Synthesis and DNA-binding Properties of 1,2,3-triazole-linked H-pin Pyrrole- and Imidazole-containing Polyamides Formed by the Huisgen Reaction
Document Type
Article
Publication Date
4-2012
Publication Source
Heterocyclic Communications
Volume Number
18
Issue Number
2
First Page
79
Last Page
85
Publisher
Walter de Gruyter & Co.
ISSN
0793-0283
E-ISSN
2191-0197
Abstract
Covalently linked pyrrole (Py)- and imidazole (Im)-containing H-pin polyamides bind in the minor groove of specific DNA sequences with high affinity. The synthesis of 1,2,3-triazole-linked and heterodimeric H-pin polyamides 13a,b formed from the Huisgen reaction of an alkyne-containing f-PyPyPy (6) with an azide-containing f-ImPyIm (7) is reported. The reaction proceeded smoothly under thermal conditions to give an inseparable mixture of 1,4- and 1,5-isomers (13a and 13b, respectively) by column chromatography. When the reaction was conducted under 'click' or Cu(I)-catalyzed conditions or in the presence of the cognate DNA sequence, no desired product was observed. Preliminary results from DNA thermal denaturation and circular dichroism titration studies provided evidence of mixture 13a, b binding to the target DNA sequence 5'-TCTCAA-3'.
Keywords
DNA; imidazoles; polyamides; pyrroles; sequence specifi city; 1, 2, 3-triazole
Recommended Citation
- Babu, Balaji, Kimberly A. Brien, Vijay Satam, Adam Plaunt, Mary Pressler, Hao Shen,
- Shannon Alger, Ross Ogilvie, Robert Sjoholm, Samuel Tzou, Olivia Sweat, Toni Rice, Hilary Mackay, Michael D. Seymour and Moses N. F. Lee. "Synthesis and Dna-Binding Properties of 1,2,3-Triazole-Linked H-Pin Pyrrole- and Imidazole-Containing Polyamides Formed by the Huisgen Reaction." Heterocyclic Communications 18, no. 2.00 (2012): 79-85. http://dx.doi.org/10.1515/hc-2012-0003
