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Conventional and unconventional oil and gas extraction, production, and transport lead to increased levels of petroleum\u2010derived polycyclic aromatic hydrocarbons (PAHs) in the environment. PAH exposure has profound effects on reproduction by affecting pathways involved in placental trophoblast cell function and impairing normal placental development and function\u2014key contributors to reproductive success. However, other components found in petroleum and wastewaters from oil and gas extraction, including the sulfur\u2010containing heterocyclic aromatic compounds such as dibenzothiophene (DBT) and its alkylated derivatives, may also impact reproductive success. The goal of this study was to examine the effect of exposure to DBT, a compound commonly detected in the environment, and one of its alkylated analogues, 2,4,7\u2010trimethyldibenzothiophene (2,4,7\u2010DBT), on steroidogenic and angiogenic pathways critical for mammalian development in placental trophoblast cells (HTR\u20108\/SVneo cells). 2,4,7\u2010DBT but not DBT increased estradiol output in association with increased tube\u2010like formation (surrogate for angiogenesis). These changes in angiogenesis did not appear to be related to altered expression of the key placental angiogenic gene targets (<jats:italic>ANGPTL4<\/jats:italic>, <jats:italic>VEGFA<\/jats:italic>, and <jats:italic>PGF<\/jats:italic>). Neither compound showed a concentration related effect on progesterone synthesis or its receptor expression. Our results suggest that 2,4,7\u2010DBT can disrupt key pathways important for placental trophoblast function and highlight the importance of determining the impact of exposure to both parent and alkylated compounds. Further, these data suggest that exposure to sulfur\u2010containing heterocyclic aromatic compounds may lead to placental dysfunction and impact reproductive success at environmentally relevant levels.<\/jats:p>","DOI":"10.1002\/jat.4128","type":"journal-article","created":{"date-parts":[[2020,12,14]],"date-time":"2020-12-14T00:01:06Z","timestamp":1607904066000},"page":"1367-1379","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Effects of dibenzothiophene, a sulfur\u2010containing heterocyclic aromatic hydrocarbon, and its alkylated congener, 2,4,7\u2010trimethyldibenzothiophene, on placental trophoblast cell function"],"prefix":"10.1002","volume":"41","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1627-3957","authenticated-orcid":false,"given":"Sergio","family":"Raez\u2010Villanueva","sequence":"first","affiliation":[{"name":"Department of Obstetrics and Gynecology McMaster University  Hamilton Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Genevieve A.","family":"Perono","sequence":"additional","affiliation":[{"name":"Department of Obstetrics and Gynecology McMaster University  Hamilton Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laiba","family":"Jamshed","sequence":"additional","affiliation":[{"name":"Department of Obstetrics and Gynecology McMaster University  Hamilton Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philippe J.","family":"Thomas","sequence":"additional","affiliation":[{"name":"Environment and Climate Change Canada National Wildlife Research Centre  Ottawa Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4343-5325","authenticated-orcid":false,"given":"Alison C.","family":"Holloway","sequence":"additional","affiliation":[{"name":"Department of Obstetrics and Gynecology McMaster University  Hamilton Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,12,13]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00267-017-0896-2"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1155\/2014\/451906"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fertnstert.2016.07.1099"},{"key":"e_1_2_6_5_1","volume-title":"Hydrocarbons in hair, livers and intestines of sea otters (Enhydra lutris) found dead along the path of the Exxon Valdez oil spill","author":"Ballachey B. 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