Carboplatin and oxaliplatin decomposition in chloride medium, monitored by XAS

Curis, Emmanuel; Provost, Karine; Bouvet, Diane; Nicolis, Ioannis; Crauste–Manciet, Sylvie; Brossard, Denis; Bénazeth, S.

doi:10.1107/s0909049500017775

Cited by 27 publications

(21 citation statements)

References 12 publications

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“…A recent contribution by Sarmah et al reports the optimized structure of oxaliplatin in vacuum and within the conductor-like screening model (COSMO) to take the solvent into account in the sense of a continuum using density functional theory (DFT). [18] In both phases they find bond lengths and bond angles close to the X-ray [17] and EXAFS [11,12] data and a chair configuration of the cyclohexane ring with the two amine groups in equatorial positions. In two classical molecular dynamics (CL-MD) simulations performed by Scheeff et al [19] and Sharma et al [20] the oxaliplatin-DNA adduct is characterized.…”

Section: Introductionmentioning

confidence: 70%

“…The only structural determination of oxaliplatin in aqueous solution comes from the contributions of Provost and collaborators who have characterized it by means of EXAFS spectroscopy. [11,12] In their measurements, they find four equivalent first-shell PtÀO and PtÀN distances of 2.00 , as well as a PtÀC distance of 2.82 (C atoms belonging to both ethyldiamine and oxalate ligands) and a Pt···O distance of 4.00 for the outer O atoms in oxalate. These values are in good agreement with previous crystallographic data (of 2.03, 2.83 and 4.00 , respectively).…”

Section: Introductionmentioning

confidence: 98%

“…Several studies have appeared on the substitution kinetics and chemical stability of oxaliplatin in water solution, [9,10] in NaCl solution, [9] and in the presence of different chemical species (such as chloride anions, [11,12] diethyl dithiocarbamate, [13] carbonate buffers, [14] different nucleophiles, [15,16] etc.). The only structural determination of oxaliplatin in aqueous solution comes from the contributions of Provost and collaborators who have characterized it by means of EXAFS spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

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Characterizing Pt‐Derived Anticancer Drugs from First Principles: The Case of Oxaliplatin in Aqueous Solution

Beret¹,

Pappalardo²,

Marx³

et al. 2009

ChemPhysChem

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The molecular compound ethyldiamine-oxalatoplatinum(II), EDO-Pt, is used as a model to study the oxaliplatin anticancer drug in aqueous solution by means of ab initio computer simulation. Gas-phase structure optimizations have been performed for both oxaliplatin and its EDO-Pt mimic along with Car-Parrinello molecular dynamics simulations of EDO-Pt in gas phase and in aqueous solution. The coordination of Pt(II) is square-planar on average, with Pt-N and Pt-O(I) distances of 2.04 A in solution. The diamine ligand has a bent structure, while the oxalate ligand is planar on average. The complex features a very rigid structure during the simulation and the charge distribution describes a dipole with its negative pole on the oxalate ligand and the positive pole on the Pt-diamine side. The solvation pattern of EDO-Pt is most well-defined around the amine and oxalate groups and is quantified by means of radial and spatial distribution functions of water molecules around the complex. Decomposition of radial distribution functions into their contributions from different regions (axial and equatorial) reveals an "anionic hydration" pattern of the metal cation by the solvent, which is analogous in nature to the bare Pt(II) aqua ion. A qualitative prediction on the kinetics of ligand exchange in oxaliplatin is derived based on its axial hydration pattern.

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Section: Introductionmentioning

confidence: 70%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Characterizing Pt‐Derived Anticancer Drugs from First Principles: The Case of Oxaliplatin in Aqueous Solution

Beret¹,

Pappalardo²,

Marx³

et al. 2009

ChemPhysChem

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“…The interface provided by CRYSTALFF significantly simplified this process. Other examples can be found in the literature (Curis et al, 2001;Van Koningsbruggen et al, 2000).…”

Section: Research Papersmentioning

confidence: 99%

CRYSTALFF– from crystallography to EXAFS multiple-scattering calculations withFEFF

Provost¹,

Champloy²,

Michalowicz³

2001

J Synchrotron Radiat

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“…17,18 The EX-AFS spectrum of oxaliplatin as well as of several parent drugs and their degradation products have been previously recorded and analyzed by some of our group. 19 In addition, we performed a Car-Parrinello molecular dynamics (CP-MD) simulation of ethyldiamineoxalatoplatinum(II) (EDO-Pt), a model structure for oxaliplatin obtained by removal of the outer part of the cyclohexane ring ( Fig. 1), in water.…”

Section: Introductionmentioning

confidence: 99%

EXAFS Debye-Waller factors issued from Car-Parrinello molecular dynamics: Application to the fit of oxaliplatin and derivatives

Provost

Beret

Müller

et al. 2013

The Journal of Chemical Physics

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One of the main pitfalls in EXAFS fitting is correlation among parameters, which can lead to unreliable fits. The use of theoretical Debye-Waller factors (DWs) is a promising way to reduce the number of fitted parameters. When working with molecular dynamics, it is not only possible to evaluate DWs from the statistical distributions issued from the trajectory but also to estimate the distribution anharmonicity, and to compute simulated average EXAFS spectra that can be fitted as experimental ones, in order to assess the ability of EXAFS fitting to recover information on DWs, as well as other structural and spectroscopical parameters. The case studied is oxaliplatin, a third generation anticancer drug. The structural information and the simulated average spectra were derived from a Car-Parrinello molecular dynamics (CP-MD) trajectory of a compound closely related to oxaliplatin. We present the DWs issued from this simulation and their use, by taking their theoretical absolute values (no DW fitted) or their ratios (one DW fitted). In this second approach, the fit of oxaliplatin experimental spectra leads to DWs values very close to the theoretical ones. This shows that the CP-MD trajectory provides a good representation of the distance distributions for oxaliplatin. Transferability of oxaliplatin DWs, for all relevant single and multiple scattering paths, to closely related compounds is proven for the case of bis(oxalato)platinum(II) and bis(ethylene diamine)platinum(II).

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Carboplatin and oxaliplatin decomposition in chloride medium, monitored by XAS

Abstract: The stability of carboplatin and oxaliplatin aqueous solutions has been studied under different chloride ions concentration and pH conditions. For both compounds, we demonstrate the chloration of the platinum first coordination shell.

Cited by 27 publications

References 12 publications

Characterizing Pt‐Derived Anticancer Drugs from First Principles: The Case of Oxaliplatin in Aqueous Solution

Characterizing Pt‐Derived Anticancer Drugs from First Principles: The Case of Oxaliplatin in Aqueous Solution

CRYSTALFF– from crystallography to EXAFS multiple-scattering calculations withFEFF

EXAFS Debye-Waller factors issued from Car-Parrinello molecular dynamics: Application to the fit of oxaliplatin and derivatives

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