Interactions of Ascorbic Acid with Satraplatin and its trans Analog JM576: DFT Computational Study
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F18%3A10384675" target="_blank" >RIV/00216208:11320/18:10384675 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/ejic.201701334" target="_blank" >https://doi.org/10.1002/ejic.201701334</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejic.201701334" target="_blank" >10.1002/ejic.201701334</a>
Alternative languages
Result language
angličtina
Original language name
Interactions of Ascorbic Acid with Satraplatin and its trans Analog JM576: DFT Computational Study
Original language description
Knowledge of the mechanisms for the reduction of Pt-IV anticancer prodrugs is of great importance, since the reduction process is considered as a necessary step for their activation. Therefore, in this study, we investigate the reduction of satraplatin {JM216, cis,trans,cis-[PtCl2(OAc)(2)(cha)(NH3)], cha = cyclohexylamine} by ascorbic acid (AA) where proton-assisted electron-transfer and outer-sphere electron-transfer mechanisms are employed. Also, the presence of an additional base, which should increase the concentration of the deprotonated AA(2-) form, is discussed. Structures are optimized at the B3LYP-GD3BJ/6-31+G(d)/MWB60/C-PCM/Klamt level and single-point calculations are performed in the larger 6-311++G(2df,2pd)/MWB60 basis set, together with the better implicit solvation model - IEF-PCM/scaled-UAKS. All three protonation states of ascorbic acid are taken into consideration. An effective rate constant of 2.6x10(-3) m(-1)s(-1) is obtained from the kinetic formalism for side reactions, as described recently. For the reduction of satraplatin by fully deprotonated ascorbic acid, changes of the electron-density distribution along the reaction coordinate are further investigated using NPA, QTAIM, and reaction electronic-flux analysis. Both electron-transfer mechanisms are also explored for the satraplatin trans analog JM576 {trans,trans,trans-[PtCl2(OAc)(2)(cha)(NH3)]}. The resulting effective rate constant of 5.1x10(-2) m(-1)s(-1) is compared with available experimental data.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)
Result continuities
Project
<a href="/en/project/GA16-06240S" target="_blank" >GA16-06240S: Structure and dynamics of organometallic complexes in bio-environment.</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Inorganic Chemistry
ISSN
1434-1948
e-ISSN
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Volume of the periodical
2018
Issue of the periodical within the volume
13
Country of publishing house
DE - GERMANY
Number of pages
11
Pages from-to
1481-1491
UT code for WoS article
000430003700003
EID of the result in the Scopus database
2-s2.0-85042069732