Thymol and carvacrol binding to DNA: model for drug-DNA interaction.
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 x 10(3) M(-1), K(carvacrol-DNA) = 1.55 x 10(3) M(-1). In thymol and carvacrol-DNA complexes, DNA remains in the B-family structure.
Nafisi
Sh
Sh
Department of Chemistry, Azad University, Tehran Central Branch, South Felestine Street, Below the Felestine Square, Tehran 14169 63316, Iran. drshohreh@yahoo.com
Hajiakhoondi
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Yektadoost
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D000818:Animals; D002417:Cattle; D000081007:Cymenes; D004247:DNA / Q000737:chemistry* / Q000187:drug effects / Q000378:metabolism; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism*; D009690:Nucleic Acid Conformation / Q000187:drug effects; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013943:Thymol / Q000737:chemistry / Q000378:metabolism*; D013950:Thymus Gland / Q000737:chemistry
D000081007:Cymenes; D039821:Monoterpenes; D013943:Thymol; D004247:DNA; C073316:carvacrol