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Thymol and carvacrol binding to DNA: model for DRUG–DNA interaction
Author(s) -
Nafisi Sh.,
Hajiakhoondi A.,
Yektadoost A.
Publication year - 2004
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20080
Subject(s) - thymol , carvacrol , chemistry , dna , binding constant , guanine , cytosine , stereochemistry , organic chemistry , binding site , biochemistry , nucleotide , chromatography , gene , essential oil , antimicrobial
Thymol and carvacrol can bind to major and minor grooves of B‐DNA. The aim of this study was to examine the interaction of calf thymus DNA with thymol and carvacrol in aqueous solution and physiological pH with thymol/DNA and carvacrol/DNA (phosphate) molar ratios of 1/20, 1/10, 1/5, and 1/1. Fourier transform infrared and UV‐visible difference spectroscopy were used to determine the thymol and carvacrol binding mode, binding constant, sequence selectivity, DNA secondary structure, and structural variations of thymol/DNA and carvacrol/DNA complexes in aqueous solution. Spectroscopic evidence showed that the thymol and carvacrol interaction occurred mainly through H‐bonding of the thymol and carvacrol OH group to the guanine N7, cytosine N3, and backbone phosphate group with overall binding constant of K (thymol–DNA) = 2.43 × 10 3 M −1 , K (carvacrol–DNA) = 1.55×10 3 M −1 . In thymol and carvacrol–DNA complexes, DNA remains in the B‐family structure. © 2004 Wiley Periodicals, Inc. Biopolymers, 2004