Synthesis and biological evaluation of copper (II) complexes of sterically hindered o-aminophenol derivatives as antimicrobial agents

Loginova, N. V.; Ковальчук, Т. В.; Желдакова, Римма Анатольевна; Osipovich, N. P.; Сорокин, В. Л.; Полозов, Г. И.; Ксендзова, Г. А.; Glushonok, G.K.; Chernyavskaya, A. A.; Шадыро, О. И.

doi:10.1016/j.bmcl.2006.07.065

Cited by 32 publications

(11 citation statements)

References 21 publications

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“…The outer membrane of Gram-negative bacteria is the first barrier capable of limiting the penetration of antimicrobial agents. This fact is widely known and referred to as ''intrinsic resistance" of Gram-negative bacteria [38]. Our study results had showed also the same effect.…”

Section: Antimicrobial Activitysupporting

confidence: 88%

Synthesis, spectroscopic, thermal, voltammetric studies and biological activity of crystalline complexes of pyridine-2,6-dicarboxylic acid and 8-hydroxyquinoline

Çolak

Yeşılel

et al. 2009

Journal of Molecular Structure

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Section: Antimicrobial Activitysupporting

confidence: 88%

Synthesis, spectroscopic, thermal, voltammetric studies and biological activity of crystalline complexes of pyridine-2,6-dicarboxylic acid and 8-hydroxyquinoline

Çolak

Yeşılel

et al. 2009

Journal of Molecular Structure

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“…Catalytic fate of copper ions towards molecular oxygen activation in selective and efficient oxidation reactions was paid substantial attention during last few decades for immense biological significance of copper ion in our living system . Copper, an essential bio‐metal, usually takes part as important oxygen carriers, and copper containing metalloenzymes in living system play fundamental role in revealing its catalytic role as dioxygen and/or substrates activators towards different bio‐functions . In this context, it shouldn't be out of place to mention that chemists have significantly contributed in unveiling the mystery of nature, specially by designing different metal complexes which can potentially mimic the active site of different metalloenzymes in nature .…”

Section: Introductionmentioning

confidence: 99%

Catalytic Fate of Two Copper Complexes towards Phenoxazinone Synthase and Catechol Dioxygenase Activity

Garai¹,

Dey²,

Yadav

et al. 2017

ChemistrySelect

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In this present work, we report the synthesis and structural characterization of two copper(II) complexes, [Cu(bpy)Cl2] (1) & [Cu(μ‐Cl)(phen)Cl]2 (2) [bpy=2,2′‐bipyridine; phen=1,10‐phenanthroline]. We have also studied their catalytic fate towards phenoxazinone synthase and catechol dioxygenase activity. X‐ray structural analyses revealed that 1 & 2 crystallize in triclinic & monoclinic system with P 1 and Cc space group respectively. The copper complexes catalyse the oxidative coupling of 2‐amino phenol (2‐AP) to aminophenoxazin‐3‐one with significant turn over number, kcat(h−1)=2.08×103 & 2.16×103 for 1 & 2 resectively. During investigation of catechol dioxygenase activity, stoichiometric addition of 1 & 2 to 3,5‐di‐tert‐butylcatechol (DTBC) in acetonitrile produce in situ catecholate‐to‐Cu(II) absorption bands at 812 and 821 nm respectively. The in situ Cu(II)‐catecholate species for both 1 & 2 react with molecular oxygen at the rate, kobs: 7.95×10−4 and 1.30×10−3 min−1 respectively and produce intradiol cleavage products in exclusive amount. Minor amount of benzoquinone is also found in solution. Intradiol products are found as major product in solution and accounts in favour of substrate activation mechanism.

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“…Although, the activation energies to produce compound 0, quantified in other work [40] ESR spectra of FePPic-I show a radical signal different to the reported for HRP-I [35][36][37][38][39][40]; although, it is possible that these signals contain the one at g ~ 2 for axial spectra of qms species and the axial spectra with s = 3/2. It is clear that each ESR spectrum is a snapshot of some of the changes in the oxidation state of the iron ion.…”

Section: Reaction Mechanismmentioning

confidence: 79%

Spectroscopic and Kinetic Characterization of Peroxidase-Like π-Cation Radical Pinch-Porphyrin-Iron(III) Reaction Intermediate Models of Peroxidase Enzymes

et al. 2016

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Abstract:The spectroscopic and kinetic characterization of two intermediates from the H 2 O 2 oxidation of three dimethyl ester [(proto), (meso), (deuteroporphyrinato) (picdien)]Fe(III) complexes ([FePPPic], [FeMPPic] and [FeDPPic], respectively) pinch-porphyrin peroxidase enzyme models, with s = 5/2 and 3/2 Fe(III) quantum mixed spin (qms) ground states is described herein. The kinetic study by UV/Vis at λ max = 465 nm showed two different types of kinetics during the oxidation process in the guaiacol test for peroxidases (1-3 + guaiacol + H 2 O 2 Ñ oxidation guaiacol products). The first intermediate was observed during the first 24 s of the reaction. When the reaction conditions were changed to higher concentration of pinch-porphyrins and hydrogen peroxide only one type of kinetics was observed. Next, the reaction was performed only between pinch-porphyrins-Fe(III) and H 2 O 2 , resulting in only two types of kinetics that were developed during the first 0-4 s. After this time a self-oxidation process was observed. Our hypotheses state that the formation of the π-cation radicals, reaction intermediates of the pinch-porphyrin-Fe(III) family with the ligand picdien [N,N'-bis-pyridin-2-ylmethyl-propane-1,3-diamine], occurred with unique kinetics that are different from the overall process and was involved in the oxidation pathway. UV-Vis, 1 H-NMR and ESR spectra confirmed the formation of such intermediates. The results in this paper highlight the link between different spectroscopic techniques that positively depict the kinetic traits of artificial compounds with enzyme-like activity.

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Synthesis and biological evaluation of copper (II) complexes of sterically hindered o-aminophenol derivatives as antimicrobial agents

Cited by 32 publications

References 21 publications

Synthesis, spectroscopic, thermal, voltammetric studies and biological activity of crystalline complexes of pyridine-2,6-dicarboxylic acid and 8-hydroxyquinoline

Synthesis, spectroscopic, thermal, voltammetric studies and biological activity of crystalline complexes of pyridine-2,6-dicarboxylic acid and 8-hydroxyquinoline

Catalytic Fate of Two Copper Complexes towards Phenoxazinone Synthase and Catechol Dioxygenase Activity

Spectroscopic and Kinetic Characterization of Peroxidase-Like π-Cation Radical Pinch-Porphyrin-Iron(III) Reaction Intermediate Models of Peroxidase Enzymes

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