Exploring the Impact of Phenanthroline-Based Glycoconjugated Ru(II) Polypyridyl Photosensitizers on Metastasis-Related Processes

IF 3.7 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - A European Journal Pub Date : 2025-05-28 DOI:10.1002/chem.202501105

Elena de la Torre-Rubio, María-Selma Arias-Pérez, Lourdes Gude, Tomás Cuenca, Cristina García-Iriepa, Eva Royo

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Abstract

Novel water-soluble, phosphorescent ruthenium(II) polypyridyl-glycoconjugates of general formula [Ru{N-(1,10-phenanthroline)}₂{N-(1,10-phenanthrolin-5-yl)-β-glycopyranosylamine}][Cl]₂ (glycopyranosyl = D-glucopyranosyl (1), D-mannopyranosyl (2), L-rhamnopyranosyl (3), L-xylopyranosyl (4), and 2,3,4-tri-O-acetyl-L-xylopyranosyl (5)) and corresponding aglycone [Ru{N-(1,10-phenanthroline)}₂{N-(1,10-phenanthrolin-5-amine)}][Cl]₂ (6) have been synthesized and fully characterized. Their stability and behavior in physiological media have been assessed using ultraviolet visible spectroscopy (UV-Vis) and ¹H nuclear magnetic resonance (¹H-NMR), revealing minor N-glycosidic cleavage and high photostability. The photocytotoxicity of the complexes has been evaluated in two different cancer (PC-3 and MCF-7) and one nontumorigenic (HFF-1) cell lines. While exhibiting no toxicity in the dark, some glycoconjugates achieve photoselectivity indexes of up to 40 upon blue-light irradiation. Remarkably, complexes 1–6 potently affect the metastatic phenotype of PC-3 cells, evidenced by the inhibition of migration in the wound healing assay and the increased resistance to trypsin detachment following photoactivation.

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探讨以菲罗啉为基础的糖缀合Ru（II）多吡啶基光敏剂对转移相关过程的影响。

合成了一种新型水溶性磷发光钌（II）多吡啶基糖缀合物，其通式为[Ru{N-（1,10-菲罗啉）}2{N-（1,10-菲罗啉-5-基）-β-glycopyranosylamine}][Cl]2 (glycopyranosyl = D-glucopyranosyl (1)， d -甘露吡喃(2)，l-鼠李糖吡喃(3),L-xylopyranosyl（4)和2,3,4-三- o -乙酰基-L-xylopyranosyl(5)）和相应的苷元[Ru{N-（1,10-菲罗啉）}2{N-（1,10-菲罗啉-5-胺）}][Cl]2(6))，并进行了表征。它们在生理介质中的稳定性和行为已经通过UV-Vis和¹H-NMR进行了评估，显示出少量的n -糖苷切割和高的光稳定性。在两种不同的癌症细胞系（PC-3和MCF-7）和一种非致瘤性细胞系（HFF-1）中评估了这些复合物的光细胞毒性。虽然在黑暗中没有毒性，但一些糖缀合物在蓝光照射下达到高达40的光选择性指数。值得注意的是，复合物1-6可以有效地影响PC-3细胞的转移表型，这可以通过伤口愈合实验中的迁移抑制和光激活后对胰蛋白酶脱落的抵抗力增加来证明。

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来源期刊

Chemistry - A European Journal 化学-化学综合

CiteScore

7.90

自引率

4.70%

发文量

1808

审稿时长

1.8 months

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