high-resolution mass spectral analysis. cytotoxicity of the synthesized conjugates has been evaluated against the HeLa cervical cancer cell line. The study reveals that -CB-10 shows a maximum cell death potential at lower concentrations (12.03 μM) and inhibited cell proliferation and migration in cancer (HeLa) cells. Additionally, flow cytometry study reveals that -CB-10 and Me--CB-28 arrest the cell cycle at the S phase. The results indicate that the carboranyl-BODIPY conjugates have the potential to be effective anticancer agents.

摘要

合成了一系列四种碳硼烷基-硼二吡咯甲川共轭物（-CB-10、-CB-15、甲基--CB-28和甲基--CB-35）以及一种亚苯基-硼二吡咯甲川共轭物（PB-20）。碳硼烷基-硼二吡咯甲川共轭物包含硼簇，特别是-和-碳硼烷，它们与硼二吡咯甲川荧光团共价连接，而亚苯基-硼二吡咯甲川共轭物的特征是一个亚苯基环与硼二吡咯甲川荧光团共价连接。通过氢核磁共振、碳核磁共振、硼核磁共振、氟核磁共振、傅里叶变换红外光谱和高分辨率质谱分析对新合成的共轭物进行了表征。已针对HeLa宫颈癌细胞系评估了合成共轭物的细胞毒性。研究表明，-CB-10在较低浓度（12.03μM）时显示出最大的细胞死亡潜力，并抑制了癌症（HeLa）细胞的增殖和迁移。此外，流式细胞术研究表明，-CB-10和甲基--CB-28使细胞周期停滞在S期。结果表明，碳硼烷基-硼二吡咯甲川共轭物有可能成为有效的抗癌剂。