Cisplatin cytotoxicity: a theoretical study of induced mutations

Cerón‐Carrasco, José P.; Jacquemin, Denis; Cauët, Émilie

doi:10.1039/c2cp40515f

Cited by 40 publications

(36 citation statements)

References 91 publications

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“…[70][71][72] It seems that the density functional theory model used in this paper is reliable. In addition, the obtained lengths have the difference within 0.001 Å by comparing with those reported by Schaefer et al [57] and Cerón-Carrasco et al, [73] which indicates the structure of A·U base pair is reasonable in this paper.…”

Section: Resultssupporting

confidence: 83%

DFT study of adenine‐uracil base pair damage by OH radical

Liao

Ling

et al. 2015

J of Physical Organic Chem

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The hydrogen abstraction and addition reactions of OH radical with A·U base pair have been explored by using density functional theory (DFT) both in gas phase and in aqueous solution. Solvent effects were taken into consideration by using the polarized continuum model. All the reaction pathways are exothermic in energy, and the compounds in aqueous phase are more favorable than those in gas phase. The relative free energies of adducts in the addition reaction are lower than those obtained for products in hydrogen abstraction reaction. Among dehydrogenation reaction, the hydrogen abstractions from AC2·U and AN6·U sites are more favorable than those from AC8·U, A·UC5, and A·UC6 sites. In addition, hydroxylation at AC8·U, A·UC5, and A·UC6 sites are more probable than other investigated positions. The hydroxylation at AH8·U site is most favorable, and hydroxylation at A·UC5 site is more preference than that at A·UC6 site controlled by the kinetics factors. The data in both gas phase and water solution demonstrated that addition of OH radical to A·UC5 and A·UC6 sites are more thermodynamically and kinetically favorable than abstracting the hydrogen atom form A·UC5 and A·UC6 sites. The phenomena are in agreement with the experimental observations. Copyright © 2015 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 83%

DFT study of adenine‐uracil base pair damage by OH radical

Liao

Ling

et al. 2015

J of Physical Organic Chem

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“…In fact, the less stable A‐T tautomers can also be implicated in biological phenomena if these are sufficiently fast, that is, of the same order of time as this unstable structure. In these studies on the G‐C base pair, the energetic and structural changes of this base pair due to Pt complex binding,13–15 the properties of their radical anions16, 17 and cations,18 and the mutual relationship between stacking and hydrogen bonding through complete DFT optimisation19 have been investigated. The results show that the metal complex binding induces a single‐proton transfer reaction13–15 with the hydrogen bond in O(G)–HN(C) lengthened (stronger), whereas the other hydrogen bonds are shortened (weaker) 13.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of the Coupling between Hydrogen‐Atom Transfer and Stacking Interaction in Adenine–Thymine Dimers

Villani¹

2013

ChemPhysChem

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Three different dimers of the adenine-thymine (A-T) base pair are studied to point out the changes of important properties (structure, atomic charge, energy and so on) induced by coupling between the movement of the atoms in the hydrogen bonds and the stacking interaction. The comparison of these results with those for the A-T monomer system explains the role of the stacking interaction in the hydrogen-atom transfer in this biologically important base pair. The results support the idea that this coupling depends on the exact dimer considered and is different for the N-N and N-O hydrogen bonds. In particular, the correlation between the hydrogen transfer and the stacking interaction is more relevant for the N-N bridge than for the N-O one. Also, the two different mechanisms of two-hydrogen transfer (step by step and concerted) can be modified by the stacking interaction between the base pairs.

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“…Although the intensity appears to depend on the molecular dimensions, a nearly linear correlation between the oscillator strength and the distance between the terminal atoms of the polyene chain, as found for the b-carotene isomers, [40] cannot be set up here. Proceeding to the absorption wavelengths, it is noteworthy that the s-cis rotamers tstt and tstst (see Figure 1 for labeling) are red-shifted with respect to ttt.…”

Section: Electronic Structures and Vertical Excitation Energiesmentioning

confidence: 87%

On the Photophysics of 1,6‐Diphenyl‐1,3,5‐Hexatriene Isomers and Rotamers

et al. 2011

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Herein, the low-lying electronic states of various isomers and rotamers of 1,6-diphenyl-1,3,5-hexatriene (DPH) are studied by a combination of density functional theory and multireference configuration interaction. Starting from the all-trans nuclear arrangement, trans-cis isomerization pathways in the electronic ground state and in the first excited triplet state were determined. Further, spin-orbit coupling calculations were carried out at selected points where singlet-triplet energy gaps are small. The calculations reveal that the primarily excited, optically bright 1(1)B(u) state undergoes a curve crossing with the optically dark multiconfigurational 2(1)A(g) state upon geometry relaxation in the excited state. The strong vibronic coupling of the two singlets in the neighborhood of the conical intersection provides a conclusive explanation for the experimentally observed fast equilibration of the states and the appearance of delayed fluorescence. With regard to the trans-cis isomerization of the central CC bond, the perpendicular conformation is found to represent a maximum on the energy profile not only of the electronic ground state, but also of the low-lying excited states. The lack of a strong driving force along the torsional coordinate explains the low tendency of DPH for isomerization. Finally, the results of our spin-orbit coupling calculations suggest that the intramolecular formation of DPH molecules in the T(1)(1(3)B(u)) state proceeds from the 1(1)B(u) state and involves intermediately the T(2)(1(3)A(g)) state.

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Cisplatin cytotoxicity: a theoretical study of induced mutations

Cited by 40 publications

References 91 publications

DFT study of adenine‐uracil base pair damage by OH radical

DFT study of adenine‐uracil base pair damage by OH radical

Theoretical Investigation of the Coupling between Hydrogen‐Atom Transfer and Stacking Interaction in Adenine–Thymine Dimers

On the Photophysics of 1,6‐Diphenyl‐1,3,5‐Hexatriene Isomers and Rotamers

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