Synthesis, characterization, and biological activity of some complex combinations of nickel with α-ketoglutaric acid and 1-(o-tolyl)biguanide

Mihalache, Mădălina; Oprea, Ovidiu; Guran, Cornelia; Holban, Alina Maria

doi:10.1016/j.crci.2017.11.011

Cited by 4 publications

(2 citation statements)

References 25 publications

(9 reference statements)

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“…The most recent data concerning these aspects are presented in this review, with highlights on examples of complexes with antibiotics [ 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 ], N-heterocycle derivatives [ 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 ], Schiff bases [ 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 ], biguanides [ 111 , 112 , 113 , 114 , 115 , 116 , 117 , 118 , 119 , …”

Section: Complexes With Antibiofilm Activitymentioning

confidence: 99%

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Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

2022

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Microbial biofilms are represented by sessile microbial communities with modified gene expression and phenotype, adhered to a surface and embedded in a matrix of self-produced extracellular polymeric substances (EPS). Microbial biofilms can develop on both prosthetic devices and tissues, generating chronic and persistent infections that cannot be eradicated with classical organic-based antimicrobials, because of their increased tolerance to antimicrobials and the host immune system. Several complexes based mostly on 3D ions have shown promising potential for fighting biofilm-associated infections, due to their large spectrum antimicrobial and anti-biofilm activity. The literature usually reports species containing Mn(II), Ni(II), Co(II), Cu(II) or Zn(II) and a large variety of multidentate ligands with chelating properties such as antibiotics, Schiff bases, biguanides, N-based macrocyclic and fused rings derivatives. This review presents the progress in the development of such species and their anti-biofilm activity, as well as the contribution of biomaterials science to incorporate these complexes in composite platforms for reducing the negative impact of medical biofilms.

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Section: Complexes With Antibiofilm Activitymentioning

confidence: 99%

“…As for complexes with mixed ligands, [M(Htbg)(Hkg)]X ( 47 ) (M: Ni, Cu; H 2 kg: α-ketoglutaric acid; X: Cl, CH 3 COO, NO 3 ) exhibited good activity against S. aureus and E. coli , both in the planktonic and biofilm growth states [ 120 , 121 ].…”

Section: Complexes With Antibiofilm Activitymentioning

confidence: 99%

Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

2022

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Synthesis, physico‐chemical characterization and bioevaluation of Ni(II), Pd(II), and Pt(II) complexes with 1‐(o‐tolyl)biguanide: Antimicrobial and antitumor studies

Nuţă

Badea

Chifiriuc

et al. 2020

Applied Organom Chemis

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New complexes of type [M(tbg)2]Cl2 [tbg = 1‐(o‐tolyl)biguanide; M = Ni(II), Pd(II), and Pt(II)] were synthesized and characterized to develop new biologically active compounds. The features of the complexes were assigned from microanalytical and thermal data. The NMR, FT‐IR, and UV‐Vis spectra were established by comparison with HtbgCl. All complexes exhibit a square‐planar geometry resulting from the chelating behavior of tbg. The HtbgCl and [Ni(tbg)2]Cl2 complexes were fully characterized by single‐crystal X‐ray diffraction. The HtbgCl species crystallize in the monoclinic C2/c spatial group, while the Ni(II) complex adopts an orthorhombic Pna21 spatial group. The structure is stabilized by a complex hydrogen bonds network. The in vitro antimicrobial assays revealed improved antimicrobial activity for complexes in comparison with the ligand against both planktonic and biofilm embedded microbial cells. The most efficient compound, showing the largest spectrum of antimicrobial activity, including Gram‐positive and Gram‐negative bacteria, as well as fungal strains, in both planktonic and biofilm growth states was the Pd(II) complex, followed by the Pt(II) complex. The Pt(II) compound exhibited the most significant antiproliferative activity on the human cervical cancer SiHa cell line, inducing a cell cycle arrest in the G2/M phase.

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Insight on Ni(II) and Cu(II) complexes of biguanide derivatives developed as effective antimicrobial and antitumour agents

Badea

Grecu

Chifiriuc

et al. 2021

Applied Organom Chemis

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ammonia and formaldehyde and H 2 L 2 : ligand resulted from the condensation of (4) with hydrazine and formaldehyde) were characterized as mononuclear species through information provided by NMR, electronic paramagnetic resonance (EPR) and UV-Vis spectroscopy as well as cyclic voltammetry. All data are consistent with macrocyclic formation by condensation. The complexes adopt a distorted square planar geometry resulting from the chelating behaviour of the corresponding ligands. The EPR spectra recorded after the addition of Cu(II) complexes into the corresponding Ni(II) complexes show a well resolved hyperfine structure with the superhyperfine pattern corresponding to four nitrogen atom donors. The cathodically shift of E pc2 for both series can be correlated with the increased stability of the M(I) species through macrocyclic ligands. Geometry optimization studies for complexes (2), (3), (5) and (6) have further confirmed the experimental data. The pharmacokinetic computational results indicate that the complexes exhibit medium to low intestinal absorption and slow blood-brain barrier permeability but low toxicity. Their predictive pharmacodynamic profiles show that the compounds present the ability to inhibit protease activity. By corroborating the results of the in silico analysis

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Synthesis, characterization, and biological activity of some complex combinations of nickel with α-ketoglutaric acid and 1-(o-tolyl)biguanide

Cited by 4 publications

References 25 publications

Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

Synthesis, physico‐chemical characterization and bioevaluation of Ni(II), Pd(II), and Pt(II) complexes with 1‐(o‐tolyl)biguanide: Antimicrobial and antitumor studies

Insight on Ni(II) and Cu(II) complexes of biguanide derivatives developed as effective antimicrobial and antitumour agents

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