Bioactive and luminescent indole and isatin based gold(i) derivatives

Fernández-Moreira, V. ; Val-Campillo, C. ; Ospino, I. ; Herrera, R.P. ; Marzo, I. (Universidad de Zaragoza) ; Laguna, A. ; Gimeno, M.C.

Resumen: A series of luminescent monometallic [AuL(PPh 3 )] (1-3) and bimetallic [Au 2 (µ-dppe)L 2 ] (4, 6, 8) and [Au 2 (µ-dppp)L 2 ] (5, 7, 9) complexes, where L is either 4-cyano-indole, isatin, or 5, 7-dimethyl-isatin, and dppe and dppp are 1, 2-bis(diphenylphosphino)ethane and 1, 3-bis(diphenylphosphino)propane, respectively, have been synthesised. X-ray diffraction confirmed the tendency to establish aurophillic interations for those complexes containing dppe. Luminescence studies and theoretical calculations revealed a different origin for both families, i.e. indole and isatin species. Thus, indole derivatives presented a ligand-to-ligand-charge-transfer transition (LLCT) from the indole to the PPh 3 fragment, whereas for the isatin derivatives an intraligand-charge-transfer transition (ILCT) within the isatin fragment is proposed. In both cases, the gold centre was slightly implicated as a ligand-to-metal-charge transfer transition (LMCT) (from the indole/isatin to Au(i)). Cell antiproliferative assays in lung cancer cells (A549), leukemia Jurkat-pLVTHM and Jurkat-shBak cells (cisplatin sensitive and resistant, respectively) showed excellent cytotoxic values (10.11-0.28 µM), showing the leukemia cells to be the most sensitive and the bimetallic species to be the most active agents. Preliminary studies associated the cytotoxicity with a combination of different factors, the metallic fragment being mainly responsible. Remarkably, these complexes are able to inhibit the cellular growth of cisplatin resistant Jurkat-shBak cells highlighting their promising future as an alternative anticancer agent.

Idioma: Inglés

DOI: 10.1039/c8dt00298c

Año: 2019

Publicado en: Dalton Transactions 48, 9 (2019), 3098-3108
ISSN: 1477-9226

Factor impacto JCR: 4.174 (2019)

Categ. JCR: CHEMISTRY, INORGANIC & NUCLEAR rank: 5 / 45 = 0.111 (2019) - Q1 - T1

Factor impacto SCIMAGO: 1.048 - Inorganic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-75816-C2-1-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2017-88091-P

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Biología Celular (Dpto. Bioq.Biolog.Mol. Celular)