Division of Environmental Science and Ecological Engineering, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul02841, Republic of Korea.
Division of Environmental Science and Ecological Engineering, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul02841, Republic of Korea.
J Hazard Mater. 2016 Jul 15;312:200-207. doi: 10.1016/j.jhazmat.2016.03.051. Epub 2016 Mar 19.
Crude oil and refined petroleum products contain many polycyclic and heterocyclic aromatic hydrocarbons, in particular, alkylated PAHs. Although alkylated PAHs are found in significantly higher quantities than their corresponding unsubstituted PAHs, the most studies on the physico-chemical properties and toxicities of these compounds have been conducted on unsubstituted PAHs. In this study, we measured crucial physico-chemical properties (i.e., water solubility, partition coefficients between polydimethylsiloxane and water (KPDMSw), and partition coefficient between liposomes and water (Klipw)) of selected alkylated PAHs, and evaluated their toxicity using the luminescence inhibition of Aliivibrio fischeri and growth inhibition of Raphidocelis subcapitata. In general, the logarithms of these properties for alkylated PAHs showed good linear correlations with log Kow, as did those for unsubstituted PAHs. Changes in molecular symmetry on the introduction of alkyl groups on aromatic ring structure significantly altered water solubility. The inhibition of bacterial luminescence and algal growth by alkylated PAHs can be explained well by the baseline toxicity hypothesis, and good linear relationships between log Kow or log Klipw and log (1/EC50) were found.
原油和精炼石油产品含有许多多环和杂环芳烃，特别是烷基化多环芳烃。虽然烷基化多环芳烃的含量明显高于其相应的未取代多环芳烃，但对这些化合物的物理化学性质和毒性的大多数研究都是在未取代多环芳烃上进行的。在这项研究中，我们测量了选定的烷基化多环芳烃的关键物理化学性质（即水溶性、聚二甲基硅氧烷与水之间的分配系数（KPDMSw）和脂质体与水之间的分配系数（Klipw）），并使用发光抑制发光细菌和抑制水蚤生长来评估它们的毒性。一般来说，烷基化多环芳烃的这些性质的对数与 Kow 的对数呈良好的线性关系，未取代的多环芳烃也是如此。在引入烷基基团到芳香环结构上时，分子对称性的变化显著改变了水溶性。烷基化多环芳烃对细菌发光和藻类生长的抑制作用可以很好地用基线毒性假设来解释，并且发现 Kow 或 Klipw 的对数与 log（1/EC50）之间存在良好的线性关系。
