Abstract
Sulforaphane (SFN) is an isothiocyanate found in cruciferous vegetables with anti-inflammatory, anti-oxidant and anti-cancer activities. However, the antioxidant and anticancer mechanism of sulforaphane is not well understood. In the present research, we reported binding modes, binding constants and stability of SFN–DNA and -RNA complexes by Fourier transform infrared (FTIR) and UV–Visible spectroscopic methods. Spectroscopic evidence showed DNA intercalation with some degree of groove binding. SFN binds minor and major grooves of DNA and backbone phosphate (PO2), while RNA binding is through G, U, A bases with some degree of SFN–phosphate (PO2) interaction. Overall binding constants were estimated to be K(SFN–DNA)=3.01 (± 0.035)×104 M-1 and K(SFN–RNA)= 6.63 (±0.042)×103 M-1. At high SFN concentration (SFN/RNA = 1/1), DNA conformation changed from B to A occurred, while RNA remained in A-family structure.
Highlights
Sulforaphane (1-isothiocyanato-4-(methyl-sulfinyl)) butane, a molecule within the isothiocyanate group of organosulfur compounds (Fig 1); is the most characterized isothiocyanate found at high levels in cruciferous vegetables such as broccoli, cabbages, kale, Brussels sprouts, radish, and mustard [1]
SFN acts as an antioxidant by increasing reduced glutathione levels as well as inducing cell cycle arrest and apoptosis [13, 14] by regulation of many molecules including Bcl-2 family proteins, caspases, p21, cyclins and cdks [12, 13]
Major interaction was observed with the bases, mainly with minor groove; A-T rich region and guanine of DNA duplex as evidenced by Fourier transform infrared (FTIR) spectra in Figs 3A and 2A
Summary
Sulforaphane (1-isothiocyanato-4-(methyl-sulfinyl)) butane, a molecule within the isothiocyanate group of organosulfur compounds (Fig 1); is the most characterized isothiocyanate found at high levels in cruciferous vegetables such as broccoli, cabbages, kale, Brussels sprouts, radish, and mustard [1]. It has shown anti-inflammatory, antibiotic, antioxidant and anticarcinogenic properties [2,3,4,5,6,7,8,9,10]. Suppressing effects revealed modulating diverse cellular activities and inhibiting growth of transformed cells [11, 12]. Nrf is PLOS ONE | DOI:10.1371/journal.pone.0127541 June 1, 2015
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