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Reaction Behavior of [1,3-Diethyl-4,5-diphenyl-1H-imidazol-2-ylidene] Containing Gold(I/III) Complexes against Ingredients of the Cell Culture Medium and the Meaning on the Potential Use for Cancer Eradication Therapy.
Kapitza, Paul; Scherfler, Amelie; Salcher, Stefan; Sopper, Sieghart; Cziferszky, Monika; Wurst, Klaus; Gust, Ronald.
Afiliación
  • Kapitza P; Department of Pharmaceutical Chemistry, Institute of Pharmacy, Center for Molecular Bioscience Innsbruck, University of Innsbruck, Innrain 80/82, Innsbruck A-6020, Austria.
  • Scherfler A; Department of Pharmaceutical Chemistry, Institute of Pharmacy, Center for Molecular Bioscience Innsbruck, University of Innsbruck, Innrain 80/82, Innsbruck A-6020, Austria.
  • Salcher S; Department of Internal Medicine V, Haematology & Oncology, Medical University Innsbruck, Anichstrasse 35, Innsbruck A-6020, Austria.
  • Sopper S; Department of Internal Medicine V, Haematology & Oncology, Medical University Innsbruck, Anichstrasse 35, Innsbruck A-6020, Austria.
  • Cziferszky M; Department of Pharmaceutical Chemistry, Institute of Pharmacy, Center for Molecular Bioscience Innsbruck, University of Innsbruck, Innrain 80/82, Innsbruck A-6020, Austria.
  • Wurst K; Department of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Innrain 80/82, Innsbruck A-6020, Austria.
  • Gust R; Department of Pharmaceutical Chemistry, Institute of Pharmacy, Center for Molecular Bioscience Innsbruck, University of Innsbruck, Innrain 80/82, Innsbruck A-6020, Austria.
J Med Chem ; 66(12): 8238-8250, 2023 06 22.
Article en En | MEDLINE | ID: mdl-37294951
ABSTRACT
The reactivities of halido[1,3-diethyl-4,5-diphenyl-1H-imidazol-2-ylidene]gold(I) (chlorido (5), bromido (6), iodido (7)), bis[1,3-diethyl-4,5-diphenyl-1H-imidazol-2-ylidene]gold(I) (8), and bis[1,3-diethyl-4,5-diphenyl-1H-imidazol-2-ylidene]dihalidogold(III) (chlorido (9), bromido (10), iodido (11)) complexes against ingredients of the cell culture medium were analyzed by HPLC. The degradation in the RPMI 1640 medium was studied, too. Complex 6 quantitatively reacted with chloride to 5, while 7 showed additionally ligand scrambling to 8. Interactions with non-thiol containing amino acids could not be detected. However, glutathione (GSH) reacted immediately with 5 and 6 yielding the (NHC)gold(I)-GSH complex 12. The most active complex 8 was stable under in vitro conditions and strongly participated on the biological effects of 7. The gold(III) species 9-11 were completely reduced by GSH to 8 and are prodrugs. All complexes were tested for inhibitory effects in Cisplatin-resistant cells, as well as against cancer stem cell-enriched cell lines and showed excellent activity. Such compounds are of utmost interest for the therapy of drug-resistant tumors.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Neoplasias / Antineoplásicos Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Austria

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Neoplasias / Antineoplásicos Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Austria
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