Environ Sci Pollut Res (2014) 21:14047–14057 DOI 10.1007/s11356-014-3322-9

RESEARCH ARTICLE

Evaluation of HODE-15, FDE-15, CDE-15, and BDE-15 toxicity on adult and embryonic zebrafish (Danio rerio) Li Qin & Fu Liu & Hui Liu & Zhongbo Wei & Ping Sun & Zunyao Wang

Received: 26 March 2014 / Accepted: 9 July 2014 / Published online: 22 July 2014 # Springer-Verlag Berlin Heidelberg 2014

Abstract Diphenyl ether and its derivatives are widely used in the industry of spices, dyes, agrochemicals, and pharmaceuticals. Following the previous study, we selected 4,4′dihydroxydiphenyl ether, 4,4′-difluorodiphenyl ether, 4,4′dichlorodiphenyl ether, and 4,4′-dibromodiphenyl ether as research objects. The LC50 (96 h) values for these compounds in adult zebrafish were determined with the acute test. Also, developmental toxicities of the four substances to zebrafish embryos were observed at 24, 48, 72, and 96 hpf. All the LC50 (96 h) values of these compounds were between 1 and 10 mg/ L, suggesting that they all had moderate toxicity to adult zebrafish. The embryonic test demonstrated that with increasing doses, 4,4′-dihydroxydiphenyl ether decreased the hatching rate, while 4,4′-difluorodiphenyl ether, 4,4′dichlorodiphenyl ether, and 4,4′-dibromodiphenyl ether delayed the hatching time but had little effect on final hatchability at 96 hpf. All of these compounds inhibited larval growth, especially 4,4′-dihydroxydiphenyl ether. Exposure to these chemicals induced embryo yolk sac and pericardial edema. Spine deformation was visible in hatched larvae after 96 hpf 4,4′-dihydroxydiphenyl ether exposure, while tail curvature was observed for the halogenated compounds. The overall results indicated that 4,4′-dihydroxydiphenyl ether, 4,4′difluorodiphenyl ether, 4,4′-dichlorodiphenyl ether, and 4,4′-

Responsible editor: Henner Hollert Li Qin and Fu Liu contributed equally to this work. L. Qin : F. Liu : Z. Wei : P. Sun : Z. Wang (*) State Key Laboratory of Pollution Control and Resources Reuse, School of the Environment, Nanjing University, Jiangsu 210023 Nanjing, China e-mail: [email protected] H. Liu College of Biological and Chemical Engineering, Jiaxing University, Zhejiang 314001 Jiaxing, China

dibromodiphenyl ether all had significant toxicity on adult and embryonic zebrafish. Keywords 4,4′-Dihydroxydiphenyl ether . 4,4′-Difluorodiphenyl ether . 4,4′-Dichlorodiphenyl ether . 4,4′-Dibromodiphenyl ether . Acute toxicity . Developmental toxicity . Zebrafish

Introduction Diphenyl ether and its derivatives with different substituents are widely used in the industry of spices, dyes, agrochemicals, and pharmaceuticals (Nicolaou et al. 1998, 1999; Sawyer 2000). Polybrominated diphenyl ethers (PBDEs) and polychlorinated diphenyl ethers (PCDEs) have become pervasive organic contaminants in the water and soil environment and in the tissues of fish, birds, marine mammals, and humans (Xu et al. 2010; Parolini and Binelli 2012). PBDEs are added to plastic, textiles, carpets, and other materials as flame retardants. With the increasing use of PBDEs, they have been released into the environment eventually and have caused ecological concerns (Buser 1986). PCDEs are mainly from municipal wastewater, rubbish, and incomplete combustion of fly ash (Williams et al. 1991; Nevalainen and Koistinen 1994). The environmental levels of PCDEs are 100–1,000 mg/kg (Kurz and Ballschmiter 1995), which could constitute a potential danger and health risk for the public. Polyhydroxylated diphenyl ethers (PHODEs) are most used in agrochemicals and pharmaceuticals (Huang et al. 2010; Jutemar and Jannasch 2010; Tian et al. 2010; Thomas et al. 2012). Calza et al. (2008) reported that natural seawater could be degraded to form several products, such as 2- and 4-dihydroxydiphenyl ether (HODE), 2,2′-, 4,4′-, and 2,4-HODE, and proved that they were toxic to bacteria and other living organisms. Furthermore, some hydroxylated PBDEs are isolated from

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organism (Fu and Schmitz 1996; Zhang et al. 2008). Levels of these compounds in wildlife and humans continue to rise, raising concerns about potential ecological and health risks associated with exposure to them. Thus, making study on the derivatives of diphenyl ether is necessary. In previous studies, we have carried out the acute toxicity and oxidative stress of mice on diphenyl ether derivatives, 4 , 4 ′ - d i h y d r ox y d i p he n y l e t h e r ( H O D E - 1 5 ) , 4 , 4 ′ difluorodiphenyl ether (FDE-15), 4,4′-dichlorodiphenyl ether (CDE-15), and 4,4′-dibromodiphenyl ether (BDE-15) (Shi et al. 2013; Zhang et al. 2013). For example, Shi et al. (2013) reported that the acute toxicity of fluorinated, chlorinated, and brominated diphenyl ethers in mice was in the order FDE-15

Evaluation of HODE-15, FDE-15, CDE-15, and BDE-15 toxicity on adult and embryonic zebrafish (Danio rerio).

Diphenyl ether and its derivatives are widely used in the industry of spices, dyes, agrochemicals, and pharmaceuticals. Following the previous study, ...
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