Biguanide–transition metals complexes as potential drug for hyperglycemia treatment

Villamizar-Delgado, Stephanny; Porras-Osorio, Laura M.; Piñeros, Octavio; Ellena, Javier; Balcazar, Norman; Varela-Miranda, Rubén Eduardo; D’Vries, Richard F.

doi:10.1039/d0ra04059b

Cited by 11 publications

(13 citation statements)

References 32 publications

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“…In another work, the cytotoxicity of 39 was tested against mouse muscle C2C12 cells and human liver carcinoma HepG2 cells [129]. Similar to 43, 39 did not show significant toxicity, indicating that it can be safely used as an antiviral agent or for other purposes [129]. Surprisingly, despite the lack of activity of complexes 41, 42 and 44 against influenza virus, they demonstrated excellent inhibitory potential of herpes simplex virus type 2 strain MS (HSV-2) [128].…”

Section: Group IX (Co Rh Ir)mentioning

confidence: 99%

Biological Properties of Transition Metal Complexes with Metformin and Its Analogues

2022

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Metformin is a widely prescribed medication for the treatment and management of type 2 diabetes. It belongs to a class of biguanides, which are characterized by a wide range of diverse biological properties, including anticancer, antimicrobial, antimalarial, cardioprotective and other activities. It is known that biguanides serve as excellent N-donor bidentate ligands and readily form complexes with virtually all transition metals. Recent evidence suggests that the mechanism of action of metformin and its analogues is linked to their metal-binding properties. These findings prompted us to summarize the existing data on the synthetic strategies and biological properties of various metal complexes with metformin and its analogues. We demonstrated that coordination of biologically active biguanides to various metal centers often resulted in an improved pharmacological profile, including reduced drug resistance as well as a wider spectrum of activity. In addition, coordination to the redox-active metal centers, such as Au(III), allowed for various activatable strategies, leading to the selective activation of the prodrugs and reduced off-target toxicity.

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Section: Group IX (Co Rh Ir)mentioning

confidence: 99%

Biological Properties of Transition Metal Complexes with Metformin and Its Analogues

2022

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“…Moreover, complexes [Ni(Hdmbg) 2 ]Cl(OH) and [Ni(Hdmbg)(ida)] (H 2 ida: iminodiacetic acid) have shown antiproliferative activity [16] whereas [Ni(Hdmbg)(dmbg)]Cl(OH)ÁH 2 O and [Cu(Hdmbg) 2 ]Cl 2 ÁH 2 O exhibited low cytotoxicity against human liver (HepG2) carcinoma cells. [17] This study provides supplementary spectral, electrochemical and geometry optimization data for mononuclear complexes of the type [ML]ÁnH 2 O (M: Ni, Cu, L: ligands resulted from the condensation of [M(dmbg) 2 ] with ammonia/hydrazine and formaldehyde) developed as biological active species. This approach was encouraged by the scarce information concerning biologically active complexes bearing macrocycle biguanide derivatives, for which the literature solely reports data concerning the ability of their Pd(II) complexes to inhibit S. aureus and Escherichia coli strains, both in planktonic and biofilm-embedded state.…”

Section: Introductionmentioning

confidence: 99%

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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“…[ 7–12 ] Instead, when it coordinates as a cation, the unidentate behaviour was observed and only with ions that prefer the tetrahedral coordination, such as Co(II) [ 6 ] and Zn(II). [ 13 ]…”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9][10][11][12] Instead, when it coordinates as a cation, the unidentate behaviour was observed and only with ions that prefer the tetrahedral coordination, such as Co(II) [6] and Zn(II). [13] The best known of these derivatives is metformin (N,N 0 -dimethylbiguanide, dmbg), prescribed for type II diabetes treatment, acting by decreasing the glucose release from the hepatic tissue. [14] Some recent studies indicated other biological activities, such as inhibiting cancer cell proliferation [15,16] or therapeutic potential for autoimmune diseases.…”

Section: Introductionmentioning

confidence: 99%

Copper(II) species with 1‐(o‐tolyl)biguanide: Structural characterization, ROS scavenging, antibacterial activity, biocompatibility and in silico studies

Maxim

Badea

Rostas

et al. 2021

Applied Organom Chemis

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The species cis‐[Cu(tbg)2](ClO4)2 (CuTP) (tbg: 1‐(o‐tolyl)biguanide) was designed as a novel antimicrobial and biocompatible agent. The single‐crystal X‐ray diffraction revealed a mononuclear species with a very interesting structure consisting of two tautomeric forms of tbg arranged in a cis‐configuration. A complex hydrogen bond network with perchlorate anions involved in different interactions leads to a supramolecular structure. The EPR data indicated the formation of a stable cis‐trans mixture in dimethylsulfoxide. Moreover, the EPR experiments evidenced no activity against the superoxide radical (O2·−) but scavenging ability of the hydroxyl radical (HO·). This complex exhibited excellent antibacterial properties against planktonic and biofilm embedded gram‐negative (Klebsiella pneumoniae, Enterobacter cloacae) and gram‐positive (Bacillus subtilis, Lysteria monocytogenes) bacteria. The best efficiency was noticed against E. cloacae and L. monocytogenes with minimal inhibitory concentration and minimal biofilm eradication for a concentration value of 1.95 μg/ml. One of the possible mechanisms of antimicrobial activity is represented by reactive oxygen species (ROS) generation. The complex was not cytotoxic on L929 fibroblasts. The in silico analysis confirmed the drug‐likeness and safety profile of the tested compound and its potential for developing novel antimicrobial and therapeutic tools, targeting other clinical conditions besides infectious diseases.

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Biguanide–transition metals complexes as potential drug for hyperglycemia treatment

Abstract: Coordination compounds of Cu(ii), Ni(ii), Co(ii), and Zn(ii) with a type of biguanide were obtained and structurally characterized. The new metal-drugs present biological applications as potential drugs for diabetes and metabolic syndrome.

Cited by 11 publications

References 32 publications

Biological Properties of Transition Metal Complexes with Metformin and Its Analogues

Biological Properties of Transition Metal Complexes with Metformin and Its Analogues

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

Copper(II) species with 1‐(o‐tolyl)biguanide: Structural characterization, ROS scavenging, antibacterial activity, biocompatibility and in silico studies

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