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Structure-Dependent in Vitro Metabolism of Alkyl-Substituted Analogues of Triphenyl Phosphate in East Greenland Polar Bears and Ringed Seals
Environmental Science & Technology Letters ( IF 8.9 ) Pub Date : 2018-03-05 00:00:00 , DOI: 10.1021/acs.estlett.8b00064 Adelle Strobel 1, 2 , Robert J. Letcher 1, 2 , William G. Willmore 2 , Christian Sonne 3 , Rune Dietz 3
Environmental Science & Technology Letters ( IF 8.9 ) Pub Date : 2018-03-05 00:00:00 , DOI: 10.1021/acs.estlett.8b00064 Adelle Strobel 1, 2 , Robert J. Letcher 1, 2 , William G. Willmore 2 , Christian Sonne 3 , Rune Dietz 3
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Organophosphate esters (OPEs), used as plasticizers and flame retardants, are major emerging environmental contaminants in the Arctic. OPEs of environmental interest include triphenyl phosphate (TPHP) and a growing array of alkyl-substituted TPHP analogues. Using a microsomal assay of the liver tissue of polar bears and their ringed seal prey, the comparative in vitro metabolism of TPHP was investigated relative to the analogues of isodecyl diphenyl phosphate (IDDPP), (p-tert-butylphenyl) diphenyl phosphate (TBPDPP), tris(p-tert-butylphenyl) phosphate (TTBPP), and two tris(isopropylphenyl) phosphate isomers (T2IPPP and T4IPPP). Polar bear metabolism of the p-tert-butylphenyl-substituted OPEs, TBPDPP and TTBPP, had a substantially slower rate and percent metabolic depletion compared to those with TPHP. Isodecyl- and isopropyl-substituted OPEs, IDDPP, T2IPPP, and T4IPPP, were also more slowly depleted by polar bears than TPHP was. TPHP, IDDPP, T2IPPP, TBPDPP, TTBPP, and T4IPPP were all slowly metabolized by ringed seals. Overall, TPHP in vitro metabolism was clearly affected by o- and p-alkyl substitution that generally hindered the depletion rate. This information is important in understanding the accumulation, biotransformation, and magnification of TPHP and other OPEs in top predator polar bears and their ringed seal prey as well as transfer of OPEs between trophic levels, i.e., ringed seal to polar bears.
中文翻译：
依赖结构的体外代谢的东格陵兰北极熊和环状海豹的磷酸三苯酯的烷基取代类似物。
用作增塑剂和阻燃剂的有机磷酸酯（OPEs）是北极地区主要的新兴环境污染物。环保的OPE包括磷酸三苯酯（TPHP）和越来越多的烷基取代的TPHP类似物。通过对北极熊及其环状海豹猎物的肝组织进行微粒体测定，相对于磷酸异癸基二苯酯（IDDPP），（对叔丁基苯基）磷酸二苯酯（TBPDPP）的类似物，研究了TPHP的体外代谢比较。，磷酸三（对叔丁基苯基）酯（TTBPP）和两种磷酸三（异丙基苯基）酯异构体（T2IPPP和T4IPPP）。在的北极熊代谢对叔丁基与TPHP相比，丁基苯基取代的OPEs TBPDPP和TTBPP的速率和代谢耗竭百分比显着降低。异癸基和异丙基取代的OPE（IDDPP，T2IPPP和T4IPPP）与TPHP相比，被北极熊消耗的速度也更慢。TPHP，IDDPP，T2IPPP，TBPDPP，TTBPP和T4IPPP均被环状密封缓慢代谢。总体而言，TPHP的体外代谢明显受到通常会阻碍耗竭率的邻烷基和对烷基取代的影响。这些信息对于了解顶级捕食者北极熊及其环状海豹捕食者中TPHP和其他OPE的积累，生物转化和放大以及在营养级之间（即环状海豹到北极熊）之间OPE的转移非常重要。
更新日期：2018-03-06
中文翻译：
依赖结构的体外代谢的东格陵兰北极熊和环状海豹的磷酸三苯酯的烷基取代类似物。
用作增塑剂和阻燃剂的有机磷酸酯（OPEs）是北极地区主要的新兴环境污染物。环保的OPE包括磷酸三苯酯（TPHP）和越来越多的烷基取代的TPHP类似物。通过对北极熊及其环状海豹猎物的肝组织进行微粒体测定，相对于磷酸异癸基二苯酯（IDDPP），（对叔丁基苯基）磷酸二苯酯（TBPDPP）的类似物，研究了TPHP的体外代谢比较。，磷酸三（对叔丁基苯基）酯（TTBPP）和两种磷酸三（异丙基苯基）酯异构体（T2IPPP和T4IPPP）。在的北极熊代谢对叔丁基与TPHP相比，丁基苯基取代的OPEs TBPDPP和TTBPP的速率和代谢耗竭百分比显着降低。异癸基和异丙基取代的OPE（IDDPP，T2IPPP和T4IPPP）与TPHP相比，被北极熊消耗的速度也更慢。TPHP，IDDPP，T2IPPP，TBPDPP，TTBPP和T4IPPP均被环状密封缓慢代谢。总体而言，TPHP的体外代谢明显受到通常会阻碍耗竭率的邻烷基和对烷基取代的影响。这些信息对于了解顶级捕食者北极熊及其环状海豹捕食者中TPHP和其他OPE的积累，生物转化和放大以及在营养级之间（即环状海豹到北极熊）之间OPE的转移非常重要。
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