Molecular recognition of pyrimidine nucleobases by triplex DNA receptors

Zixing Zhuang; Rui Pan; Qian Zhang; Haidong Huang

doi:10.1016/j.bmcl.2015.02.019

Molecular recognition of pyrimidine nucleobases by triplex DNA receptors

Bioorg Med Chem Lett. 2015 Apr 1;25(7):1520-4. doi: 10.1016/j.bmcl.2015.02.019. Epub 2015 Feb 18.

Authors

Zixing Zhuang¹, Rui Pan¹, Qian Zhang¹, Haidong Huang²

Affiliations

¹ Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, NJ 07102, United States.
² Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, NJ 07102, United States. Electronic address: haidong.huang@njit.edu.

PMID: 25740158
DOI: 10.1016/j.bmcl.2015.02.019

Abstract

Triplex DNA receptors are known for their strong and specific binding of a variety of purine ligands. However, not many studies have been reported on their binding of pyrimidine ligands. Here we used fluorophore-labeled DNA receptors to study these binding interactions. The results suggest that in general, cytosine binds more strongly than thymine and uracil, although the selectivity between two pyrimidine ligands can be tuned by changing the surrounding nucleobases of the DNA receptor. In contrast, binding of pyrimidine nucleosides is much weaker, possibly due to lack of the N1 hydrogen bonding donor.

Keywords: Binding; DNA receptors; Fluorescence.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding Sites / drug effects
DNA / chemistry*
Hydrogen Bonding
Ligands
Nucleic Acid Conformation
Pyrimidines / chemistry*
Receptors, Cell Surface / chemistry*

Substances

DNA receptor
Ligands
Pyrimidines
Receptors, Cell Surface
triplex DNA
DNA