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Alkylation of a human telomere sequence by heterotrimeric chlorambucil PI polyamide conjugates
We designed and synthesized human telomere alkylating N-methylpyrrole-N-methylimidazole (PI) polyamide conjugates (1-6). The C-type conjugates 1-3 possessed a chlorambucil moiety at the C terminus, whereas the N-type conjugates 4-6 had one of these moieties at the N terminus. The DNA alkylating activity of these conjugates was evaluated by high-resolution denaturing polyacrylamide gel electrophoresis using a 220 bp DNA fragment containing the human telomere repeat sequence 5?-(GGGTTA)4-3?/5?-(TAACCC)4-3?. C-type conjugates are designed to alkylate the G-rich-strand-containing 5?-GGGTTA-3? and N-type conjugates were designed to alkylate the complementary C-rich strand-containing 5?-TAACCC-3? sequence. The difference between conjugates 1-3 and 4-6 lies in the linker region between the polyamide moiety and chlorambucil. Conjugates 1 and 4 efficiently alkylated the 5?-GGTTAGGGTTA-3? and 5?-CCCTAACCCTAA-3? sequences, respectively, by recognizing 11 bp in the presence of distamycin A (Dist), in a heterotrimeric manner: one long alkylating polyamide conjugate (1-6) and two short partners (Dist).
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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI