Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand

Transition metal complexes of Co(II), Cu(II), and Fe(II) bearing a rigid symmetrical 2,20 -(1,2-phenylene)bis (1H-benzimidazole) ligand, PhBIm2, were synthesized and fully characterized by ESI-MS, FT-IR, 1 H NMR (for paramagnetic species), UV–Vis spectroscopy and microanalytical techniques. Besides...

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Autores:: Chirinos, Juan
Ibarra, Darmenia
Morillo, Ángel
Llovera, Ligia
González, Teresa
Zárraga, Jeannette
Larreal, Oswaldo
Guerra, Mayamarú

Tipo de recurso:

Fecha de publicación:: 2021

Institución:: Universidad Tecnológica de Bolívar

Repositorio:: Repositorio Institucional UTB

Idioma:: eng

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network_name_str	Repositorio Institucional UTB
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dc.title.spa.fl_str_mv	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
title	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
spellingShingle	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand Catechol Quinone 2,2′-(1,2-phenylene)bis(1H-benzimidazole) Transition metal complexes LEMB
title_short	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
title_full	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
title_fullStr	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
title_full_unstemmed	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
title_sort	Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand
dc.creator.fl_str_mv	Chirinos, Juan Ibarra, Darmenia Morillo, Ángel Llovera, Ligia González, Teresa Zárraga, Jeannette Larreal, Oswaldo Guerra, Mayamarú
dc.contributor.author.none.fl_str_mv	Chirinos, Juan Ibarra, Darmenia Morillo, Ángel Llovera, Ligia González, Teresa Zárraga, Jeannette Larreal, Oswaldo Guerra, Mayamarú
dc.subject.keywords.spa.fl_str_mv	Catechol Quinone 2,2′-(1,2-phenylene)bis(1H-benzimidazole) Transition metal complexes
topic	Catechol Quinone 2,2′-(1,2-phenylene)bis(1H-benzimidazole) Transition metal complexes LEMB
dc.subject.armarc.none.fl_str_mv	LEMB
description	Transition metal complexes of Co(II), Cu(II), and Fe(II) bearing a rigid symmetrical 2,20 -(1,2-phenylene)bis (1H-benzimidazole) ligand, PhBIm2, were synthesized and fully characterized by ESI-MS, FT-IR, 1 H NMR (for paramagnetic species), UV–Vis spectroscopy and microanalytical techniques. Besides the cobalt complex was subject of X-ray structural analysis. The molecular crystal structure of the PhBIm2Co(II)Cl2 complex revealed the metal center in a pseudo-tetrahedral environment with not significant lengthening or compressing of the bonds in the PhBIm2 framework upon chelation of the ligand. All complexes catalyze the aerobic oxidation of o-catechol to o-quinone under mild conditions. The results show that the oxidation rate depends on the electronic stabilizing effect to the metal center rather than the steric hindrance of the ligand. Kinetic parameters (Vmax, kcat, KM) were estimated by mean of the Michaelis–Menten model and Lineweaver–Burk plot. Catechol oxidation rates of complexes 2–4 are in the same order of magnitudes of mononuclear and dinuclear Cu(II) complexes bearing imidazole-based ligands but lower than observed for the catecholase enzyme
publishDate	2021
dc.date.accessioned.none.fl_str_mv	2021-08-06T12:29:17Z
dc.date.available.none.fl_str_mv	2021-08-06T12:29:17Z
dc.date.issued.none.fl_str_mv	2021-04-24
dc.date.submitted.none.fl_str_mv	2021-08-05
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dc.identifier.citation.spa.fl_str_mv	Juan Chirinos, Darmenia Ibarra, Ángel Morillo, Ligia Llovera, Teresa González, Jeannette Zárraga, Oswaldo Larreal, Mayamarú Guerra, Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bis-benzimidazole ligand, Polyhedron, Volume 203, 2021, 115232, ISSN 0277-5387, https://doi.org/10.1016/j.poly.2021.115232.
