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Use of a Coumarin-Labeled Hexa-Arginine Peptide as a Fluorescent Hydroxyl Radical Probe in a Nanoparticulate Plasmid DNA Condensate

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Department of Biochemistry, Mortensen Hall, Loma Linda University, 11085 Campus Street, Loma Linda, California 92350, United States
Department of Radiology, University of California at San Diego, 9500 Gilman Drive, La Jolla, California 92093-0610, United States
E-mail: [email protected]. Phone: 858-534-4919. Fax: 858-534-0265.
Cite this: J. Phys. Chem. B 2011, 115, 32, 9889–9897
Publication Date (Web):July 8, 2011
https://doi.org/10.1021/jp205198b
Copyright © 2011 American Chemical Society
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Abstract

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Coumarin derivatives have found application as probes for the hydroxyl radical because one of the products of the reaction between them is a highly fluorescent umbelliferone. We have examined the interaction in aqueous solution between a cationic coumarin-labeled hexa-arginine peptide ligand and plasmid DNA, and compared after gamma irradiation the yields of products derived from both of them. At low ionic strengths, the ligand binds very tightly to the plasmid. Compared with the structurally similar 4-methylumbelliferone (phenolic pKa = 7.8), the fluorescent product derived from gamma irradiation of the coumarin labeled cationic peptide is significantly more acidic (pKa = 6.1), making it a very convenient probe for solutions of pH in the physiological range. The yield of this product is generally in excellent agreement over a wide range of conditions with that of the single strand break product produced by the reaction of the hydroxyl radical with the plasmid. Thus coumarin-labeled peptide ligands offer promise as hydroxyl radical probes for locations in close proximity to DNA.

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