Synthesis of oligodeoxynucleotides containing a single diastereoisomer of alpha-(N2-2'-deoxyguanosinyl)-N-desmethyltamoxifen

Y R Santosh Laxmi; Naomi Suzuki; Sung Yeon Kim; Shinya Shibutani

doi:10.1016/j.bmcl.2004.05.030

Synthesis of oligodeoxynucleotides containing a single diastereoisomer of alpha-(N2-2'-deoxyguanosinyl)-N-desmethyltamoxifen

Bioorg Med Chem Lett. 2004 Aug 2;14(15):4051-4. doi: 10.1016/j.bmcl.2004.05.030.

Authors

Y R Santosh Laxmi¹, Naomi Suzuki, Sung Yeon Kim, Shinya Shibutani

Affiliation

¹ Laboratory of Chemical Biology, Department of Pharmacological Sciences, State University of New York at Stony Brook, Stony Brook, New York 11794-8651, USA.

PMID: 15225724
DOI: 10.1016/j.bmcl.2004.05.030

Abstract

A phosphoramidite chemical synthesis of oligodeoxynucleotides containing a diastereoisomer of (E)-alpha-(N(2)-deoxyguanosinyl)-N-desmethyltamoxifen, a major tamoxifen (TAM)-derived DNA adduct in animal and women treated with TAM, was described. The site-specifically modified oligodeoxynucleotide can be used for mutagenesis, DNA repair, and 3D structural studies and also as standard for quantitative analysis of TAM-DNA adducts in animal and human.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Animals
Base Sequence
Chromatography, High Pressure Liquid
DNA Adducts
Deoxyguanosine
Humans
Molecular Conformation
Oligodeoxyribonucleotides / chemical synthesis*
Oligodeoxyribonucleotides / pharmacology*
Stereoisomerism
Tamoxifen / analogs & derivatives*
Tamoxifen / chemical synthesis*
Tamoxifen / pharmacology

Substances

DNA Adducts
Oligodeoxyribonucleotides
Tamoxifen
Deoxyguanosine

Grants and funding

ES 09418/ES/NIEHS NIH HHS/United States