【作者】 汪丽；

【导师】 陈景文；

【作者基本信息】 大连理工大学 ， 环境科学， 2006， 硕士

【摘要】 蒽醌类化合物是重要的化工原料,而且研究表明部分蒽醌类化合物具有光敏活性,因此,排放到水环境中的此类物质吸收可见光后可能发生光化学反应,对水生生态系统造成严重的威胁。大型溞是国际公认的标准实验生物,广泛应用于污染物的生态毒性评价。 本文研究了两种光照（光暗比=14:10h和0:24h）条件下,20种蒽醌类化合物对大型溞的急性毒性,比较了两种助溶剂（二甲基亚砜和丙酮）对此类化合物的毒性影响,根据毒性数据建立了定量结构-活性关系（QSAR）模型,初步讨论了光致毒性的机理。结果表明,在两种光照条件下和最大溶解度时,7种蒽醌类化合物均未表现出毒性;1,2-二羟基蒽醌和1,4-二羟基蒽醌在可见光条件下转化为其它物质导致毒性变化;剩余11种化合物在可见光下通过光敏化作用导致毒性增加;两种助溶剂不影响蒽醌类化合物对大型溞的光致毒性。蒽醌类化合物因其取代基种类不同（-NH₂、-OH、-Cl、-Br、-NO₂）、取代基位置不同和取代基数目不同,而表现出对大型溞光致毒性的不同。化合物最低未占据分子轨道能和最高占据分子轨道能之间的能级差,可用于初步判断蒽醌类化合物对大型溞的潜在光致毒性。11种蒽醌类化合物对大型溞光敏化毒性的最佳OSAR模型的Q_cum²为0.902,具有较好的稳健性和预测能力。影响蒽醌类化合物对大型溞光敏化毒性的主要因素是分子的极性、电子的跃迁能力和原子最负净电荷。更多还原

【Abstract】 Anthraquinones are an important industrial material, and it is reported that some anthraquinones have photosensitization activity. Thus there compounds, discharged into aqueous system, may take place photochemistry reaction after absorb visible light, and lead to have a great risk for aqueous ecology systems. Daphnia magna have been used word-wide as a standard test organism for ecotoxicological evaluation of contamination.The thesis study the acute toxicity of 20 anthraquinones to Daphnia magna under two different light/dark cycles, 14 （light）: 10 h （dark）, and sole dark. Furthermore, their photoinduced toxicity to Daphnia magna and the effects of two solubilizing agents on the photoinduced toxicity was investigated. Based on toxicity data, a quantitative structure-activity relationship （QSAR） was obtained. The mechanism of the photoinduced toxicity was also discussed. The results indicated that seven compounds were not toxic. 1,2-Dihydroxyanthraquinone and 1,4-dihydroxyanthraquinone were subject to photomodification under the daylight fluorescent lamp. The photoinduced toxicity of the tested eleven anthraquinones to Daphnia magna was enhanced due to photosensitization. The two co-solvents, dimethylsulfoxide and acetone, did not affect the photoinduced toxicity of the compounds. The photoinduced toxicity of the anthraquinones depended on the number, position and electron-donating ability of the substituent groups to the parent structure of anthraquinone. The gap between the energy of the highest occupied molecular orbital and the lowest unoccupied molecular orbital can be used as an indicator of the potential photoinduced toxicity of anthraquinones to Daphnia magna. Q_cum² of the final models of the toxicity of the tested eleven anthraquinones to Daphnia magna, were higher than 0.902, indicating that the models have good predictive ability and robustness. The main factors governing photoinduced toxicity of the anthraquinone are molecular polarity, the ability of electron transition and the largest negative net atomic charges.更多还原