Heterocyclic aromatic compounds can be found in crude oil and coal and often co-exist in environmental samples with their homocyclic aromatic counterparts. The target lipid model (TLM) is a modeling framework that relates aquatic toxicity to the octanol–water partition coefficient (K_OW) that has been calibrated and validated for hydrocarbons. A systematic analysis of the applicability of the TLM to heterocyclic aromatic compounds has not been performed. The objective of the present study was to compile reliable toxicity data for heterocycles and determine whether observed toxicity could be successfully described by the TLM. Results indicated that the TLM could be applied to this compound class by adopting an empirically derived coefficient that accounts for partitioning between water and lipid. This coefficient was larger than previously reported for aromatic hydrocarbons, indicating that these heterocyclic compounds exhibit higher affinity to target lipid and toxicity. A mechanistic evaluation confirmed that the hydrogen bonding accepting moieties of the heteroatoms helped explain differences in partitioning behavior. Given the TLM chemical class coefficient reported in the present study, heterocyclic aromatics can now be explicitly incorporated in TLM-based risk assessments of petroleum substances, other products, or environmental media containing these compounds. Environ Toxicol Chem 2021;40:3000–3009. © 2021 The Authors. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC.

中文翻译：

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目标脂质模型在评价杂环芳烃对水生生物毒性中的应用

杂环芳族化合物可以在原油和煤中找到，并且通常与其同环芳族对应物共存于环境样品中。目标脂质模型 (TLM) 是将水生毒性与辛醇-水分配系数 ( K _OW) 已针对碳氢化合物进行校准和验证。尚未对 TLM 对杂环芳族化合物的适用性进行系统分析。本研究的目的是汇编可靠的杂环毒性数据，并确定 TLM 是否可以成功地描述观察到的毒性。结果表明，TLM 可以通过采用一个根据经验得出的系数来解释水和脂质之间的分配，从而应用于该化合物类别。该系数大于先前报道的芳烃，表明这些杂环化合物对目标脂质和毒性表现出更高的亲和力。机械评估证实，杂原子的氢键接受部分有助于解释分配行为的差异。环境毒物化学2021；40:3000–3009。© 2021 作者。Wiley Periodicals LLC 代表 SETAC 出版的Environmental Toxicology and Chemistry 。