Understanding the Photodynamic Behavior of Red Emitting Re(I)dipyrrinates in Triple-Negative Breast Cancer Cells

IF 3.9 3区医学 Q2 CHEMISTRY, MEDICINAL

ACS Medicinal Chemistry Letters Pub Date : 2026-08-13 Epub Date: 2026-07-31 DOI:10.1021/acsmedchemlett.6c00168

Neha Manav, Jaydeepsinh Chavda, Dhiraj Bhatia, Iti Gupta

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引用次数: 0

Abstract

The Re(I)dipyrrinates complexes having oligo ethylene glycol (OEG) and thioglucose/thiogalactose sugars at the C-8 position are explored for anticancer applications. The X-ray crystal structure of Re(I)dipyrrinate having a thiogalactose sugar revealed distorted octrahedral geometry of the central metal. The Re(I)dipyrrinates showed red emission (600–900 nm) with noticeably large Stokes shifts (∼5890–6800 cm^–1), a highly desirable property for bioimaging application. The Re(I)dipyrrinates were found to be nontoxic in dark conditions on triple negative breast cancer cells (TNBC), whereas Re(I)dipyrrinate with OEG group and thioglucose sugar displayed excellent phototoxicity in TNBC with IC₅₀ values of 2.6 and 1.5 μM, respectively. The Re(I)dipyrrinate with OEG group displayed preferential colocalization in the lipid droplets and caused lipid peroxidation after light exposure. Additionally, all Re(I)dipyrrinates were nontoxic to the normal retinal pigment epithelial cells (RPE-1) both in the dark and under light irradiation, reflecting suitable behavior as the anticancer agents for photodynamic therapy.

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了解三阴性乳腺癌细胞中红色发射Re(I)二吡啶酸酯的光动力学行为

研究了在C-8位具有低聚乙二醇（OEG）和硫代葡萄糖/硫代半乳糖的Re(I)二吡啶酸酯配合物的抗癌应用。含硫半乳糖的Re(I)二吡啶酯的x射线晶体结构显示中心金属的畸变八面体几何。Re(I)二吡啶酸酯显示出红色发射（600-900nm），具有明显的大Stokes位移（~ 5890-6800cm-1），这是生物成像应用的一个非常理想的特性。Re(I)二吡啶酸酯在黑暗条件下对三阴性乳腺癌细胞（TNBC）无毒，而Re(I)二吡啶酸酯与OEG组和巯基葡萄糖组在TNBC中表现出优异的光毒性，IC50值分别为2.6和1.5 μM。Re(I)双吡啶酸与OEG组在光照射后在脂滴中表现出优先共定位并引起脂质过氧化。此外，所有Re(I)二吡啶酸酯在黑暗和光照下对正常视网膜色素上皮细胞（RPE-1）均无毒性，反映出作为光动力治疗的抗癌药物的合适行为。

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来源期刊

ACS Medicinal Chemistry Letters CHEMISTRY, MEDICINAL-

CiteScore

7.30

自引率

2.40%

发文量

328

审稿时长

1 months

期刊介绍： ACS Medicinal Chemistry Letters is interested in receiving manuscripts that discuss various aspects of medicinal chemistry. The journal will publish studies that pertain to a broad range of subject matter, including compound design and optimization, biological evaluation, drug delivery, imaging agents, and pharmacology of both small and large bioactive molecules. Specific areas include but are not limited to: Identification, synthesis, and optimization of lead biologically active molecules and drugs (small molecules and biologics) Biological characterization of new molecular entities in the context of drug discovery Computational, cheminformatics, and structural studies for the identification or SAR analysis of bioactive molecules, ligands and their targets, etc. Novel and improved methodologies, including radiation biochemistry, with broad application to medicinal chemistry Discovery technologies for biologically active molecules from both synthetic and natural (plant and other) sources Pharmacokinetic/pharmacodynamic studies that address mechanisms underlying drug disposition and response Pharmacogenetic and pharmacogenomic studies used to enhance drug design and the translation of medicinal chemistry into the clinic Mechanistic drug metabolism and regulation of metabolic enzyme gene expression Chemistry patents relevant to the medicinal chemistry field.