Hydrolysis mechanism of anticancer drug lobaplatin in aqueous medium under neutral and acidic conditions: A DFT study

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

doi:10.1016/j.cplett.2016.10.004

Cited by 16 publications

(7 citation statements)

References 46 publications

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“…Activation energies (in KJ mol -1 ) for the hydrolysis of the studied complexes 1 and 2 are comparable to that of the clinically used anticancer drugs cisplatin [37,38], carboplatin [39], oxaliplatin [40], nedaplatin [41], lobaplatin [42] and picoplatin [11] in neutral conditions. The corresponding activation energy of step 1 (shown in red) and step 2 (shown in green) for hydrolysis of all these compounds are represented in Fig.…”

Section: Comparison Of Activation Energies With Currently Used Anticamentioning

confidence: 62%

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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Section: Comparison Of Activation Energies With Currently Used Anticamentioning

confidence: 62%

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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“…Therefore, the second hydrolysis of R and R ′ is kinetically as well as thermodynamically more favorable. The activation Gibbs free energies evaluated by DFT for the first and second hydrolysis of R and R ′ are found to be relatively lower in comparison to cisplatin (22.9 and 26.2 kcal/mol for first and second hydrolysis, respectively) and other platinum-based anticancer drugs. , …”

Section: Resultsmentioning

confidence: 88%

“…The activation Gibbs free energies evaluated by DFT for the first and second hydrolysis of R and R′ are found to be relatively lower in comparison to cisplatin (22.9 and 26.2 kcal/mol for first and second hydrolysis, respectively) and other platinum-based anticancer drugs. 51,52 2.2.2. Interactions of Aquated R Complexes with Cys and Sec.…”

Section: Resultsmentioning

confidence: 99%

Quantum Chemical Investigations on the Hydrolysis of Gold(III)-Based Anticancer Drugs and Their Interaction with Amino Acid Residues

2021

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A comprehensive hydrolysis mechanism of the promising class of Au(III) anticancer drugs [Au(DMDT)Cl 2 ] (DMDT = N,N-dimethyldithiocarbamate) (R) and [Au(damp)Cl 2 ] (damp = 2-[(dimethylamino)methyl]phenyl) (R′) was done by means of density functional theory (DFT) in combination with the CPCM solvation model to explore the solution behavior and stability under physiological conditions. The activation free energies (ΔG) for the second hydrolysis, R (13.7 kcal/mol) and R′ (10.0 kcal/mol) are found to be relatively lower in comparison to the first hydrolysis, and their rate constant values are computed to be 5.62 × 10 2 and 2.90 × 10 5 s −1 , respectively. Besides these, the interaction mechanisms of aquated R and R′ with the potential protein-binding sites cysteine (Cys) and selenocysteine (Sec) were also investigated in detail. The kinetic study and activation Gibbs free energy profiles reveal that the aquated complexes of R and R′ bind more effectively to the Se site of Sec than to the S site of Cys. Intra-and intermolecular hydrogen bonding play a pivotal role in stabilizing the intermediates and transition states involved in the ligand substitution reactions of R and R′. Natural population analysis (NPA) was done to determine the charge distributions on important atoms during the hydrolysis and ligand substitution reactions.

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“…The ligand detachment is described as the rate limiting step in acidic conditions and monohydrated complex reacts with DNA.The hydrolysis of Lobaplatin is presented on Fig. 13 (Reddy et al 2016).…”

Section: Medhanisms Of Hydrolysis Of Cisplatin Derivativesmentioning

confidence: 99%

Influence of chemical structure and mechanism of hydrolysis on pharmacological activity and toxicological profile of approved platinum drugs

Obreshkova¹,

Ivanova²,

Yordanova-Laleva³

2022

PHAR

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The problems with platinum complexes are resistance and toxicity of anticancer therapy. The aim of current study is the comparison of the influence of chemical structure and mechanism of hydrolysis on pharmacological activity and toxicological profile of approved in platinum drugs: Cisplatin, Carboplatin, Oxaliplatin, Nedaplatin, Lobaplatin, Heptaplatin, Satraplatin. Hydrolysis of Carboplatin and Nedaplatin occurs by double step hydration, to obtain the same active products as with Cisplatin: diaqudiamine-platinum. The similarity in mechanisms of hydrolysis of Oxaliplatin, Lobaplatin Heptaplatin, and Satraplatin is that the first part of the hydrolysis corresponds to the ring-opening and addition of the first water molecule, and in the second step of reaction occur the loss of the ligand and the formation of the di-aquated product by the addition of a second water molecule. Cisplatin, Carboplatin, and Oxaliplatin are nephrotoxic. Cisplatin and Heptaplatin are nephrotoxic. The similar dose-limiting effects of Carboplatin, Oxaliplatin, Nedaplatin, Lobaplatin, and Satraplatin is myelosuppression.

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Hydrolysis mechanism of anticancer drug lobaplatin in aqueous medium under neutral and acidic conditions: A DFT study

Cited by 16 publications

References 46 publications

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

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

Quantum Chemical Investigations on the Hydrolysis of Gold(III)-Based Anticancer Drugs and Their Interaction with Amino Acid Residues

Influence of chemical structure and mechanism of hydrolysis on pharmacological activity and toxicological profile of approved platinum drugs

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Hydrolysis mechanism of anticancer drug lobaplatin in aqueous medium under neutral and acidic conditions: A DFT study

Cited by 16 publications

References 46 publications

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

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

Quantum Chemical Investigations on the Hydrolysis of Gold(III)-Based Anticancer Drugs and Their Interaction with Amino Acid Residues

﻿Influence of chemical structure and mechanism of hydrolysis on pharmacological activity and toxicological profile of approved platinum drugs

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Influence of chemical structure and mechanism of hydrolysis on pharmacological activity and toxicological profile of approved platinum drugs