Copper(II) interaction with 3,5-diisopropylsalicylic acid (Dips): New insights on its role as a potential OH inactivating ligand

Brumas, Véronique; Miche, Hélène; Fiallo, Marina

doi:10.1016/j.jinorgbio.2006.11.017

Cited by 9 publications

(1 citation statement)

References 32 publications

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“…In this context, salicylic acid (SA) and its derivatives, as well as their metal complexes have gained much attention because of its associated pharmaceutical activities (Perrin, 1958;Hallmen et al, 1995, Wani et al 2017a). In few cases, it has been noticed that the drug activity increases, when SA is administered as metal chelates, for instance in the inhibition of the growth of tumor cells (Brumas, 1995;Brumas, 2007 andWani et al 2017b). Quoting an example, the mono and di-substituted chloro-derivatives of salicylic acid have been shown to be biologically active (Kantouch et al 2013 andShi et al 2007).…”

Section: Introductionmentioning

confidence: 99%

Complexation of trichlorosalicylic acid with alkaline and first row transition metals as a switch for their antibacterial activity

Kumar

Chawla

Cavallo

et al. 2018

Inorganica Chimica Acta

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CitationKumar V, Chawla M, Cavallo L, Basit Wani A, Manhas A, et al. (2017) Complexation of trichlorosalicylic acids by alkaline and first row transition metals as a switch for their antibacterial activity. Inorganica Chimica Acta. Available: http:// dx.NirajUpadhyay, Complexation of trichlorosalicylic acids by alkaline and first row transition metals as a switch for their antibacterial activity, Inorganica Chimica Acta (2017), doi: http://dx. Abstract:3,5,6-trichlorosalicylic acid (TCSA) does not show a good antibacterial activity. In contrast, here metal complexes with TCSA have shown better antibacterial activity for selected bacterial strains with a good degree of selectivity. Amongst the eight synthesized essential metal complexes complexed with TCSA, Mn(II)-TCSA and Ni(II)-TCSA have been found to be more effective with MIC range 20-50 µg/L as compared to control (chloramphenicol). The activity of an individual complex against different microbes was not found to be identical, indicating the usage of an individual metal chelate against a targeted bacterial strain. Further, the protein (BSA) binding constant of TCSA and its metal complexes were determined and ordered as Ca(II)-TCSA > Cu(II)-TCSA > Mg(II)-TCSA >> Mn(II)-TCSA >> Zn(II)-TCSA >>> Ni(II)-TCSA >>> Co(II)-TCSA > Fe(II)-TCSA > TCSA. The present study has confirmed enhanced antibacterial activities and binding constants for metal chelates of TCSA as compared to free TCSA, which seems directly related with the antioxidant activities of these complexes. Further, bearing the ambiguity related to the structural characterization of the metal complexed with TCSA ligands, DFT calculations have been used as the tool to unravel the right environment around the metals, studying basically the relative stability of square planar and octahedral metal complexes with TCSA.

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Section: Introductionmentioning

confidence: 99%

Complexation of trichlorosalicylic acid with alkaline and first row transition metals as a switch for their antibacterial activity

Kumar

Chawla

Cavallo

et al. 2018

Inorganica Chimica Acta

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Reactivity of substituted copper(II) salicylates with tert‐butylperoxyl radical: Structure–reactivity relationships

Tavadyan

Minasyan

Musaelyan

et al. 2009

Int J of Chemical Kinetics

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Absolute rate constants (k eff ) for the chemical reactions of Cu(II) 2 (3,5-di-iso-propylsalicylate) 4 (H 2 O) 3 , Cu(II) 2 (3,5-di-tert-butylsalicylate) 4 , Cu(II) 2 (3,5-di-tert-butylsalicylate) 4 (H 2 O) 4 , Cu(II) 2 (3,5-dimethylsalicylate) 4 (H 2 O) 3 , Cu(II) 2 (3-ethylsalicylate) 4 (H 2 O), Cu(II) 2 (3-phenylsalicylate) 4 , and Cu(II)(3,5-di-iso-propylsalicylate) 2 (pyridine) 2 with tertbutylperoxyl radical were determined using kinetic electron paramagnetic resonance measurements in 10% toluene in the hexane medium at temperatures ranging from −63 • C to 2 • C. These antioxidant (AO) chelates were ranked by their reactivity as follows:Cu(II)(3,5-di-isopropylsalicylate) 2 (pyridine) 2 at 20 • C. Differential pulse voltammetry was used to determine redox behavior of these chelates in CH 2 Cl 2 . Two types of salicylic OH groups were detected in these Cu(II) salicylates, characterized by the presence or absence of AO reactivity. One of them REACTIVITY OF SUBSTITUTED COPPER(II) SALICYLATES WITH TERT-BUTYLPEROXYL RADICAL 57was coordinate covalently bonded to Cu(II) via the oxygen atoms of the salicylic OH groups, displaying oxidation peak potentials in the range from +650 to 970 mV versus Ag/Ag + . The second type was intramolecularly hydrogen bonded to carboxylate oxygens, with an oxidation peak potential in the range from +1100 to 1200 mV versus Ag/Ag + . It was concluded that nonhydrogen-bonded salicylic OH groups are responsible for the antiperoxyl radical reactivity of these chelates, while neither Cu(II) nor salicylate ligands displayed reactivity with peroxyl radical. It has been established in this research that axially bonded electron pair donors such as pyridine and water decrease H-donating reactivity of Cu(II) salicylates by promoting the formation of intramolecular hydrogen bonding between the salicylic OH hydrogen atoms and carboxylate oxygen atoms in the salicylic ligands. Dependences of log k eff at 20 • C and the anodic oxidation potential (E pa ) for the salicylic OH group on the difference between symmetric and asymmetric stretching frequencies of carboxylate groups (in Fourier transform infrared spectra) for the substituted Cu(II) salicylates were determined. C 2009 Wiley Periodicals, Inc. Int J Chem Kinet 42: [56][57][58][59][60][61][62][63][64][65][66][67] 2010

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Synthesis and Anti-Inflammatory Activity of Tyrosol and Its Structural Analogs

et al. 2019

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Copper(II) interaction with 3,5-diisopropylsalicylic acid (Dips): New insights on its role as a potential OH inactivating ligand

Cited by 9 publications

References 32 publications

Complexation of trichlorosalicylic acid with alkaline and first row transition metals as a switch for their antibacterial activity

Complexation of trichlorosalicylic acid with alkaline and first row transition metals as a switch for their antibacterial activity

Reactivity of substituted copper(II) salicylates with tert‐butylperoxyl radical: Structure–reactivity relationships

Synthesis and Anti-Inflammatory Activity of Tyrosol and Its Structural Analogs

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