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Fructose As a Novel Photosensitizer: Characterization of Reactive Oxygen Species and an Application in Degradation of Diuron and Chlorpyrifos

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Fructose As a Novel Photosensitizer: Characterization of Reactive Oxygen Species and an Application in Degradation of Diuron and Chlorpyrifos Chemosphere 144 (2016) 1690e1697 Contents lists available at ScienceDirect Chemosphere journal homepage: www.elsevier.com/locate/chemosphere Fructose as a novel photosensitizer: Characterization of reactive oxygen species and an application in degradation of diuron and chlorpyrifos * Shaila Nayak a, Juan Muniz b, Christopher M. Sales c, Rohan V. Tikekar d, a Program in Culinary and Food Science, Drexel University, Philadelphia, PA, USA b Department of Nutrition Sciences, Drexel University, Philadelphia, PA, USA c Civil, Architectural and Environmental Engineering, Drexel University, Philadelphia, PA, USA d Department of Nutrition and Food Science, University of Maryland-College Park, MD, USA highlights graphical abstract Fructose underwent photolysis upon exposure to 254 nm UV light. Photolysis products include hydrogen peroxide, singlet oxygen and hy- droxyl radicals. Fructose accelerated UV induced photocatalytic degradation of diuron and chlorpyrifos. Fructose is an attractive photosensi- tizer for decontamination of waste- water. article info abstract Article history: The objective of this study was to identify reactive oxygen species (ROS) generated from the exposure of Received 15 June 2015 fructose solution to the 254 nm ultraviolet (UV) light and evaluate whether fructose can be used as a Received in revised form photosensitizer for accelerated photo-degradation of diuron and chlorpyrifos. We demonstrated that 25 September 2015 hydrogen peroxide, singlet oxygen (1O ) and acidic photolysis products were generated upon UV Accepted 18 October 2015 2 exposure of fructose. Consistent with these findings, UV induced degradation of chlorpyrifos and diuron Available online xxx was accelerated by the presence of 500 mM fructose. The average first order photo-degradation rate À constants in the absence and presence of 500 mM fructose were 0.92 and 2.07 min 1 respectively for Keywords: À1 ɸ Fructose diuron and 0.04 and 0.07 min for chlorpyrifos. The quantum yields ( ) for direct photo-degradation of Advanced oxidative process diuron and chlorpyrifos were 0.003 and 0.001 respectively. In the presence of 500 mM fructose, these Ultraviolet light values increased to 0.006 and 0.002 respectively. Thus, fructose may be an effective photosensitizer. Chlorpyrifos © 2015 Elsevier Ltd. All rights reserved. Diuron Photosensitizer 1. Introduction Fructose has shown significant reactivity upon exposure to 254 nm UV light. A previous study reported that UV (254 nm) exposure of fructose present in fruit juices results in the formation * Corresponding author. Department of Nutrition and Food Science, 112 Skinner of furan (Bule et al., 2010). In previous studies, we demonstrated Building, College Park, MD 20742, USA. that fructose accelerates the degradation rates of patulin and E-mail address: [email protected] (R.V. Tikekar). http://dx.doi.org/10.1016/j.chemosphere.2015.10.074 0045-6535/© 2015 Elsevier Ltd. All rights reserved. S. Nayak et al. / Chemosphere 144 (2016) 1690e1697 1691 ascorbic acid during UV treatment of apple juice (Tikekar et al., (Pittsburgh, PA). Singlet Oxygen Sensor Green (SOSG) was pur- ® 2012, 2011). One study showed that pH of fructose solution chased from Life Technologies (Carlsbad, CA). decreased by 5.29% upon exposure to high intensity pulsed UV light. The lowering of pH was attributed to products formed due to 2.2. UV processing unit photolysis of fructose when exposed to UV light at 254 nm. How- ever, these products were not characterized (Orlowska et al., 2013). The experiments were carried out in a bench top batch UV In another study, by identifying the stable degradation products processing unit (Spectronics Spectrolinker XL-1500 UV Crosslinker, from the photolysis of fructose, it was hypothesized that the open Westbury, NY). The unit consisted of 5 UV lamps (15 W, Spectronics chain form of fructose (0.8% of total fructose in aqueous solution) Corporation, Westbury, NY) generating light at 254 nm. The total undergoes photolysis when irradiated with 254 nm UV light intensity of light incident on samples which were mounted over a resulting in generation of primary species such as hydroxyalkyl, shielded box (46.4 Â 15.9 Â 31.8 cm) was approximately 14.8 mW/ and hydroxyalkyl acyl radicals. These species, upon interaction with cm2. In order to avoid any variations in the intensity of light, the oxygen were hypothesized to form secondary species such as, hy- lamps were allowed to warm up for 5 min before starting the ex- droxyl, peroxyl, superoxide radicals and hydrogen peroxide periments. The temperature during UV treatment was 20e25 C (Triantaphylides et al., 1982). However, formation of only hydrogen and remained constant throughout the experiment. peroxide was experimentally determined and the kinetics of its formation were not elucidated. In congruence with the above 2.3. Generation of reactive oxygen species (ROS) from UV exposed findings, we previously demonstrated