2024-03-29T13:37:25Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/50412023-02-07T09:03:01Zcom_10259_4363com_10259_5086com_10259_2604com_10259_4365col_10259_4364col_10259_4366
Strong influence of the ancillary ligand over the photodynamic anticancer properties of neutral biscyclometalated IrIII complexes bearing 2‐benzoazole‐phenolates
Martínez Alonso, Marta
Busto Vázquez, Natalia
Aguirre, Larry Danilo
Berlanga, Leticia
Carrión, María C. .
Cuevas Vicario, José Vicente
Rodríguez, Ana M. .
Carbayo Martín, Mª Aránzazu
Manzano, Blanca R. .
Ortí, Enrique .
Jalón, Félix A.
García Ruiz, Begoña
Espino Ordóñez, Gustavo
2-arylazoles
anticancercomplexes
heterolepticneutraliridium(III)complexes
phosphorescent complexes
photodynamictherapy
In this paper, the synthesis, comprehensive characterization and biological and photocatalytic properties of two series of neutral IrIII biscyclometalated complexes of general formula [Ir(C^N)2(N^O)], where the N^O ligands are 2‐(benzimidazolyl)phenolate‐N,O (L1, series a) and 2‐(benzothiazolyl)phenolate‐N,O (L2, series b), and the C^N ligands are 2‐(phenyl)pyridinate or its derivatives, are described,. Complexes of types a and b exhibit dissimilar photophysical and biological properties. In vitro cytotoxicity tests conclusively prove that derivatives of series a are harmless in the dark against SW480 cancer cells (colon adenocarcinoma), but express enhanced cytotoxicity versus the same cells after stimulation with UV or blue light. In contrast, complexes of type b show a very high cytotoxic activity in the dark, but low photosensitizing ability. Thus, the ancillary N^O ligand is the main factor in terms of cytotoxic activity both in the dark and upon irradiation. However, the C^N ligands play a key role regarding cellular uptake. In particular, the complex of formula [Ir(dfppy)2(L1)] (dfppy=2‐(4,6‐difluorophenyl)pyridinate) [3 a] has been identified as both an efficient photosensitizer for 1O2 generation and a potential agent for photodynamic therapy. These capabilities are probably related to a combination of its notable cellular internalization, remarkable photostability, high photoluminescence quantum yield, and long triplet excited‐state lifetime. Both types of complexes exhibit notable catalytic activity in the photooxidation of thioanisole and S‐containing aminoacids with full selectivity.
2018-11
info:eu-repo/semantics/article
0947-6539
http://hdl.handle.net/10259/5041
10.1002/chem.201803784
eng
Chemistry-a european journal. 2018, V. 24, n. 66, p. 17523-17537
https://doi.org/10.1002/chem.201803784
info:eu-repo/grantAgreement/MINECO/CTQ2014-58812-C2-1-R
info:eu-repo/grantAgreement/MINECO/CTQ2014-58812-C2-2-R
info:eu-repo/grantAgreement/MINECO/CTQ2015-70371-REDT
info:eu-repo/grantAgreement/MINECO/CTQ2015-71353-R
info:eu-repo/grantAgreement/MINECO/CTQ2015-71154-P
info:eu-repo/grantAgreement/MINECO/MDM-2015-0538
info:eu-repo/grantAgreement/JCyL/BU299A12-1
info:eu-repo/grantAgreement/JCyL/BU042U16
info:eu-repo/grantAgreement/JCyL/BU051U16
info:eu-repo/grantAgreement/GVA/Prometeo2016-135
info:eu-repo/grantAgreement/FundaciónLaCaixa/LCF-PR-PR12-11070003
info:eu-repo/semantics/openAccess
Wiley-VCH Verlag