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首页> 外文期刊>International Journal of Environmental Research and Public Health >Synthesis and Photoirradiation of Isomeric Ethylchrysenes by UVA Light Leading to Lipid Peroxidation
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Synthesis and Photoirradiation of Isomeric Ethylchrysenes by UVA Light Leading to Lipid Peroxidation

机译：导致脂质过氧化的UVA光的合成和光致同色菊的光辐照

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Polycyclic aromatic hydrocarbons (PAHs) are widespread genotoxic environmental pollutants. We have recently demonstrated that photoirradiation of PAHs leads to cytotoxicity, DNA damage, and induction of lipid peroxidation. In this paper we report the synthesis of all the six isomeric ethylchrysenes and the study of light-induced lipid peroxidation by these ethylchrysenes. 5-Ethylchrysene was synthesized by reaction of 5-keto-5,6,6a,7,8,9,10,10a-octahydrochrysene with CH3CH2MgBr followed by dehydration catalyzed by p-toluenesulfonic acid and dehydrogenation with DDQ in benzene. 1- and 4-Ethylchrysenes were similarly prepared by reaction of 1-keto-1,2,3,4,5,6-hexahydrochrysene and 4-keto-1,2,3,4-tetrahydrochrysenes, respectively with CH3CH2MgBr followed by dehydration and dehydrogenation. Direct acetylation of chrysene followed by Wolff-Kishner or Clemmensen reduction resulted in the formation of 2-, 3-, and 6-ethylchrysenes in 4%, 16%, and 43% yields, respectively. Photoirradiation of these compounds with 7 and 21 J/cm2 UVA light in the presence of methyl linoleate all resulted in lipid peroxidation. For comparison, photoirradiation of 4-methylchrysene and 5-methylchrysene was similarly conducted. For irradiation at a UVA light dose of 21 J/cm2, the level of induced lipid peroxidation is in the order 4-methylchrysene = 5-methylchrysene = 5-ethylchrysene = 4-ethylchrysene = chrysene > 1-ethylchrysene = 2-ethylchrysene > 3-ethylchrysene > 6-ethylchrysene. Compared with chrysene, these results indicate that the ethyl group at C4 or C5 position either slightly enhances or has no effect on the light-induced lipid peroxidation, while at C1-, C2-, C3-, or C6 position reduces light-induced lipid peroxidation.
机译：多环芳烃（PAH）是广泛的遗传毒性环境污染物。最近，我们证明了PAHs的光辐照会导致细胞毒性，DNA损伤和脂质过氧化诱导。在本文中，我们报告了所有六个异构的乙基菊酯的合成以及这些乙基菊酯对光诱导的脂质过氧化作用的研究。 5-乙基丙烯是由5-酮5,6,6a，7,8,9,10,10a-八氢丙烯与CH3CH2MgBr反应，然后通过对甲苯磺酸催化脱水并与DDQ在苯中脱氢而合成的。类似地，通过使1-酮基1,2,3,4,5,6-六氢丙烯和4-酮基1,2,3,4-四氢丙烯醛分别与CH 3 CH 2 MgBr反应，然后脱水，来制备1-和4-乙基丙烯醛。和脱氢。丙烯的直接乙酰化反应，然后进行Wolff-Kishner或Clemmensen还原反应，分别形成4％，16％和43％产率的2-，3-和6-乙基丙烯酰胺。在亚油酸甲酯存在下，用7和21 J / cm2 UVA光对这些化合物进行光辐照都会导致脂质过氧化。为了比较，类似地进行4-甲基丙烯和5-甲基丙烯的光辐照。对于在21 J / cm2的UVA光剂量下进行辐照，诱导的脂质过氧化水平为4-甲基ch = 5-甲基ch = 5-乙基ch = 4-乙基ch = 1-乙基ch = 2-乙基ch> 3 -乙基ch> 6-乙基.。与相比，这些结果表明C4或C5位置的乙基对光诱导的脂质过氧化作用有轻微增强或没有作用，而在C1，C2-，C3-或C6位置的乙基则降低了光诱导的脂质过氧化。

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