Inorganic Chemistry, volume 53, issue 20, pages 11274-11288
Derivation of Structure–Activity Relationships from the Anticancer Properties of Ruthenium(II) Arene Complexes with 2-Aryldiazole Ligands
Martínez Alonso Marta
1
,
Busto N
1
,
Jalón Félix A.
2
,
Manzano Blanca
2
,
Leal J M
1
,
Rodrı́guez A.
2
,
García Begoña
1
,
Espino Gustavo
1
1
Departamento de
Química, Facultad de Ciencias, Universidad de Burgos, Plaza Misael
Bañuelos s/n, 09001 Burgos, Spain
|
2
Departamento de
Química Inorgánica, Orgánica y Bioquímica,
Facultad de Químicas (IRICA), Universidad de Castilla—La Mancha, Avenida Camilo J. Cela 10, 13071 Ciudad Real, Spain
|
Publication type: Journal Article
Publication date: 2014-10-10
Journal:
Inorganic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.6
ISSN: 00201669, 1520510X
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The ligands 2-pyridin-2-yl-1H-benzimidazole (HL(1)), 1-methyl-2-pyridin-2-ylbenzimidazole (HL(2)), and 2-(1H-imidazol-2-yl)pyridine (HL(3)) and the proligand 2-phenyl-1H-benzimidazole (HL(4)) have been used to prepare five different types of new ruthenium(II) arene compounds: (i) monocationic complexes with the general formula [(η(6)-arene)RuCl(κ(2)-N,N-HL)]Y [HL = HL(1), HL(2), or HL(3); Y = Cl or BF4; arene = 2-phenoxyethanol (phoxet), benzene (bz), or p-cymene (p-cym)]; (ii) dicationic aqua complexes of the formula [(η(6)-arene)Ru(OH2)(κ(2)-N,N-HL(1))](Y)2 (Y = Cl or TfO; arene = phoxet, bz, or p-cym); (iii) the nucleobase derivative [(η(6)-arene)Ru(9-MeG)(κ(2)-N,N-HL(1))](PF6)2 (9-MeG = 9-methylguanine); (iv) neutral complexes consistent with the formulation [(η(6)-arene)RuCl(κ(2)-N,N-L(1))] (arene = bz or p-cym); (v) the neutral cyclometalated complex [(η(6)-p-cym)RuCl(κ(2)-N,C-L(4))]. The cytototoxic activity of the new ruthenium(II) arene compounds has been evaluated in several cell lines (MCR-5, MCF-7, A2780, and A2780cis) in order to establish structure-activity relationships. Three of the compounds with the general formula [(η(6)-arene)RuCl(κ(2)-N,N-HL(1))]Cl differing in the arene moiety have been studied in depth in terms of thermodynamic dissociation constants, aquation kinetic constants, and DNA binding measurements. The biologically most active compound is the p-cym derivative, which strongly destabilizes the DNA double helix, whereas those with bz and phoxet have only a small effect on the stability of the DNA double helix. Moreover, the inhibitory activity of several compounds toward CDK1 has also been evaluated. The DNA binding ability of some of the studied compounds and their CDK1 inhibitory effect suggest a multitarget mechanism for their biological activity.
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Martínez Alonso M. et al. Derivation of Structure–Activity Relationships from the Anticancer Properties of Ruthenium(II) Arene Complexes with 2-Aryldiazole Ligands // Inorganic Chemistry. 2014. Vol. 53. No. 20. pp. 11274-11288.
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Martínez Alonso M., Busto N., Jalón F. A., Manzano B., Leal J. M., Rodrı́guez A., García B., Espino G. Derivation of Structure–Activity Relationships from the Anticancer Properties of Ruthenium(II) Arene Complexes with 2-Aryldiazole Ligands // Inorganic Chemistry. 2014. Vol. 53. No. 20. pp. 11274-11288.
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TY - JOUR
DO - 10.1021/ic501865h
UR - https://doi.org/10.1021%2Fic501865h
TI - Derivation of Structure–Activity Relationships from the Anticancer Properties of Ruthenium(II) Arene Complexes with 2-Aryldiazole Ligands
T2 - Inorganic Chemistry
AU - Martínez Alonso, Marta
AU - Busto, N
AU - Jalón, Félix A.
AU - Manzano, Blanca
AU - Leal, J M
AU - Rodrı́guez, A.
AU - García, Begoña
AU - Espino, Gustavo
PY - 2014
DA - 2014/10/10 00:00:00
PB - American Chemical Society (ACS)
SP - 11274-11288
IS - 20
VL - 53
SN - 0020-1669
SN - 1520-510X
ER -
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@article{2014_Martínez Alonso,
author = {Marta Martínez Alonso and N Busto and Félix A. Jalón and Blanca Manzano and J M Leal and A. Rodrı́guez and Begoña García and Gustavo Espino},
title = {Derivation of Structure–Activity Relationships from the Anticancer Properties of Ruthenium(II) Arene Complexes with 2-Aryldiazole Ligands},
journal = {Inorganic Chemistry},
year = {2014},
volume = {53},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021%2Fic501865h},
number = {20},
pages = {11274--11288},
doi = {10.1021/ic501865h}
}
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MLA
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Martínez Alonso, Marta, et al. “Derivation of Structure–Activity Relationships from the Anticancer Properties of Ruthenium(II) Arene Complexes with 2-Aryldiazole Ligands.” Inorganic Chemistry, vol. 53, no. 20, Oct. 2014, pp. 11274-11288. https://doi.org/10.1021%2Fic501865h.