Benzo[b]naphtho[d]thiophenes and naphthylbenzo[b]thiophenes: Their aryl hydrocarbon receptor-mediated activities and environmental presence

0571976 - BFÚ 2024 RIV NL eng J - Článek v odborném periodiku
Marvanová, S. - Pěnčíková, K. - Palková, L. - Ciganek, M. - Petráš, Jiří - Lněničková, Anna - Vondráček, Jan - Machala, M.
Benzo[b]naphtho[d]thiophenes and naphthylbenzo[b]thiophenes: Their aryl hydrocarbon receptor-mediated activities and environmental presence.
Science of the Total Environment. Roč. 879, JUN 25 2023 (2023), č. článku 162924. ISSN 0048-9697. E-ISSN 1879-1026
Grant CEP: GA ČR(CZ) GA21-00533S
Institucionální podpora: RVO:68081707
Klíčová slova: Polycyclic aromatic sulfur heterocyclic * compounds * AhR activity * Gap junctional intercellular communication * Airborne particulate matter * Freshwater sediments
Obor OECD: Ecology
Impakt faktor: 9.8, rok: 2022
Způsob publikování: Omezený přístup
https://www.sciencedirect.com/science/article/pii/S0048969723015401?via%3Dihub

Polycyclic aromatic sulfur heterocyclic compounds (PASHs) belong among ubiquitous environmental pollutants, how-ever, their toxic effects remain poorly understood. Here, we studied the aryl hydrocarbon receptor (AhR)-mediated ac-tivity of dibenzothiophene, benzo[b]naphtho[d]thiophenes, and naphthylbenzo[b]thiophenes, as well as their presence in two types of environmental matrices: river sediments collected from both rural and urban areas, and in airborne particulate matter (PM2.5) sampled in cities with different levels and sources of pollution. Benzo[b]naphtho [2,1-d]thiophene, benzo[b]naphtho[2,3-d]thiophene, 2,2-naphthylbenzo[b]thiophene, and 2,1-naphthylbenzo[b] thiophene were newly identified as efficient AhR agonists in both rat and human AhR-based reporter gene assays, with 2,2-naphthylbenzo[b]thiophene being the most potent compound identified in both species. Benzo[b]naphtho [1,2-d]thiophene and 3,2-naphthylbenzo[b]thiophene elicited AhR-mediated activity only in the rat liver cell model, while dibenzothiophene and 3,1-naphthylbenzo[b]thiophene were inactive in either cell type. Independently of their ability to activate the AhR, benzo[b]naphtho[1,2-d]thiophene, 2,1-naphthylbenzo[b]thiophene, 3,1-naphthylbenzo[b]thiophene, and 3,2-naphthylbenzo[b]thiophene inhibited gap junctional intercellular communica-tion in a model of rat liver epithelial cells. Benzo[b]naphtho[d]thiophenes were dominant PASHs present in both PM2.5 and sediment samples, with benzo[b]naphtho[2,1-d]thiophene being the most abundant one, followed by benzo[b]naphtho[2,3-d]thiophene. The levels of naphthylbenzo[b]thiophenes were mostly low or below detection limit. Benzo[b]naphtho[2,1-d]thiophene and benzo[b]naphtho[2,3-d]thiophene were identified as the most signifi-cant contributors to the AhR-mediated activity in the environmental samples evaluated in this study. Both induced nu-clear translocation of the AhR, and they induced CYP1A1 expression in a time-dependent manner, suggesting that their AhR-mediated activity may depend on the rate of their intracellular metabolism. In conclusion, some PASHs could be significant contributors to the overall AhR-mediated toxicity of complex environmental samples suggesting that more attention should be paid to the potential health impacts of this group of environmental pollutants.
Trvalý link: https://hdl.handle.net/11104/0349923