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Capillary zone electrophoretic studies of interactions of some quaternary isoquinoline alkaloids with DNA constituents and DNA
Author(s) -
Vlčková Markéta,
Kubán Vlastimil,
Vičar Jaroslav,
Šimánek Vilím
Publication year - 2005
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.200410193
Subject(s) - sanguinarine , isoquinoline , chemistry , phenanthridine , berberine , dna , ethidium bromide , chelerythrine , nucleobase , capillary electrophoresis , tetramer , intermolecular force , stereochemistry , non covalent interactions , electrophoresis , chromatography , alkaloid , biochemistry , hydrogen bond , organic chemistry , molecule , protein kinase c , enzyme
Capillary zone electrophoresis was applied for the investigation of interactions of some quaternary isoquinoline alkaloids, namely sanguinarine, chelerythrine, berberine, and jatrorrhizine, with DNA constituents and with DNA. None of these alkaloids attach covalently to nucleotides or to the whole DNA under physiological conditions. The interaction with DNA constituents is a noncovalent complexation based on weak intermolecular forces. Electrostatic attraction participates in the interaction but other types of intermolecular forces are involved as well. Cations were identified as the most probable interacting forms of the alkaloids. The interaction with compounds derived from purine was always stronger than those derived from pyrimidine. All alkaloids behaved analogously and similarly to ethidium bromide, the classic DNA intercalator. Stability constants K (in l·mol −1 ) for sanguinarine and chelerythrine in phosphate buffer of pH 7.4 ( I S = 30 m M ) ranged from tens to hundreds.