Cytotoxic, DNA binding and drug reservoir property of Pt(II)–sulfur complexes: In-vitro kinetics, mechanism with bio-relevant molecules in aqueous medium and a theoretical approach

Mukherjee, Subhajit; Mitra, Ishani; Reddy, P B Venkata; Mahata, Sujay; Bose, Chayanika; Dasgupta, Subrata; Linert, Wolfgang; Moi, Sankar Ch.

doi:10.1016/j.poly.2016.08.024

Cited by 13 publications

(7 citation statements)

References 53 publications

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“…On the other hand, hyperchromism can be attributed to external contact (surface binding) with the duplex . Furthermore, the observed hyperchromism and no shift in the location of the peak (258 nm) is indicative of partial or non‐intercalative‐binding modes (Figure ), such as dative bonds, electrostatic forces, hydrogen bonds, van der Waals forces and hydrophobic interactions . These hyperchromic shifts indicate that all the synthesized compounds interact with CT‐DNA with non‐intercalative‐binding modes.…”

Section: Resultsmentioning

confidence: 89%

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

Fekri

Salehi

Asadi

et al. 2017

Applied Organom Chemis

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Co(III) complexes of tridentate Schiff base ligands derived from N‐(2‐hydroxybenzylideneamino)benzamide (H2L1) and 2‐(2‐hydroxybenzylidene)hydrazine‐1‐carboxamide (H2L2) were synthesized and characterized using IR, Raman, 1H–NMR and UV–Vis spectroscopies. X‐ray single crystal structures of complexes 1 and 2 have also been determined, and it was indicated that these Co(III) complexes are in a distorted octahedral geometry. The cyclic voltammetry (CV) of the complexes indicates an irreversible redox behavior for both complexes 1 and 2. The antibacterial effects of the synthesized compounds have been tested by minimum inhibitory concentration and minimum bactericidal concentration methods, which suggested that the metal complexes exhibit better antibacterial effects than the ligands against Gram‐positive bacteria. The effects of the drug (drug = ligands and complexes) on bovine serum albumin (BSA) were examined using circular dichroism (CD) spectropolarimetry, and it was revealed that the BSA (BSA, as a carrier protein) secondary structure changed in the presence of the drug. Interaction of the drug with calf‐thymus DNA (CT‐DNA) was investigated by UV–Vis absorption, fluorescence emission, CV and CD spectroscopy. Binding constants were determined using UV–Vis absorption. The results indicated that the studied Schiff bases bind to DNA, with the hyperchromic effect and non‐intercalative mode in which the metal complexes are more effective than ligands. Furthermore, molecular docking simulation was used to obtain the energetic and binding sites for the interaction of the complexes with Mycobacterium tuberculosis enoyl‐acyl carrier protein reductase (InhA), and results showed that complex 1 has more binding energy.

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Section: Resultsmentioning

confidence: 89%

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

Fekri

Salehi

Asadi

et al. 2017

Applied Organom Chemis

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“…Electronic spectra of GSH- and dl -meth-substituted products C-3 and C-4 (Figure ) display hyperchromism along with the hypsochromic shift. The formation of new products can be explained by considering the spectral changes due to n → π* and n → σ* transition of their respective ligands in C-3 and C-4 . The spectrum of C-3 exhibits λ max at 210 nm with shouldering at 301.5 nm.…”

Section: Resultsmentioning

confidence: 93%

“…EtBr strongly intercalates to DNA adjacent bases through the displacement reaction as it structurally resembles the DNA base pair, resulting in an intense fluorescence emission peak at 600 nm. The entire procedure was performed by obeying the conditions which are previously reported. , The EtBr-DNA complex was prepared in Tris-HCl buffer with 20 μm both solutions to keep the [EtBr]/[CT-DNA] = 1:1 ratio. Before recording the emission spectrum of the EtBr/CT-DNA-bound complex, 30 min incubation period under dark condition was provided.…”

Section: Methodsmentioning

confidence: 99%

Development of Anticancer Activity of the Pt(II) Complex with N-Heterocyclic Amine: Its In Vitro Pharmacokinetics with Thiol and Thio-Ethers, DNA and BSA Binding, and Cell Cycle Arrest

Pan

Mitra

Mukherjee

et al. 2021

ACS Appl. Bio Mater.

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A dichloro Pt(II) complex with N-heterocyclic amine cis-Pt(PIEAM)Cl2, C-1 (where PIEAM = 1-(2-aminoethyl)piperidine) was synthesized and hydrolyzed to the corresponding [Pt(PIEAM)(OH2)2]2+ C-2 to explore its bioactivity and cytotoxic property. Biorelevant sulfur-containing small tripeptide glutathione (GSH)- and amino acid dl-methionine (dl-meth)-substituted complexes [Pt(PIEAM)(GSH)] C-3 and [Pt(PIEAM)(dl-meth)]+2 C-4 were synthesized and characterized. In vitro pharmacokinetic reactions of complex C-2 → C-3 and C-4 with GSH and dl-meth, respectively, were studied under pseudo-first-order reaction conditions. The high and negative entropy of activation (ΔS ⧧) and low and positive enthalpy of activation (ΔH ⧧) values were deduced from the Eyring equation to propose an associative mechanism. To find out the biotransformation of complex C-1, C-2, and Pt(II)–S chelates C-3 and C-4 to Pt(II)-DNA adducts, DNA binding affinity of C-1–C-4 was examined by UV–visible spectroscopy, fluorescence quenching, and gel electrophoresis methods. BSA binding activity of these complexes was emphasized for their biological importance and the “drug reservoir” activity. Anticancer activity of these complexes on HEp 2 (laryngeal), MDA-MB-231 (breast), and A549 (lung) cancer cell lines was found to be remarkable as compared to the recognized anticancer drugs such as cisplatin, carboplatin, and oxaliplatin. Cell cycle arrest was also explored on HEp 2 cells of the complexes at a concentration corresponding to IC50 value and displayed significant cell death at the sub-G1 phase.

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“…For rational drug designing and their clinical success, a mechanistic insight of cytotoxic metal complexes is important [18]. [19,20]. All these complexes had been reasonably designed taking the carrier ligand, 2-[(Methylamino)methyl]pyridine (MAMP), which is a σ-donor as well as π-acceptor and can tune the substitution of chloride ion by water.…”

Section: Introductionmentioning

confidence: 99%

“…All these complexes had been reasonably designed taking the carrier ligand, 2-[(Methylamino)methyl]pyridine (MAMP), which is a σ-donor as well as π-acceptor and can tune the substitution of chloride ion by water. Kinetic investigation of these complexes with various sulfur containing bio-molecules were performed [19][20][21] and the respective rate constants were evaluated. We had also reported the DNA binding property of the complex 1 and 3 experimentally as well as theoretically.…”

Section: Introductionmentioning

confidence: 99%

Hydrolysis mechanism of (N, N) chelated cytotoxic Pt/Pd(II)-dichloro complexes: A theoretical approach

Mukherjee

Reddy

Mitra

et al. 2017

Chemical Physics Letters

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Cytotoxic, DNA binding and drug reservoir property of Pt(II)–sulfur complexes: In-vitro kinetics, mechanism with bio-relevant molecules in aqueous medium and a theoretical approach

Cited by 13 publications

References 53 publications

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

Development of Anticancer Activity of the Pt(II) Complex with N-Heterocyclic Amine: Its In Vitro Pharmacokinetics with Thiol and Thio-Ethers, DNA and BSA Binding, and Cell Cycle Arrest

Hydrolysis mechanism of (N, N) chelated cytotoxic Pt/Pd(II)-dichloro complexes: A theoretical approach

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