Synthesis and characterization of pi-stacked phenothiazine-labeled oligodeoxynucleotides.
[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.
Hashmi
S A Nadeem
SA
Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708, USA.
Hu
Xi
X
Immoos
Chad E
CE
Lee
Stephen J
SJ
Grinstaff
Mark W
MW
D020650:Combinatorial Chemistry Techniques / Q000295:instrumentation; D004355:Drug Stability; D004583:Electrons; D009691:Nucleic Acid Denaturation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010640:Phenothiazines / Q000737:chemistry*; D013057:Spectrum Analysis; D013696:Temperature
D009838:Oligodeoxyribonucleotides; D010640:Phenothiazines; C045775:N-methylphenothiazine