Novel multifunctional and multitarget homo- ...
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Article dans une revue scientifique
DOI :
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Title :
Novel multifunctional and multitarget homo- (Fe2) and heterobimetallic [(Fe,M) with M = Re or Mn] sulfonyl hydrazones
Author(s) :
Huentupil, Yosselin [Auteur]
Chung, Patricio [Auteur]
Novoa, Néstor [Auteur]
Arancibia, Rodrigo [Auteur]
Roussel, Pascal [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Oyarzo, Juan [Auteur]
Instituto de Química
Klahn, A. Hugo [Auteur]
Instituto de Química
Silva, Carlos [Auteur]
Universidad de Chile = University of Chile [Santiago] [UCHILE]
Calvis, Carme [Auteur]
Messeguer, Ramon [Auteur]
Bosque, Ramón [Auteur]
Universitat de Barcelona [UB]
López, Concepción [Auteur]
Universitat de Barcelona [UB]
Chung, Patricio [Auteur]
Novoa, Néstor [Auteur]
Arancibia, Rodrigo [Auteur]
Roussel, Pascal [Auteur]

Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Oyarzo, Juan [Auteur]
Instituto de Química
Klahn, A. Hugo [Auteur]
Instituto de Química
Silva, Carlos [Auteur]
Universidad de Chile = University of Chile [Santiago] [UCHILE]
Calvis, Carme [Auteur]
Messeguer, Ramon [Auteur]
Bosque, Ramón [Auteur]
Universitat de Barcelona [UB]
López, Concepción [Auteur]
Universitat de Barcelona [UB]
Journal title :
Dalton Transactions
Abbreviated title :
Dalton Trans.
Volume number :
49
Pages :
12249-12265
Publisher :
Royal Society of Chemistry (RSC)
Publication date :
2020-07
HAL domain(s) :
Chimie
English abstract : [en]
The synthesis and characterization of the novel ferrocenyl sulfonyl hydrazide [Fe(η5-C5H5){(η5-C5H4)–S(O)2–NH–NH2}] (2) is reported. Additional studies on its reactivity using acetone or the ferrocenyl-, cyrhetrenyl- or ...
Show more >The synthesis and characterization of the novel ferrocenyl sulfonyl hydrazide [Fe(η5-C5H5){(η5-C5H4)–S(O)2–NH–NH2}] (2) is reported. Additional studies on its reactivity using acetone or the ferrocenyl-, cyrhetrenyl- or cymantrenyl-aldehydes have allowed us to isolate and characterize [Fe(η5-C5H5){(η5-C5H4)–S(O)2–NH–N[double bond, length as m-dash]CMe2}] (3), the bis(ferrocenyl) derivative [Fe(η5-C5H5){[(η5-C5H4)–S(O)2–NH–N[double bond, length as m-dash]CH–(η5-C5H4)]Fe(η5-C5H5)}] (4) and the heterodimetallic compounds [Fe(η5-C5H5){[(η5-C5H4)–S(O)2–NH–N[double bond, length as m-dash]CH–(η5-C5H4)]M(CO)3}] with M = Re (5a) or Mn (5b). The X-ray crystal structures of compounds 3, 5a and 5b are also reported. A comparative study of their electrochemical and spectroscopic properties is also described. Additional computational calculations based on the DFT methodology have allowed us to elucidate the effect produced by the replacement of the terminal –NH2 (in 2) by the –N[double bond, length as m-dash]CMe2 (in 3) and –N[double bond, length as m-dash]CHR (in 4, 5a and 5b) moieties on the electronic distribution and to explain the differences detected in their electrochemical properties and absorption spectra. In vitro cytotoxicity studies of compounds 2, 4, 5a and 5b on the HCT-116 (colon), MCF7 and MDA-MB231 (breast) cancer cell lines reveal that compound 2 has no significant activity (IC50 > 100 μM), while its derivatives 4, 5a and 5b proved to be active in the three cancer cell lines selected in this study. The growth inhibition potency of compounds 5a and 5b against the triple negative MDA-MB231 breast cancer cell line is similar (or slightly) greater than that of cisplatin. Moreover, compounds 2, 4, 5a and 5b are less toxic than cisplatin in the normal and non-tumoral BJ fibroblasts, and the heterodimetallic complexes 5a and 5b with selective index >2.1 show an outstanding selective toxicity towards the MDA-MB231 cancer cells.Show less >
Show more >The synthesis and characterization of the novel ferrocenyl sulfonyl hydrazide [Fe(η5-C5H5){(η5-C5H4)–S(O)2–NH–NH2}] (2) is reported. Additional studies on its reactivity using acetone or the ferrocenyl-, cyrhetrenyl- or cymantrenyl-aldehydes have allowed us to isolate and characterize [Fe(η5-C5H5){(η5-C5H4)–S(O)2–NH–N[double bond, length as m-dash]CMe2}] (3), the bis(ferrocenyl) derivative [Fe(η5-C5H5){[(η5-C5H4)–S(O)2–NH–N[double bond, length as m-dash]CH–(η5-C5H4)]Fe(η5-C5H5)}] (4) and the heterodimetallic compounds [Fe(η5-C5H5){[(η5-C5H4)–S(O)2–NH–N[double bond, length as m-dash]CH–(η5-C5H4)]M(CO)3}] with M = Re (5a) or Mn (5b). The X-ray crystal structures of compounds 3, 5a and 5b are also reported. A comparative study of their electrochemical and spectroscopic properties is also described. Additional computational calculations based on the DFT methodology have allowed us to elucidate the effect produced by the replacement of the terminal –NH2 (in 2) by the –N[double bond, length as m-dash]CMe2 (in 3) and –N[double bond, length as m-dash]CHR (in 4, 5a and 5b) moieties on the electronic distribution and to explain the differences detected in their electrochemical properties and absorption spectra. In vitro cytotoxicity studies of compounds 2, 4, 5a and 5b on the HCT-116 (colon), MCF7 and MDA-MB231 (breast) cancer cell lines reveal that compound 2 has no significant activity (IC50 > 100 μM), while its derivatives 4, 5a and 5b proved to be active in the three cancer cell lines selected in this study. The growth inhibition potency of compounds 5a and 5b against the triple negative MDA-MB231 breast cancer cell line is similar (or slightly) greater than that of cisplatin. Moreover, compounds 2, 4, 5a and 5b are less toxic than cisplatin in the normal and non-tumoral BJ fibroblasts, and the heterodimetallic complexes 5a and 5b with selective index >2.1 show an outstanding selective toxicity towards the MDA-MB231 cancer cells.Show less >
Language :
Anglais
Peer reviewed article :
Oui
Audience :
Non spécifiée
Administrative institution(s) :
Université de Lille
CNRS
Centrale Lille
ENSCL
Univ. Artois
CNRS
Centrale Lille
ENSCL
Univ. Artois
Collections :
Research team(s) :
Matériaux inorganiques, structures, systèmes et propriétés (MISSP)
Submission date :
2020-09-16T07:18:25Z
2020-09-25T10:59:23Z
2020-09-25T10:59:23Z
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