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Base pairing patterns of DNA base lesion spiroiminodihydantoin: A DFT study
Author(s) -
Shukla Pradeep Kumar,
Mishra P.C.
Publication year - 2013
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.24512
Subject(s) - guanine , thymine , cytosine , nucleic acid , dna , base pair , chemistry , base (topology) , pairing , nucleobase , basis set , stereochemistry , density functional theory , biochemistry , computational chemistry , crystallography , nucleotide , gene , physics , mathematics , quantum mechanics , mathematical analysis , superconductivity
The DNA base lesion spiroiminodihydantoin ( Sp ) is produced in biological systems endogenously and can cause mutation and cancer. It is considered to be more mutagenic and deleterious than 8‐oxoguanine and other oxidized guanine products such as guanidinohydantoin ( Gh ) and imidazolone. In this work, the base pairing patterns of Sp with each of the normal nucleic acid bases of DNA have been investigated thoroughly using the B3LYP, M06‐2X, and wB97X‐D functionals of density functional theory in conjunction with the aug‐cc‐pVDZ basis set. It is found that the magnitudes of interaction energies between the bases and Sp follow the order: Sp ‐guanine >> Sp ‐cytosine > Sp ‐adenine > Sp ‐thymine. The strong Sp ‐guanine abnormal base pairing may be the main cause of the observed mutagenicity of Sp . © 2013 Wiley Periodicals, Inc.