An ab initio mechanism for efficient population of triplet states in cytotoxic sulfur substituted DNA bases: the case of 6-thioguanine

被引：75

作者：

Martinez-Fernandez, Lara ^{[1
]}

Gonzalez, Leticia ^{[2
]}

Corral, Ines ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim, E-28049 Madrid, Spain

[2] Univ Vienna, Inst Theoret Chem, A-1090 Vienna, Austria

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 15期

关键词：

UVA LIGHT; THIOPURINES; LESIONS; DAMAGE; MODEL;

D O I：

10.1039/c2cc15775f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The deactivation mechanism of the cytotoxic 6-thioguanine, the 6-sulfur-substituted analogue of the canonical DNA base, is unveiled by ab initio calculations. Oxygen-by-sulfur substitution leads to efficient population of triplet states-the first step for generating singlet oxygen-which is responsible for its cytotoxicity.

引用

页码：2134 / 2136

页数：3

共 21 条

[1] Inherited variants of MYH associated with somatic G:C→T:A mutations in colorectal tumors [J].

Al-Tassan, N ;

Chmiel, NH ;

Maynard, J ;

Fleming, N ;

Livingston, AL ;

Williams, GT ;

Hodges, AK ;

Davies, DR ;

David, SS ;

Sampson, JR ;

Cheadle, JR .

NATURE GENETICS, 2002, 30 (02) :227-232

[2] Relaxation mechanisms of UV-photoexcited DNA and RNA nucleobases [J].

Barbatti, Mario ;

Aquino, Adelia J. A. ;

Szymczak, Jaroslaw J. ;

Nachtigallova, Dana ;

Hobza, Pavel ;

Lischka, Hans .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (50) :21453-21458

[3] Reactive oxygen species generated by thiopurine/UVA cause irreparable transcription-blocking DNA lesions [J].

Brem, Reto ;

Li, Feng ;

Karran, Peter .

NUCLEIC ACIDS RESEARCH, 2009, 37 (06) :1951-1961

[4] THE PURINE PATH TO CHEMOTHERAPY [J].

ELION, GB .

SCIENCE, 1989, 244 (4900) :41-47

[5] SPIN-ORBIT COUPLING AND RADIATIONLESS PROCESSES IN NITROGEN HETEROCYCLICS [J].

ELSAYED, MA .

JOURNAL OF CHEMICAL PHYSICS, 1963, 38 (12) :2834-&

[6] Medical progress - Skin cancers after organ transplantation [J].

Euvrard, S ;

Kanitakis, J ;

Claudy, A .

NEW ENGLAND JOURNAL OF MEDICINE, 2003, 348 (17) :1681-1691

[7] TDDFT STUDY OF NUCLEOBASE THIOANALOGUES AND OXO-DERIVATIVES EXCITED STATES [J].

Gomzi, Vjeran .

JOURNAL OF THEORETICAL & COMPUTATIONAL CHEMISTRY, 2009, 8 (01) :71-83

[8] Singlet-Triplet States Interaction Regions in DNA/RNA Nucleobase Hypersurfaces [J].

Gonzalez-Luque, Remedios ;

Climent, Teresa ;

Gonzalez-Ramirez, Israel ;

Merchan, Manuela ;

Serrano-Andres, Luis .

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2010, 6 (07) :2103-2114

[9]

Herzberg G., 1950, Molecular Spectra and molecular structure

[10] Thiopurines in current medical practice: molecular mechanisms and contributions to therapy-related cancer [J].

Karran, Peter ;

Attard, Natalie .

NATURE REVIEWS CANCER, 2008, 8 (01) :24-36

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