Cyclopalladated complexes containing metformin and benzylamine derivatives: Synthesis, characterization, binding interactions with DNA and BSA, in vitro cytotoxicity studies

Karami, Kazem; Parsianrad, Fereshteh; Alinaghi, Moloud; Amirghofran, Zahra

doi:10.1016/j.ica.2017.07.020

Cited by 18 publications

(10 citation statements)

References 54 publications

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“…This band appears in the free metformin at 237 nm, assigned to the intra ligand transition. Slightly shift to lower energy in both complexes is consistent with the coordination of the metformin to the nickel metal . Low intense bands observed at 447 nm (ɛ max = 30.3 M ‐1 ) and 410 nm (ɛ max = 100 M ‐1 ) assigned to ligand to metal charge transfer transition for 1 and 2 , respectively.…”

Section: Resultsmentioning

confidence: 69%

“…Further, the results are in agreement to that reported by Karami et al . for related compounds . Binding constants are a measure of the stability of compound–BSA complex whereas the free energy ΔG ° shows the spontaneity/non‐spontaneity of compound–BSA binding .…”

Section: Resultsmentioning

confidence: 99%

“…Slightly shift to lower energy in both complexes is consistent with the coordination of the metformin to the nickel metal. [32] Low intense bands observed at 447 nm (ɛ max = 30.3 M -1 ) and 410 nm (ɛ max = 100 M -1 ) assigned to ligand to metal charge transfer transition for 1 and 2, respectively. The d-d transitions appear at 620 and 640 nm for complexes 1 and 2, respectively.…”

Section: S C H E M E 1 Syntheses Ni (Ii) Complexesmentioning

confidence: 98%

“…Further, the results are in agreement to that reported by Karami et al for related compounds. [32] Binding constants are a measure of the stability of compound-BSA complex whereas the free energy ΔG shows the spontaneity/non-spontaneity of compound-BSA binding. [36] The ΔG values, calculated using equation (4), are −6.92, −6.89, −7.24 and − 7.20 kcal M −1 for Met, IDA, 1 and 2, respectively and the negative sign for ΔG indicates the spontaneity of the binding of all compounds with proteins.…”

Section: Electronic Absorption Studiesmentioning

confidence: 99%

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Metformin Containing Nickel (II) Complexes: Synthesis, Structural Characterization, Binding and Kinetic Interactions with BSA, Antibacterial and in‐vitro Cytotoxicity Studies

El-Shami

Ramadan

Ibrahim

et al. 2020

Applied Organom Chemis

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In quest of antimicrobial and anticancer agents, metformin containing Ni (II) complexes, [Ni (Met)2]Cl·OH (1) and [Ni (Met)(IDA)] (2) {Met: metformin, IDA: iminodiacetic acid} were synthesized and X‐ray structure of 1 is four‐coordinate square planar geometry. Bovine serum albumin (BSA) interaction and binding studies to Met, IDA and their Ni (II) complexes were investigated and showed a strong interaction. A static quenching process was proposed at low concentrations of compounds whereas, combined quenching process was observed for 1 and 2 at higher concentrations. Kinetic stability, affinity and association constants of compounds‐BSA were studied using stopped‐flow technique and a mechanism was proposed: a fast and reversible step of BSA binding including complex formation and dissociation was proposed; for the second step, a reversible reaction was observed for 1 and 2 whereas, an irreversible reaction with Met and IDA was observed indicating that coordination with nickel ions change the interaction mechanism. Additionally, the antibacterial investigation against both Gram‐positive and Gram‐negative bacteria showed that all compounds exhibited significant activities. They also show cytotoxicity against HepG2 human liver cancer cell but the half maximal inhibitory concentration (IC50) values obtained for the cell lines were higher in comparison with cisplatin. Although Met‐BSA and IDA‐BSA are kinetically more stable than that of 1‐BSA and 2‐BSA, 1‐BSA and 2‐BSA showed better antibacterial and cytotoxic activities which is in agreement with the binding constants.

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Section: Resultsmentioning

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: S C H E M E 1 Syntheses Ni (Ii) Complexesmentioning

confidence: 98%

Section: Electronic Absorption Studiesmentioning

confidence: 99%

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Metformin Containing Nickel (II) Complexes: Synthesis, Structural Characterization, Binding and Kinetic Interactions with BSA, Antibacterial and in‐vitro Cytotoxicity Studies

El-Shami

Ramadan

Ibrahim

et al. 2020

Applied Organom Chemis

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“…Complex 85 was equally active against E. faecalis and Shigella as Zr complex 9, but did not display any activity against K. pneumoniae and S. aureus [105]. Pd(II)-metformin complexes 81-85 (Figure 3) were prepared using PdCl 2 or Pd(OAc) 2 as starting materials under the same experimental conditions as analogous Ni(II) complexes and their antimicrobial activity was compared [71,105,145,146]. Pd(II) complex 81 demonstrated similar antibacterial activity as Ni(II) complex 68.…”

Section: Group X (Ni Pd Pt)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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Supramolecular interaction of transition metal complexes with albumins and DNA: Spectroscopic methods of estimation of binding parameters

Galkina

Проскурнин

2018

Applied Organom Chemis

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Binding parameters of metal complexes with albumins and DNA since the middle of 1990s are considered and summarized. The most widespread spectroscopic methods of estimation of binding parameters are discusseddirect fluorescent methods, indirect fluorescent methods (by fluorescence quenching parameters), and ways of estimation of binding constants by other optical spectroscopic methods. The methods and approaches to calculations used for the determination of binding constants are discussed. The data on the already found binding constants and kinetic parameters is systematized.KEYWORDS albumins, DNA, metal complexes, proteins, supramolecular interaction Funding information: Russian Foundation for Basic Research, Grant/Award Number: 16-03-01089_a 16-53-50027_YaF_a Abbreviations and designations used: F 0 , fluorescence intensity in the absence of a quencher; F, fluorescence intensity in the presence of a acid); NTSC, a new thiosemicarbazone; o-cbiaH, 5-(2-carboxybenzyloxy)isophthalic acid; o-van-gln, a Schiff base derived from o-vanillin and glutamine; o-van-L-met, Schiff base derived from o-vanillin and L-methionine; oxo, 5-

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Cyclopalladated complexes containing metformin and benzylamine derivatives: Synthesis, characterization, binding interactions with DNA and BSA, in vitro cytotoxicity studies

Cited by 18 publications

References 54 publications

Metformin Containing Nickel (II) Complexes: Synthesis, Structural Characterization, Binding and Kinetic Interactions with BSA, Antibacterial and in‐vitro Cytotoxicity Studies

Metformin Containing Nickel (II) Complexes: Synthesis, Structural Characterization, Binding and Kinetic Interactions with BSA, Antibacterial and in‐vitro Cytotoxicity Studies

Biological Properties of Transition Metal Complexes with Metformin and Its Analogues

Supramolecular interaction of transition metal complexes with albumins and DNA: Spectroscopic methods of estimation of binding parameters

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