Thermal, spectral, electrochemical and biologic characterization of new Pd(II) complexes with ligands bearing biguanide moieties

Badea, Mihaela; Iosub, Elica; Chifiriuc, Mariana Carmen; Măruţescu, Luminiţa; Iorgulescu, Emilia Elena; Lazăr, Veronica; Marinescu, Dana; Bleoţu, Coralia; Olar, Rodica

doi:10.1007/s10973-012-2288-4

Cited by 9 publications

(9 citation statements)

References 35 publications

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“…A variety of complexes with anti-biofilm activity, ranging from species with known antibiotics or natural products to new synthetic ligands, mainly with low toxicity and chelating ability have been developed [ 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 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 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 , 113 , 114 , 115 , 116 , 117 ,…”

Section: Complexes With Antibiofilm Activitymentioning

confidence: 99%

“…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%

Section: Complexes With Antibiofilm Activitymentioning

confidence: 99%

Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

2022

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“…Some of the non-biological metal species might be relevant to medicinal or other applications of protease inhibition, e.g. platinum, vanadium, chromium, iridium, paladium, nickel, technetium, lanthanum, cesium, yttrium, samarium, and others (Woo et al 1999; Patrinoiu et al 2003; Fuks et al 2011; Al-Saif and Refat 2013; Badea et al 2013; Beygzadeh et al 2013; Shahabadi and Heidari 2014; Refat et al 2015; Mahmoud et al 2016; Chen et al 2018; Mihalache et al 2018). Metal toxicity is an obvious concern.…”

Section: The Stabilities Of Various Drug-metal-protease Complexes Arementioning

confidence: 99%

Biguanide is a modifiable pharmacophore for recruitment of endogenous Zn2+ to inhibit cysteinyl cathepsins: review and implications

Lockwood

2019

Biometals

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Excessive activities of cysteinyl cathepsins (CysCts) contribute to the progress of many diseases; however, therapeutic inhibition has been problematic. Zn 2 + is a natural inhibitor of proteases with CysHis dyads or CysHis(Xaa) triads. Biguanide forms bidentate metal complexes through the two imino nitrogens. Here, it is discussed that phenformin (phenylethyl biguanide) is a model for recruitment of endogenous Zn 2 + to inhibit CysHis/CysHis(X) peptidolysis. Phenformin is a Zn 2 + -interactive, anti-proteolytic agent in bioassay of living tissue. Benzoyl- l -arginine amide (BAA) is a classical substrate of papain-like proteases; the amide bond is scissile. In this review, the structures of BAA and the phenformin-Zn 2 + complex were compared in silico. Their chemistry and dimensions are discussed in light of the active sites of papain-like proteases. The phenyl moieties of both structures bind to the “S2” substrate-binding site that is typical of many proteases. When the phenyl moiety of BAA binds to S2, then the scissile amide bond is directed to the position of the thiolate-imidazolium ion pair, and is then hydrolyzed. However, when the phenyl moiety of phenformin binds to S2, then the coordinated Zn 2 + is directed to the identical position; and catalysis is inhibited. Phenformin stabilizes a “Zn 2 + sandwich” between the drug and protease active site. Hundreds of biguanide derivatives have been synthesized at the 1 and 5 nitrogen positions; many more are conceivable. Various substituent moieties can register with various arrays of substrate-binding sites so as to align coordinated Zn 2 + with catalytic partners of diverse proteases. Biguanide is identified here as a modifiable pharmacophore for synthesis of therapeutic CysCt inhibitors with a wide range of potencies and specificities. Graphical abstract Phenformin-Zn 2+ Complex

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“…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. [18] As a result, in order to develop a proper administration route for the most promising species, comparative antimicrobial and antitumour assays of the species bearing macrocycle ligands and their precursors were performed, alongside in silico analyses.…”

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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Thermal, spectral, electrochemical and biologic characterization of new Pd(II) complexes with ligands bearing biguanide moieties

Cited by 9 publications

References 35 publications

Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

Metal Complexes—A Promising Approach to Target Biofilm Associated Infections

Biguanide is a modifiable pharmacophore for recruitment of endogenous Zn2+ to inhibit cysteinyl cathepsins: review and implications

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

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