DNA triplex formation with 5-dimethylaminopropargyl deoxyuridine.
We have prepared triplex-forming oligonucleotides containing the nucleotide analogue 5-dimethylaminopropargyl deoxyuridine (DMAPdU) in place of thymidine and examined their ability to form intermolecular triple helices by thermal melting and DNase I footprinting studies. The results were compared with those for oligonucleotides containing 5-aminopropargyl-dU (APdU), 5-guanidinopropargyl-dU (GPdU) and 5-propynyl dU (PdU). We find that DMAPdU enhances triplex stability relative to T, though slightly less than the other analogues that bear positive charges (T << PdU < DMAPdU < APdU < GPdU). For oligonucleotides that contain multiple substitutions with DMAPdU dispersed residues are more effective than clustered combinations. DMAPdU will be especially useful as a nucleotide analogue as, unlike APdU and GPdU, the base does not require protection during oligonucleotide synthesis and it can therefore be used with other derivatives that require mild deprotection conditions.
Rusling
David A
DA
School of Biological Sciences, University of Southampton, Bassett Crescent East, Southampton SO16 7PX, UK.
Peng
Guomei
G
Srinivasan
Natarajan
N
Fox
Keith R
KR
Brown
Tom
T
D001483:Base Sequence; D004247:DNA / Q000737:chemistry*; D018983:DNA Footprinting; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry; D005453:Fluorescence; D007700:Kinetics; D008744:Methylamines / Q000737:chemistry*; D009691:Nucleic Acid Denaturation; D009841:Oligonucleotides / Q000737:chemistry
C527039:5-dimethylaminopropargyl deoxyuridine; D008744:Methylamines; D009841:Oligonucleotides; C051802:triplex DNA; D004247:DNA; D003857:Deoxyuridine