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Physical Properties of Individual Groundwater Chemicals
Published in John H. Montgomery, Thomas Roy Crompton, Environmental Chemicals Desk Reference, 2017
John H. Montgomery, Thomas Roy Crompton
The gas-phase reaction of N2O5 and naphthalene in an environmental chamber at room temperature resulted in the formation of 1- and 2-nitronaphthalene with approximate yields of 18 and 7.5%, respectively (Pitts et al., 1985). The reaction of naphthalene with NOx to form nitronaphthalene was reported to occur in urban air from St. Louis, Missouri (Ramdahl et al., 1982). The gas-phase reaction of naphthalene with OH ⋅ yielded phthalaldehyde, phthalic anhydride, phthalide, 1,4-naphthoquione, cis- and trans-2-formylcinnamaldehyde, and 2,3-epoxy-1,4-naphthoquinone.
Genotoxicity of quinone: An insight on DNA adducts and its LC-MS-based detection
Published in Critical Reviews in Environmental Science and Technology, 2022
Yue Xiong, Han Yeong Kaw, Lizhong Zhu, Wei Wang
Naphthoquinone is a representative of oxygenated PAHs (oxy-PAHs), in which a range of oxy-PAHs or their oxidative metabolites are structurally similar to naphthoquinone. 1,4-naphthoquinone (1,4-NQ) as a precursor with substantial therapeutic activities in industrial processes has been commonly used (Wellington, 2015). A plethora of evidences indicated that 1,4-NQ did not induce gene mutations in bacteria or mammalian cells, but it showed clastogenic potential in Chinese Hamsters (Fowler et al., 2018). As an isomer of 1,4-NQ, 1,2-naphthoquinone (1,2-NQ) is oxidized from 1,2-dihydroxynaphthalene (1,2-DHN), which is a secondary metabolite of naphthalene (NA) (Saeed et al., 2007). Previous studies have proven that 1,2-NQ, 1,2-DHN and NA can react with DNA. Among which, depurinating N3 adenine (N3Ade) and N7 guanine (N7Gua) adducts were formed through the reaction of 1,2-NQ with calf thymus DNA (ctDNA) by 1,4-Michael addition (Figure 1) (Saeed et al., 2007). Similarly, the same depurinating adducts were generated but with higher yields through the reaction between 1,2-DHN and DNA after activated by the presence of tyrosinase (Saeed et al., 2007). In the lung lobes of B6C3F1 Mouse, Sprague Dawley Rat and Rhesus Macaque Primate, the ability to induce DNA adducts by 1,2-NQ greatly exceeded that of NA (Carratt et al., 2019). Recently, Takuya Matsui et al. discovered a new genotoxicity mechanism for 1,2-NQ where 1,2-NQ can form bulky DNA adducts with deoxyguanosine (dG) (1,2-NQ-epoxide-4-N1-dG, 1,2-NQ-epoxide-3-N2-dG and 1,2-NQ-epoxide-4-N7-dG) by non-enzymatic production of 1,2-NQ-epoxide under specific physiological conditions (Matsui et al., 2019). In which, the generation of 1,2-NQ-epoxide involved rapid reaction between 1,2-NQ and H2O2 that derived from the redox cycle of naphthohydroquinone and another 1,2-NQ derivative named 2-Hydroxy-1,4-NQ (Lamoureux et al., 2008). These works strongly provided a perspective that the genotoxicity of 1,2-NQ is not solely caused by oxidative DNA damage (Ohnishi et al., 2018), and that the DNA adduct can also be formed through Michael addition by 1,2-NQ and 1,2-NQ-expoxide. However, the determination of 1,2-NQ-epoxide and 1,2-NQ-epoxide-DNA adducts in cells with complex intercellular conditions is expected to be extremely challenging. Should intercellular 1,2-NQ-expoxide exist upon exposure of 1,2-NQ to cells, both the oxidation pathway and the types of DNA adducts generated by 1,2-NQ derivatives need to be further explored.