Abstract:
:A new intercalating nucleic acid monomer M comprising a 4-(1-indole)-butane-1,2-diol moiety was synthesized via a classical alkylation reaction of indole-3-carboxaldehyde followed by a condensation reaction with phenanthrene-9,10-dione in the presence of ammonium acetate to form a phenanthroimidazole moiety linked to the indole ring. Insertion of the new intercalator as a bulge into a Triplex Forming Oligonucleotide resulted in good thermal stability of the corresponding Hoogsteen-type triplexes. Molecular modeling supports the possible intercalating ability of M. Hybridisation properties of DNA/DNA and RNA/DNA three-way junctions (TWJ) with M in the branching point were also evaluated by their thermal stability at pH 7. DNA/DNA TWJ showed increase in thermal stability compared to wild type oligonucleotides whereas this was not the case for RNA/DNA TWJ.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Fatthalla MI,Elkholy YM,Abbas NS,Mandour AH,Jørgensen PT,Bomholt N,Pedersen EBdoi
10.1016/j.bmc.2011.11.013subject
Has Abstractpub_date
2012-01-01 00:00:00pages
207-14issue
1eissn
0968-0896issn
1464-3391pii
S0968-0896(11)00939-4journal_volume
20pub_type
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