PMID: 8604317Feb 15, 1996Paper

Triplex formation by a psoralen-conjugated oligodeoxyribonucleotide containing the base analog 8-oxo-adenine

Nucleic Acids Research
P S MillerR K DeLong

Abstract

Oligodeoxyribonucleotides containing thymidine and 8-oxo-2'-deoxyadenosine can form pyr.pur.pyr type triplexes with double-stranded DNA. Unlike triplexes whose third strands contain thymidine and deoxycytidine, the stability of these triplexes is independent of pH. We have prepared d-ps-TAAATAAATTTTTAT-L [I(A)], where A is 8-oxo-2'-deoxyadenosine, ps is 4'-hydroxymethyl-4,5',8- trimethylpsoralen and L is a 6-amino-2-(hydroxymethyl)hexyl linker. The oligomer is designed to interact with a homopurine sequence in the promoter region of the human gene coding for the 92 kDa form of collagenase type IV. Oligomer I(A) and oligomer I(C), which contains 2'-deoxycytidine in place of 8-oxo-2'-deoxycytidine, both form stable triplexes at pH 6.2, but only I(A) forms a stable triplex with a model duplex DNA target at pH 7.5, as determined by UV melting experiments. Triplex formation is stabilized by the presence of the psoralen group. Upon irradiation both I(A) and I(C) form photoadducts with the DNA target at pH 6.2, but only I(A) forms a photoadduct at pH 7.5. In these photoreactions oligomer I(A) appears to selectively form a photoadduct with a C in the purine-rich strand of the duplex target. Although a T residue is present in the pyrimi...Continue Reading

References

May 1, 1992·Proceedings of the National Academy of Sciences of the United States of America·S H KrawczykM D Matteucci
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Nov 15, 1991·Proceedings of the National Academy of Sciences of the United States of America·S L YoungJ J Toole
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Citations

Dec 25, 2007·Oligonucleotides·Zhaoyang YeRam I Mahato
Jul 11, 2003·Nucleic Acids Research·Rachel A CassidyPaul S Miller
Apr 2, 2004·Biological & Pharmaceutical Bulletin·Fumi Nagatsugi, Shigeki Sasaki
Mar 29, 2000·Proceedings of the National Academy of Sciences of the United States of America·J E RaoN L Craig
Aug 20, 2003·The Journal of Clinical Investigation·Michael M Seidman, Peter M Glazer
Mar 13, 2019·Current Protocols in Nucleic Acid Chemistry·Ken YamadaFumi Nagatsugi
Jul 18, 2018·The Journal of Organic Chemistry·Ken YamadaFumi Nagatsugi

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