Peptide nucleic acid containing a meta-substituted phenylpyrrolocytosine exhibits a fluorescence response and increased binding affinity toward RNA.
Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Filip
F
Wojciechowski
Robert H E
RH
Hudson
D003596:Cytosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000378:metabolism; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis* / Q000737:chemistry; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D012313:RNA / Q000378:metabolism; D013237:Stereoisomerism
D005456:Fluorescent Dyes; D016376:Oligonucleotides, Antisense; D020135:Peptide Nucleic Acids; D012313:RNA; D003596:Cytosine; D004247:DNA