Platinum N-Heterocyclic Carbene Complexes Based on Adenosine: Synthesis and Antiproliferative Studies.

IF 3.4 4区医学 Q2 CHEMISTRY, MEDICINAL

ChemMedChem Pub Date : 2025-06-04 DOI:10.1002/cmdc.202500368

Giulia Orsini, Andreia Marinho, Claudia Nunes, Ana Petronilho

引用次数: 0

Abstract

Platinum(II) N-heterocyclic carbene complexes based on 2-chloroadenosine are synthesized. The reaction of 2-chloro-2',3',5'-tri-O-acetyladenosine 1 with Pt(PPh₃)₄ by C-Cl oxidative addition yields complex 2, with a Pt^II center bond to the C-2 of the purine ring. Complex 2 reacts with methyl iodide to yield N-heterocyclic carbene 3, which is subsequently deprotected under basic conditions to provide N-heterocyclic carbene 4, bearing a fully deprotected ribose. The compounds are tested for their cytotoxic activity in five different cell lines: L929, HEK293, A375, MDA-MB-231, and MCF-7. Among the platinum compounds, compound 2, the neutral compound bearing an anionic adenosyl ligand, provides the highest cytotoxic activity, particularly against the A375 and MDA-MB-231 cell lines. Encapsulation of compound 2 with nanostructured lipid carriers does not lead to an improvement in the cytotoxic activity.

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基于腺苷的铂n -杂环卡宾配合物：合成及抗增殖研究。

合成了基于2-氯腺苷的铂（II） n -杂环羰基配合物。2-氯-2',3',5'-三- o-乙酰腺苷1与Pt(PPh3)4通过C-Cl氧化加成反应得到配合物2，其PtII中心与嘌呤环的C-2键合。配合物2与碘化甲酯反应生成n -杂环卡宾3，随后在碱性条件下脱保护生成n -杂环卡宾4，携带一个完全脱保护的核糖。在五种不同的细胞系L929、HEK293、A375、MDA-MB-231和MCF-7中测试了这些化合物的细胞毒活性。在铂类化合物中，含有阴离子腺苷配体的中性化合物化合物2具有最高的细胞毒活性，特别是对A375和MDA-MB-231细胞系。用纳米结构脂质载体包封化合物2不会导致细胞毒活性的提高。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ChemMedChem 医学-药学

CiteScore

6.70

自引率

2.90%

发文量

280

审稿时长

1 months

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