Abstract:
:The antitumor antibiotic CC-1065 binds in the minor groove of double-stranded DNA, and the cyclopropapyrroloindole (CPI) subunit of the drug alkylates adjacent adenines at their N-3 position. We have attached racemic CPI to oligodeoxyribonucleotides (ODNs) via a terminal phosphorothioate at either the 3'- or 5'-end of the ODNs. These conjugates were remarkably stable in aqueous solution at neutral pH even in the presence of strong nucleophiles. When a 3'-CPI-ODN conjugate was hybridized to a complementary DNA strand at 37 degrees C, the CPI moiety alkylated nearby adenine bases of the complement efficiently and rapidly, with a half-life of a few minutes. The 4'-CPR- ODN conjugate showed very little reactivity within the duplex. CPI-ODN conjugates should be highly effective sequence-specific inhibitors of single-stranded viral DNA replication or gene selective inhibitors of transcription initiation.
journal_name
Nucleic Acids Resjournal_title
Nucleic acids researchauthors
Lukhtanov EA,Podyminogin MA,Kutyavin IV,Meyer RB,Gamper HBdoi
10.1093/nar/24.4.683subject
Has Abstractpub_date
1996-02-15 00:00:00pages
683-7issue
4eissn
0305-1048issn
1362-4962pii
5j0636journal_volume
24pub_type
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journal_title:Nucleic acids research
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