that UV exposure of fructose fructose generates miscellaneous reactive oxygen species (ROS), although we did not characterize the chemical nature of these species Fluorescein is commonly used as a probe to detect ROS, due to (Elsinghorst and Tikekar, 2014). Thus, although the reactivity of its sensitivity to oxidation from diverse oxidative species including fructose in 254 nm UV light is known, scarce information is avail- hydroxyl and peroxyl radicals (Ou et al., 2002, 2001). Test solutions able on the formation of reactive oxidative intermediates such as consisted of 1 mM fluorescein prepared in either distilled water or free radicals upon exposure of fructose to UV light. The one study 100 mM phosphate buffer of pH 6.7. Fructose was added to each of that investigated the photolysis of fructose upon exposure to UV these solutions at the concentrations of 10, 100 and 500 mM. light only hypothesized the formation of these reactive in- Treatments were carried out by exposing 10 mL of each solution to termediates by identifying the degradation products. To address UV light for up to 10 min. To ensure the uniformity of treatment this need, the present study gives direct evidence for formation of within each sample, the solutions were stirred throughout the some of these oxidative species and characterizes the kinetics of experiment. A 200 mL of the sample was obtained periodically and their formation using complimentary techniques. We also aimed to the fluorescence from fluorescein was measured using a Gemini evaluate whether the ability of fructose to generate ROS upon XPS fluorescence micro-plate reader (Molecular Devices, Sunny- exposure to UV light can be harnessed to accelerate photo- vale, CA). The excitation and emission wavelengths were set at degradation of recalcitrant organic compounds. To that end, we 485 nm and 510 nm respectively. Fluorescence data was fitted into investigated photo-degradation of an insecticide (chlorpyrifos) and the first order kinetics. an herbicide (diuron) using fructose. To the best of our knowledge, this is the first study that has reported the ability of fructose to act 2.4. Detection of hydrogen peroxide as a photosensitizer to accelerate the photo-degradation of xeno- biotic compounds. The concentration of hydrogen peroxide generated from UV Chlorpyrifos [O,O-diethyl-O-(3,5,6-trichloro-2-pyridinyl)phos- exposure of fructose was measured using the ferrous oxidation- phorothionate], an organophosphate insecticide and diuron [N0- xylenol orange (FOX) method. The principle of this method in- (3,4-dichlorophenyl)-N,N-dimethylurea] a polyurea herbicide, are volves oxidation of ferrous ions by hydrogen peroxide to ferric ions. declared as emerging contaminants by the US-EPA (Richardson, Ferric ions under acidic conditions form a complex with xylenol 2007). Chlorpyrifos inhibits cholinesterase, an enzyme respon- orange which can be measured through spectrophotometry (Bou sible for normal functioning of the nervous system both in insects et al., 2008). The assay solution consisted of 2 mM xylenol or- and humans (Simon et al., 1998). The herbicide, diuron, exhibits its ange, 2.5 mM ferrous sulfate,1 M sorbitol and 250 mM sulfuric acid. activity by inhibiting photosynthesis in weeds (Fuerst and Norman, A100mL of this assay solution was immediately added to the 700 mL 2011) and has been classified as a potential carcinogen by the US- of test sample consisting of UV exposed 500 mM fructose prepared EPA (Cox, 2003). Photosensitizer-induced degradation of these in distilled water or phosphate buffer. This mixture was incubated compounds has been explored before using diverse photosensi- at room temperature for 30 min with continuous gentle shaking. tizers such as hydrogen peroxide, titanium dioxide, zinc oxide and After incubation, absorbance was measured at 560 nm with a zinc sulfide (Devi et al., 2009; Djebbar et al., 2008; Fenoll et al., UVeVis Spectrophotometer (Molecular Devices, Sunnyvale, CA). 2012). However, this is the first study that involves a novel use of 1 fructose as a photosensitizer compound for the degradation of 2.5. Detection and quantification of singlet oxygen ( O2) pesticide residues. 1 Singlet oxygen ( O2) produced during UV treatment of fructose 2. Materials and methods solution was detected using Singlet oxygen sensor green (SOSG). 1 SOSG can react with O2 to produce SOSG endoperoxides (SOSG-EP) 2.1. Chemicals that emit strong green fluorescence at 531 nm (Lin et al., 2013). A 5 mM SOSG stock solution was prepared in methanol. Test solution Diuron (>98% purity), chlorpyrifos (>99.8% purity), fructose, 30% consisted of 500 mM fructose sample, prepared in phosphate buffer v/v hydrogen peroxide, xylenol orange, ferrous sulfate, sorbitol, of pH 6.7 and mixed with 5 mM SOSG added from stock solution sulfuric acid, ascorbic acid, fluorescein, sodium phosphate mono- immediately before use. This solution was exposed to UV light at basic monohydrate, sodium phosphate dibasic 7-hydrate, titanium 254 nm. Fluorescence was measured at an interval of 1 min of UV dioxide, pesticide grade acetonitrile and iso-octane were purchased exposure with excitation and emission wavelengths of 504 and ® from Sigma Aldrich (Sigma, St. Louis, MO) and Fisher Scientific 525 nm respectively.
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