二茂铁基 β-二酮化合物:用于提高抗癌活性的扩展环系统。

IF 2.6 4区 生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
ChemBioChem Pub Date : 2024-10-24 DOI:10.1002/cbic.202400759
Benjamin J Hofmann, Enas T Aljohani, Natalia Cicovacki, Ivan Lee, Derek T Warren, Anastasia Sobolewski, Tameryn Stringer, Rianne M Lord
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引用次数: 0

摘要

我们合成了一个具有不同芳香族官能度的β-二酮酸二茂铁化合物库,并对其进行了全面表征。其中包括循环伏安法和通过单晶 X 射线衍射分析四种新结构。通过 MTT 筛选,确定了化合物对胰腺癌(MIA PaCa-2)、卵巢腺癌(A2780)、乳腺癌(MDA-MB-231 和 MCF-7)和正常视网膜上皮细胞(ARPE-19)的细胞毒性潜力。这些化合物呈现出一种总体趋势,即分子中芳香环数量的增加会导致细胞毒性的增加,其趋势为蒽基 > 萘基 > 苯基 > 甲基。这些化合物对三阴性癌细胞株 MDA-MB-231 特别敏感,并通过荧光显微镜下活性氧的产生和扫描电子显微镜下的细胞形态研究了其潜在的作用模式。所有检测结果都表明,具有蒽取代基的二茂铁β-二酮酸酯是该化合物库中的主要化合物。共聚焦显微镜还观察到细胞内的分解产生了具有细胞毒性的荧光分子。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Ferrocenyl β-Diketonate Compounds: Extended Ring Systems for Improved Anticancer Activity.

A library of ferrocenyl β-diketonate compounds with varying degrees of aromatic functionality have been synthesized and fully characterized. This includes cyclic voltammetry and the analysis of four new structures by single crystal X-ray diffraction. The compounds cytotoxic potential has been determined by MTT screening against pancreatic carcinoma (MIA PaCa-2), ovarian adenocarcinoma (A2780), breast adenocarcinomas (MDA-MB-231 and MCF-7) and normal epithelial retinal (ARPE-19). The compounds show a general trend, where increasing the number of aromatic rings in the molecule yields an increase in cytotoxicity and follows the trend anthracenyl>naphthyl>phenyl>methyl. The compounds are particularly sensitive to the triple negative cancer cell line MDA-MB-231, and the potential modes of action have been studied by production of reactive oxygen species using fluorescence microscopy and cell morphology using Scanning Electron Microscopy. All assays highlight the ferrocenyl β-diketonate with an anthracenyl substituent to be the lead compound in this library. The decomposition of this compound was also observed within cells, yielding a cytotoxic fluorescent molecule, which has been visualized by confocal microscopy.

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来源期刊
ChemBioChem
ChemBioChem 生物-生化与分子生物学
CiteScore
6.10
自引率
3.10%
发文量
407
审稿时长
1 months
期刊介绍: ChemBioChem (Impact Factor 2018: 2.641) publishes important breakthroughs across all areas at the interface of chemistry and biology, including the fields of chemical biology, bioorganic chemistry, bioinorganic chemistry, synthetic biology, biocatalysis, bionanotechnology, and biomaterials. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and supported by the Asian Chemical Editorial Society (ACES).
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