Synthesis and characterization of pi-stacked phenothiazine-labeled oligodeoxynucleotides

S A Nadeem Hashmi; Xi Hu; Chad E Immoos; Stephen J Lee; Mark W Grinstaff

doi:10.1021/ol026704q

Synthesis and characterization of pi-stacked phenothiazine-labeled oligodeoxynucleotides

Org Lett. 2002 Dec 26;4(26):4571-4. doi: 10.1021/ol026704q.

Authors

S A Nadeem Hashmi¹, Xi Hu, Chad E Immoos, Stephen J Lee, Mark W Grinstaff

Affiliation

¹ Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708, USA.

PMID: 12489932
DOI: 10.1021/ol026704q

Abstract

[reaction: see text] A facile procedure for the incorporation of N-methyl phenothiazine as the terminal nucleoside in oligodeoxynucleotides is reported. The phenothiazine nucleoside analogue is synthesized and then incorporated into DNA using an automated DNA solid-phase synthesizer. Phenothiazine-labeled oligodeoxynucleotides form stable B-form duplexes with higher melting temperatures compared to unlabeled DNA duplexes.

Publication types

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

MeSH terms

Combinatorial Chemistry Techniques / instrumentation
Drug Stability
Electrons
Nucleic Acid Denaturation
Oligodeoxyribonucleotides / chemical synthesis*
Oligodeoxyribonucleotides / chemistry
Phenothiazines / chemistry*
Spectrum Analysis
Temperature

Substances

Oligodeoxyribonucleotides
Phenothiazines
N-methylphenothiazine