Table · dataset · 2026
Multifaceted Computational Analysis of O<sup>6</sup>‑Methylguanine and O<sup>6</sup>‑Methylthioguanine Nucleobase Complexes
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Improper DNA methylation yields <i>O</i><sup>6</sup>-methylguanine, which induces GC-AT mutations if left unchecked by <i>O</i><sup>6</sup>-methylguanine DNA methyltransferase (MGMT).
Description
Previous ab initio studies have computed the interaction energy of <i>O</i><sup>6</sup>-methylguanine with cytosine and thymine, but this study probes deeper by investigating the noncovalent interactions through various forms of energy decomposition analysis.
The same methods are then applied to the sulfur analog of <i>O</i><sup>6</sup>-methylguanine, <i>S</i><sup>6</sup>-methylthioguanine, which is likewise highly mutagenic but has received considerably less computational treatment. Interaction energies computed at the ωB97X-D3/aug-cc-pVTZ and SAPT2+/aug-cc-pVDZ levels of theory revealed that <i>O</i><sup>6</sup>-methylguanine and <i>S</i><sup>6</sup>-methylthioguanine form substantially weaker complexes than the unmethylated G:C and TG:C pairs yet may continue to prefer binding to cytosine over thymine.
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NCI and NBO analyses demonstrated that the <i>O</i><sup>6</sup>-methylguanine and <i>S</i><sup>6</sup>-methylthioguanine complexes with cytosine or thymine are driven primarily by two hydrogen bonds, which are noticeably weaker than the average hydrogen bond observed among the canonical base pairs. The molecular electrostatic potential (MEP) of these nucleobases likewise predicted that the exocyclic amine on <i>O</i><sup>6</sup>-methylguanine and <i>S</i><sup>6</sup>-methylthioguanine is less electrophilic than the H-bond donors on guanine and thioguanine.
In direct comparison to <i>O</i><sup>6</sup>-methylguanine, the <i>S</i><sup>6</sup>-methylthioguanine complexes are qualitatively similar but exhibit weaker hydrogen bonding and greater dispersion forces.
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Where it is published
- DOI doi.org/10.1021/acs.jpcb.6c04517.s001 ↗
DOI / persistent id · from figshare com
Catalogue records · 1
- OAI-PMH record api.figshare.com/v2/oai?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Af… ↗
metadata API · from figshare com
Topics
Provenance · 1 source records, 19 field assertions
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|---|---|---|---|
| figshare | oai:figshare.com:article/33954486 | 10 d ago | JSON v1 |
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| title | source · figshare com | connector:figshare_com@1.0.0 | /metadata/dc/title |