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Promising Anticancer Prodrugs Based on Pt(IV) Complexes with Bis-organosilane Ligands in Axial Positions

Francisco Navas, Ana Chocarro‐Calvo, Patricia Iglesias-Hernández, Paloma Fernández-García, Victoria Morales, José Manuel García-Martínez, R. Sanz, Antonio De la Vieja, Custodia García‐Jiménez, Rafael A. García‐Muñoz

2024Journal of Medicinal Chemistry17 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide We report two novel prodrug Pt(IV) complexes with bis-organosilane ligands in axial positions: cis -dichloro(diamine)- trans -[3-(triethoxysilyl)propylcarbamate]platinum(IV) (Pt(IV)-biSi-1) and cis -dichloro(diisopropylamine)- trans -[3-(triethoxysilyl) propyl carbamate]platinum(IV) (Pt(IV)-biSi-2). Pt(IV)-biSi-2 demonstrated enhanced in vitro cytotoxicity against colon cancer cells (HCT 116 and HT-29) compared with cisplatin and Pt(IV)-biSi-1. Notably, Pt(IV)-biSi-2 exhibited higher cytotoxicity toward cancer cells and lower toxicity on nontumorigenic intestinal cells (HIEC6). In preclinical mouse models of colorectal cancer, Pt(IV)-biSi-2 outperformed cisplatin in reducing tumor growth at lower concentrations, with reduced side effects. Mechanistically, Pt(IV)-biSi-2 induced permanent DNA damage independent of p53 levels. DNA damage such as double-strand breaks marked by histone gH2Ax was permanent after treatment with Pt(IV)-biSi-2, in contrast to cisplatin's transient effects. Pt(IV)-biSi-2's faster reduction to Pt(II) species upon exposure to biological reductants supports its superior biological response. These findings unveil a novel strategy for designing Pt(IV) anticancer prodrugs with enhanced activity and specificity, offering therapeutic opportunities beyond conventional Pt drugs.

Topics & Concepts

ChemistryProdrugCytotoxicityCisplatinPlatinumCarboxylateIn vitroStereochemistryBiochemistryCatalysisChemotherapyMedicineSurgeryMetal complexes synthesis and propertiesFerrocene Chemistry and ApplicationsLanthanide and Transition Metal Complexes