A theoretical study of pyrimidine photohydrates and a proposed mechanism for the mutagenic effect of ultraviolet light

Danilov, V.I.; Stewart, James J. P.; Leś, Andrzej; Alderfer, James L.

doi:10.1016/s0009-2614(00)00909-x

Cited by 14 publications

(13 citation statements)

References 26 publications

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“…It is well recognized that prototropy in nucleobases influences the structure of nucleic acids and their replication, mutation, and degradation processes [1][2][3][4][5][6][7][8][9][10][11][12][13]. Labile hydrogens can move as protons between conjugated sites and change properties of nucleobases, particularly their ability to H-bonding.…”

Section: Introductionmentioning

confidence: 99%

“…When the tautomeric equilibrium for one base is disturbed, the pairing may be mismatched, and mutations of single nucleotide (point mutation) may appear [2,[9][10][11][12][13]. When the point mutation in some genes is followed by changes in the sequence of amino acids, the changes may lead to serious diseases, e.g., cystic fibrosis, mucosal melanoma, colorectal cancer, lung cancer, and pancreatic cancer.…”

Section: Introductionmentioning

confidence: 99%

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DFT studies on the favored and rare tautomers of neutral and redox cytosine

Raczyńska

Sapuła²,

Zientara‐Rytter³

et al. 2015

Struct Chem

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The complete tautomeric mixture consisting of nine prototropic tautomers has been studied in the gas phase at the DFT(B3LYP)/6-311?G(d,p) level for neutral, oxidized, and reduced cytosine. Rotational isomerism of the exo -OH group and geometrical isomerism of the exo =NH group have also been considered. Tautomeric conversions possible for cytosine have been compared with those for its structural models, 4-amino-and 2-hydroxypyrimidine. Effects of intramolecular interactions between neighboring groups for cytosine are analogous to those observed for model compounds. Although they are not very strong, they are sufficient to influence tautomeric equilibria and relative stabilities of individual tautomers. One-electron oxidation and one-electron reduction change tautomeric preferences. Tautomers that are rare forms for neutral cytosine become favored ones for oxidized and reduced cytosine. Aromaticity is not the main factor that dictates the tautomeric preferences. Stability of functional groups seems to be more important than full electron delocalization.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DFT studies on the favored and rare tautomers of neutral and redox cytosine

Raczyńska

Sapuła²,

Zientara‐Rytter³

et al. 2015

Struct Chem

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“…Blue light has been reported to be inherently mutagenic and is less effective for clinical PDT, as it is absorbed by endogenous chromophores and is strongly scattered by live tissue (resulting in lower penetration 165 depth). 44,45 Therefore red light (657 nm) was used throughout this study.…”

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confidence: 99%

One- and two-photon activated phototoxicity of conjugated porphyrin dimers with high two-photon absorption cross sections

et al. 2009

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“…The lower fidelity may have to do with the greater ability of an m C in a CPD to adopt the E-imino tautomer compared with an undamaged m C due to the loss of aromatic stabilization of the amino tautomer (27,29,30). Interestingly, we had observed a selectivity of only 120 for insertion opposite the m C in an m CϭT CPD (33), suggesting that the 5Ј-m C may be more prone to tautomerization or that insertion opposite the amino tautomer is less specific opposite the 5Ј-m C of a CPD.…”

Section: Discussionmentioning

confidence: 99%

“…Gas phase theoretical calculations have reproduced the preference for the imino tautomeric form in non-polar environments (29,30) but failed to reproduce the preference for the amino form in water (30). The same type of calculations also predicted that the Cs in CPD should exist almost exclusively in the imino tautomeric state in water (27).…”

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confidence: 99%