title: Enantioselectivity tuning of chiral herbicide dichlorprop by copper: roles of reactive oxygen species.
abstract: Reactive oxygen species (ROS) are considered to be the key players in cell toxicity. However, cross talk between the enantioselective toxicity of pesticides, heavy metals, and ROS is poorly understood. To decipher the puzzle, the effects of copper (Cu) on the enantioselective ecotoxicity of the chiral pesticide dichlorprop (DCPP) to Scenedesmus obliquus were investigated. The results showed that the presence of DCPP and Cu, both individually and in combination, caused a sudden increase of ROS. This in turn stimulated the response of antioxidant defenses, impaired subcellular structure and physiological function, and finally resulted in cell growth inhibition. In the absence of Cu, ROS production after exposure to the herbicidally active (R)-enantiomer was higher than that of the (S)-enantiomer, suggesting a preference for an (R)-enantiomer-induced production of ROS. When DCPP and Cu were both added to algae simultaneously, (R)-DCPP preferentially induced production of ROS was observed. However, the enantioselective induced production of ROS was reversed when DCPP was mixed with Cu for 24 h prior to addition to the algae solution. It was also found that the generation of ROS, antioxidant response, and growth inhibition rate in Scenedesmus obliquus were all (R)-enantiomer preferentially induced. These findings implied that ROS play a primary role in chemical contaminant toxicity, and interactions between contaminants can tune the enantioselectivity of chiral herbicides, which should be considered in future risk assessment.
authors.affiliation: Institute of Environmental Sciences, College of Environmental and Resource Sciences, Zhejiang University, Hangzhou 310058, China.
authors.forename: Yuezhong
authors.initials: Y
authors.lastname: Wen
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
authors.forename: Chensi
authors.initials: C
authors.lastname: Shen
authors.forename: Meirong
authors.initials: M
authors.lastname: Zhao
authors.forename: Weiping
authors.initials: W
authors.lastname: Liu
mesh_terms: D015084:2,4-Dichlorophenoxyacetic Acid / Q000031:analogs & derivatives* / Q000633:toxicity; D000975:Antioxidants / Q000378:metabolism; D002463:Cell Membrane Permeability; D002734:Chlorophyll / Q000378:metabolism; D003300:Copper / Q000378:metabolism*; D006540:Herbicides / Q000633:toxicity*; D008315:Malondialdehyde / Q000378:metabolism; D018384:Oxidative Stress / Q000187:drug effects*; D010574:Pesticide Synergists / Q000378:metabolism; D017382:Reactive Oxygen Species / Q000378:metabolism*; D044444:Scenedesmus / Q000254:growth & development / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000975:Antioxidants; D006540:Herbicides; D010574:Pesticide Synergists; D017382:Reactive Oxygen Species; D002734:Chlorophyll; D015084:2,4-Dichlorophenoxyacetic Acid; D008315:Malondialdehyde; D003300:Copper; C010571:dichlorprop