dc.identifier.uri.none.fl_str_mv	https://hdl.handle.net/20.500.12585/10355
dc.identifier.doi.none.fl_str_mv	https://doi.org/10.1016/j.poly.2021.115232
dc.identifier.instname.spa.fl_str_mv	Universidad Tecnológica de Bolívar
dc.identifier.reponame.spa.fl_str_mv	Repositorio Universidad Tecnológica de Bolívar
identifier_str_mv	Juan Chirinos, Darmenia Ibarra, Ángel Morillo, Ligia Llovera, Teresa González, Jeannette Zárraga, Oswaldo Larreal, Mayamarú Guerra, Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bis-benzimidazole ligand, Polyhedron, Volume 203, 2021, 115232, ISSN 0277-5387, https://doi.org/10.1016/j.poly.2021.115232. Universidad Tecnológica de Bolívar Repositorio Universidad Tecnológica de Bolívar
url	https://hdl.handle.net/20.500.12585/10355 https://doi.org/10.1016/j.poly.2021.115232
dc.language.iso.spa.fl_str_mv	eng
language	eng
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dc.format.mimetype.spa.fl_str_mv	application/pdf
dc.format.size.none.fl_str_mv	7 páginas
dc.coverage.spatial.none.fl_str_mv	Colombia
dc.publisher.place.spa.fl_str_mv	Cartagena de Indias
dc.source.spa.fl_str_mv	Polyhedron, Volume 203, 2021.
institution	Universidad Tecnológica de Bolívar
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spelling	Chirinos, Juan01b06af8-ee35-43ab-bf60-561c77754563Ibarra, Darmeniad46e2807-e9b6-462f-bda4-09b38eea3e07Morillo, Ángel146c10d7-40ed-4592-85bb-92715c8dd361Llovera, Ligia8ebde7b3-0bcd-4cab-8644-fba0f1e771a8González, Teresae72c2089-9e9b-4061-9a43-b2f0798be6f6Zárraga, Jeannette7b88e84a-c331-45bd-8abc-bf361420ccc9Larreal, Oswaldocbf27a84-4d7f-447c-81e0-5fe7a43be796Guerra, Mayamarú5af72308-bd11-495a-86d4-0817f8961b6cColombia2021-08-06T12:29:17Z2021-08-06T12:29:17Z2021-04-242021-08-05Juan Chirinos, Darmenia Ibarra, Ángel Morillo, Ligia Llovera, Teresa González, Jeannette Zárraga, Oswaldo Larreal, Mayamarú Guerra, Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bis-benzimidazole ligand, Polyhedron, Volume 203, 2021, 115232, ISSN 0277-5387, https://doi.org/10.1016/j.poly.2021.115232.https://hdl.handle.net/20.500.12585/10355https://doi.org/10.1016/j.poly.2021.115232Universidad Tecnológica de BolívarRepositorio Universidad Tecnológica de BolívarTransition metal complexes of Co(II), Cu(II), and Fe(II) bearing a rigid symmetrical 2,20 -(1,2-phenylene)bis (1H-benzimidazole) ligand, PhBIm2, were synthesized and fully characterized by ESI-MS, FT-IR, 1 H NMR (for paramagnetic species), UV–Vis spectroscopy and microanalytical techniques. Besides the cobalt complex was subject of X-ray structural analysis. The molecular crystal structure of the PhBIm2Co(II)Cl2 complex revealed the metal center in a pseudo-tetrahedral environment with not significant lengthening or compressing of the bonds in the PhBIm2 framework upon chelation of the ligand. All complexes catalyze the aerobic oxidation of o-catechol to o-quinone under mild conditions. The results show that the oxidation rate depends on the electronic stabilizing effect to the metal center rather than the steric hindrance of the ligand. Kinetic parameters (Vmax, kcat, KM) were estimated by mean of the Michaelis–Menten model and Lineweaver–Burk plot. Catechol oxidation rates of complexes 2–4 are in the same order of magnitudes of mononuclear and dinuclear Cu(II) complexes bearing imidazole-based ligands but lower than observed for the catecholase enzymeapplication/pdf7 páginasenghttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://purl.org/coar/access_right/c_abf2Polyhedron, Volume 203, 2021.Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligandinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/restrictedAccesshttp://purl.org/coar/resource_type/c_2df8fbb1CatecholQuinone2,2′-(1,2-phenylene)bis(1H-benzimidazole)Transition metal complexesLEMBCartagena de IndiasInvestigadoresB. Kaim, Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life, John Wiley, 1994.T. Klabunde, C. Eicken, J.C. Sacchettini, B. Krebs, Crystal structure of a plant catechol oxidase containing a dicopper center, Nat. Struct. Biol. 5 (1998) 1084– 1090.M. Boice, F. Borcheta, A. Cunningham, J. Trent, Cosmestic compositions containing quinones and their topical use on skin and hair, US20180116928A1. (2018).T. Deming, Y. Miaoer, Synthesis and crosslinking of catechol containing copolypeptides, USOO6506577B1. (2003).G. Maier, C. Bernt, A. Butler, Catechol oxidation: Considerations in the design of wet adhesive materials, Biomater. Sci. 6 (2018) 332–339, https://doi.org/ 10.1039/c7bm00884h.J. Yang, M. Stuart, M. Kamperman, Jack of all trades: Versatile catechol crosslinking mechanisms, Chem. Soc. Rev. 43 (2014) 8271–8298, https://doi. org/10.1039/c4cs00185k.J. Bolton, T. Dunlap, Formation and biological targets of quinones: Cytotoxic versus cytoprotective effects, Chem. Res. Toxicol. 30 (2017) 13–37, https://doi. org/10.1021/acs.chemrestox.6b00256.B. Kim, D. Oh, S. Kim, J. Seo, D. Hwang, A. Masic, D. Han, H. Cha, Musselmimetic protein-based adhesive hydrogel, Biomacromol. 15 (2014) 1579– 1585, https://doi.org/10.1021/bm4017308.R. Marion, N. Saleh, N. Le Poul, D. Floner, O. Lavastre, F. Geneste, Rate enhancement of the catechol oxidase activity of a series of biomimetic monocopper(ii) complexes by introduction of non-coordinating groups in Ntripodal ligands, New J. Chem. 36 (2012) 1828–1835, https://doi.org/10.1039/ c2nj40265c.P. Wang, G. Yap, C. Riordan, Five-coordinate MII-semiquinonate (M = Fe, Mn, Co) complexes: Reactivity models of the catechol dioxygenases, Chem. Commun. 50 (2014) 5871–5873, https://doi.org/10.1039/c3cc49143aE. Mentasti, E. Pelizzetti, Reactions between iron(III) and catechol (odihydroxybenzene). Part I. Equilibria and kinetics of complex formation in aqueous acid solution, J. Chem. Soc. Dalt. Trans. (1973) 2605–2608, https://doi. org/10.1039/DT9730002605.P. Kamau, R. Jordan, Kinetic study of the oxidation of catechol by aqueous copper(II), Inorg. 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Scarpellini, Binuclear CuII Table 3 Kinetic parameters for aerobic oxidation of o-catechol to o-quinone with complexes 2–4. kcat 103 (s1 ) St Error KM (mM) St Error Vmax 103 (mM s1 ) St Error kcat/KM (M1 s 1 ) Ref. 2 6.10 0.73 118 21.3 6.10 21.3 0.0517 This work 3 1.57 0.13 110 9.9 1.57 9.9 0.014 This work 4 1.41 0.61 623 38.4 1.41 32.4 0.0023 This work a [CoL2]Cl 32.78 – 1.8 7.50x10-4 3.28 5.62x10-7 18.21 [55] b [Co3(OMe)4L2]ClO4 922 – 7.81 5.27x10-3 1.5 4.47x10-5 118.05 [56] c [Cu2(L)2(H2O)2] 866.67 – 4.3 – 104.6 – 201.55 [22] d CuLCl2 3.1 – 1.62 – – – 1.9 [9] e CuLCl2 60.1 – 0.28 – 1.30 – 214.64 [57] f CuLCl2 108.9 – 0.45 – 2.36 – 242 [57] h (L)FeIII(l-Ophenoxo)FeIII] 1.21 – 7.20 – – – 0.17 [58] a HL = (E)-2-((3-(2-hydroxyethylthio)propylimino)methyl)phenol; b H2L = N,N0 -dimethyl-N,N0 -bis(2-hydroxy-3,5-dimethylbenzyl)ethylenediamine; c H2L = 2-[(2-hydroxy-5-R-benzyl)amino]cyclohexane-1-carboxylic acid; d L = 6-(((1H-Pyrazol-1-yl)methyl)(thiophen-2-ylmethyl)amino)hexan-1-ol; e L = [(2-(pyridyl-2-yl)ethyl)((1-methylimidazol-2-yl)methyl)]imine; f L = [(2-(pyridyl-2-yl)ethyl)((1-methylimidazol-2-yl)methyl)]amine; h L = [(bbpmp)(H2O)(Cl)FeIII(l-Ophenoxo)FeIII(H2O)(Cl)]Cl J. 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Synthesis, characterization and catecholase biomimetic activity of novel cobalt(II), copper(II), and iron(II) complexes bearing phenylene-bisbenzimidazole ligand

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