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Thiazole orange-peptide conjugates: sensitivity of DNA binding to chemical structure.

Authors
  • Carreon, Jay R
  • Mahon, Kerry P Jr
  • Kelley, Shana O
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Feb 19, 2004
Volume
6
Issue
4
Pages
517–519
Identifiers
PMID: 14961612
Source
Medline
License
Unknown

Abstract

[structure: see text] Derivatives of the highly fluorescent and DNA-binding dye thiazole orange (TO) are described that feature appended peptides. Functionalization of TO can be achieved at either of the endocyclic nitrogens, and the photophysical properties and DNA-binding modes are sensitive to the position of the tethered peptide. A series of TO-peptide conjugates are described, demonstrating the utility of a solid-phase synthesis approach to their preparation and illustrating how the photophysical and DNA-binding properties of the compounds are influenced by chemical structure.

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