Two novel microgonotropens (MGTs) comprised of hairpin N-propylaminepyrrole polyamides linked to a Hoechst 33258 (Ht) analogue (3 and 4) were synthesized on solid phase by adopting an Fmoc technique using a series of HOBt mediated coupling reactions. The dsDNA-binding properties of MGTs 3 and 4 were determined by thermal denaturation experiments. Both MGTs were found to be selective for their nine-bp match dsDNA sequence 9 and were less tolerant of G/C bp substitutions in the binding region than linear progenitor MGT 1. MGT 3 was intolerant of a G/C substitution located in the middle of the binding region and did not bind to sequences 13 and 14. MGT 4 also did not bind to sequence 13, and its linker-bound Ht moiety was found to be more sensitive to a G/C substitution in the Ht-binding target, as demonstrated by the lack of binding to sequence 16. © 2006 Elsevier Ltd. All rights reserved.
CITATION STYLE
Kahane, A. L., & Bruice, T. C. (2006). DNA sequence recognition in the minor groove by hairpin microgonotropens. Bioorganic and Medicinal Chemistry Letters, 16(24), 6255–6261. https://doi.org/10.1016/j.bmcl.2006.09.032
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