DNA interaction with saffron's secondary metabolites safranal, crocetin, and dimethylcrocetin.
Saffron comes from the dried red stigmas of the Crocus sativus L. flower. Except for its use in cooking and in traditional medicine, it has numerous applications as an antitoxic, antioxidant, and anticancer agent due to its secondary metabolites and their derivatives (safranal, crocins, crocetin, dimethylcrocetin). However, there has been no information on the interactions of these secondary metabolites with individual DNA at molecular level. This study was designed to examine the interaction of safranal, crocetin (CRT), and dimethylcrocetin (DMCRT) with calf-thymus DNA in aqueous solution at physiological conditions, using constant DNA concentration (6.25 mM) and various drug/DNA(phosphate) molar ratios from 1/48 to 1/2. FTIR and UV-visible difference spectroscopic methods are used to determine the drug binding sites, the binding constants, and the effects of carotenoids and safranal complexation on the stability and conformation of DNA duplex. Both intercalative and external binding modes were observed, with overall binding constants K(safranal) = 1.24 x 10(3) M(-1), K(CRT) = 6.2 x 10(3) M(-1) and K(DMCRT) = 1.85 x 10(5) M(-1) A partial B- to A-DNA transition occurs at high carotenoids and safranal concentrations.
Kanakis
Charalabos D
CD
Laboratory of Chemistry, Department of Science, Agricultural University of Athens, Athens, Greece.
Tarantilis
Petros A
PA
Tajmir-Riahi
Heidar-Ali
HA
Polissiou
Moschos G
MG
D000818:Animals; D002338:Carotenoids / Q000737:chemistry*; D002417:Cattle; D027622:Crocus / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D035264:Flowers / Q000737:chemistry; D009690:Nucleic Acid Conformation; D028321:Plant Preparations / Q000737:chemistry; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013729:Terpenes / Q000737:chemistry*; D014801:Vitamin A / Q000031:analogs & derivatives; D014867:Water
D053138:Cyclohexenes; D028321:Plant Preparations; D012996:Solutions; D013729:Terpenes; C487773:trans-sodium crocetinate; D014867:Water; D014801:Vitamin A; D002338:Carotenoids; C087963:safranal; D004247:DNA; C427203:calf thymus DNA