Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 17, Issue 38, Pages 24560-24565Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cp03153b
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It is shown that the antiprotozoal drugs berenil and pentamidine, conventional minor groove binders of DNA, form non-covalent complexes with polyanionic glycosaminoglycans. Induced circular dichroism (CD) spectra as well as UV hypochromism confirmed drug binding to the asymmetric template of heparin and chondroitin 6-sulfate. The biphasic nature of the CD signals refers to intermolecular chiral exciton coupling between the dicationic guest molecules forming a right-or a left-handed helical array along the GAG chains. Quantitative evaluation of the spectroscopic data measured in pH 7.0 buffer solution (80 mM NaCl) indicated a higher (K-a similar to 10(6) M-1 for berenil) and a lower (K-a similar to 10(5) M-1 for pentamidine) affinity heparin binding of these agents, similar to that reported for DNA. Drug-chondroitin sulfate complexes (K-a similar to 10(4)-10(5) M-1) could be detected only at low ionic strength. These results imply that besides nucleic acids, GAGs may be another pharmacological targets for diarylamidine drugs.
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