Glycosaminoglycans are potential pharmacological targets for classic DNA minor groove binder drugs berenil and pentamidine

Literature Information

Publication Date 2015-08-26
DOI 10.1039/C5CP03153B
Impact Factor 3.676
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Abstract

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 (Ka ∼ 106 M−1 for berenil) and a lower (Ka ∼ 105 M−1 for pentamidine) affinity heparin binding of these agents, similar to that reported for DNA. Drug–chondroitin sulfate complexes (Ka ∼ 104–105 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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Front cover

Cover

DOI: 10.1039/C9QO90073J

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