DC Field | Value | Language |
---|---|---|
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Friesner, RA | ko |
dc.contributor.author | Lippard, SJ | ko |
dc.date.accessioned | 2016-04-12T07:47:51Z | - |
dc.date.available | 2016-04-12T07:47:51Z | - |
dc.date.created | 2015-09-11 | - |
dc.date.created | 2015-09-11 | - |
dc.date.issued | 2002-04 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.124, no.16, pp.4495 - 4503 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/203373 | - |
dc.description.abstract | The depurination reaction of guanosine, protonated or modified with cisplatin at the N7 position, has been studied by density functional theory (DFT), coupled with a continuum treatment of solvation. Protonation accelerates the depurination reaction whereas N7-platination, the initial product of cisplatin binding to DNA, does not. The computed reaction energy profiles demonstrate that N7-platination has only a minor effect on the energetics of the transition state, whereas protonation lowers it by similar to10 kcal mol(-1). The orbitals involved in N7-Pt/H bonding are examined, and electronic differences between the two substituted guanines are identified. Natural bond orbital analysis, fragment orbital analysis, and extended transition-state theory reveal how the electronically different substituents at the N7 position control the stability of the N9-C1' bond. The detailed description of the electronic structure of the N7-substituted guanosines and the computational protocol developed to obtain a realistic model for these systems not only explain a longstanding enigma but also provide guidelines for further studies toward understanding the interactions of cisplatin with DNA. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | EFFECTIVE CORE POTENTIALS | - |
dc.subject | TRANSITION-STATE METHOD | - |
dc.subject | REGULAR 2-COMPONENT HAMILTONIANS | - |
dc.subject | CONTINUUM DIELECTRIC THEORY | - |
dc.subject | ANTICANCER DRUG CISPLATIN | - |
dc.subject | DENSITY-FUNCTIONAL THEORY | - |
dc.subject | INTRASTRAND CROSS-LINK | - |
dc.subject | BASE-EXCISION REPAIR | - |
dc.subject | MOLECULAR CALCULATIONS | - |
dc.subject | AB-INITIO | - |
dc.title | Theoretical study on the stability of N-glycosyl bonds: Why does N7-platination not promote depurination? | - |
dc.type | Article | - |
dc.identifier.wosid | 000175088600061 | - |
dc.identifier.scopusid | 2-s2.0-0037165749 | - |
dc.type.rims | ART | - |
dc.citation.volume | 124 | - |
dc.citation.issue | 16 | - |
dc.citation.beginningpage | 4495 | - |
dc.citation.endingpage | 4503 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/ja017588+ | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Friesner, RA | - |
dc.contributor.nonIdAuthor | Lippard, SJ | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | EFFECTIVE CORE POTENTIALS | - |
dc.subject.keywordPlus | TRANSITION-STATE METHOD | - |
dc.subject.keywordPlus | REGULAR 2-COMPONENT HAMILTONIANS | - |
dc.subject.keywordPlus | CONTINUUM DIELECTRIC THEORY | - |
dc.subject.keywordPlus | ANTICANCER DRUG CISPLATIN | - |
dc.subject.keywordPlus | DENSITY-FUNCTIONAL THEORY | - |
dc.subject.keywordPlus | INTRASTRAND CROSS-LINK | - |
dc.subject.keywordPlus | BASE-EXCISION REPAIR | - |
dc.subject.keywordPlus | MOLECULAR CALCULATIONS | - |
dc.subject.keywordPlus | AB-INITIO | - |
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