DNA Binding and Recognition of a CC Mismatch in a DNA Duplex by Water-Soluble Peptidocalix[4]arenes: Synthesis and Applications

Nahid S Alavijeh; Reza Zadmard; Saeed Balalaie; Mohammad S Alavijeh; Nima Soltani

doi:10.1021/acs.orglett.6b01995

DNA Binding and Recognition of a CC Mismatch in a DNA Duplex by Water-Soluble Peptidocalix[4]arenes: Synthesis and Applications

Org Lett. 2016 Oct 7;18(19):4766-4769. doi: 10.1021/acs.orglett.6b01995. Epub 2016 Sep 15.

Authors

Nahid S Alavijeh¹, Reza Zadmard¹, Saeed Balalaie², Mohammad S Alavijeh³, Nima Soltani⁴

Affiliations

¹ Chemistry and Chemical Engineering Research Center of Iran , P.O. Box 14335-186, Tehran 1496813151, Iran.
² Peptide Chemistry Research Center, K.N. Toosi University of Technology , P.O. Box 15875-4416, Tehran 1969764499, Iran.
³ Pharmidex Pharmaceutical Services, Limited, London W1S 1YH, U.K.
⁴ Department of Chemistry, Sharif University of Technology , P.O. Box 11155-3516, Tehran 1458889694, Iran.

PMID: 27631139
DOI: 10.1021/acs.orglett.6b01995

Abstract

Water-soluble peptidocalix[4]arenes were synthesized by the introduction of arginine-rich narrow groove-binding residues at lower rims through solid-phase synthesis. The study of binding of these water-soluble bidentate ligands to well-matched and mismatched DNA duplexes by fluorescent titrations, ethidium bromide (EB) displacement assays, DNA-melting experiments, and circular dichroism (CD) analysis revealed a sequence-dependent groove-binding mechanism.

Publication types

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

MeSH terms

Base Composition
Base Pair Mismatch*
Base Sequence
Binding Sites
Calixarenes / chemical synthesis*
Calixarenes / chemistry
Circular Dichroism
Cytosine / chemistry*
DNA / chemistry*
Ligands
Models, Molecular
Molecular Structure
Nucleic Acid Conformation*
Oligopeptides / chemical synthesis*
Oligopeptides / chemistry
Solubility
Water / chemistry

Substances

Ligands
Oligopeptides
Water
Calixarenes
Cytosine
DNA