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

J 2023

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

MARVANOVÁ, Soňa, Kateřina PĚNČÍKOVÁ, Lenka PÁLKOVÁ, Miroslav CIGANEK, Jiří PETRÁŠ et. al.

Basic information

Original name

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

Authors

MARVANOVÁ, Soňa (203 Czech Republic), Kateřina PĚNČÍKOVÁ (203 Czech Republic), Lenka PÁLKOVÁ (203 Czech Republic, belonging to the institution), Miroslav CIGANEK (203 Czech Republic), Jiří PETRÁŠ (203 Czech Republic, belonging to the institution), Anna LNĚNIČKOVÁ (203 Czech Republic, belonging to the institution), Jan VONDRÁČEK (203 Czech Republic) and Miroslav MACHALA (203 Czech Republic, guarantor)

Edition

Science of The Total Environment, Elsevier, 2023, 0048-9697

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10511 Environmental sciences

Country of publisher

Netherlands

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 9.800 in 2022

RIV identification code

RIV/00216224:14310/23:00131710

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.scitotenv.2023.162924

UT WoS

000971841500001

Keywords in English

AhR activity; Airborne particulate matter; Freshwater sediments; Gap junctional intercellular communication; Polycyclic aromatic sulfur heterocyclic compounds

Abstract

V originále

Polycyclic aromatic sulfur heterocyclic compounds (PASHs) belong among ubiquitous environmental pollutants; however, their toxic effects remain poorly understood. Here, we studied the aryl hydrocarbon receptor (AhR)-mediated activity 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 communication 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 significant contributors to the AhR-mediated activity in the environmental samples evaluated in this study. Both induced nuclear 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.

Citovat

MARVANOVÁ, Soňa, Kateřina PĚNČÍKOVÁ, Lenka PÁLKOVÁ, Miroslav CIGANEK, Jiří PETRÁŠ, Anna LNĚNIČKOVÁ, Jan VONDRÁČEK and Miroslav MACHALA. Benzo[b]naphtho[d]thiophenes and naphthylbenzo[b]thiophenes: Their aryl hydrocarbon receptor-mediated activities and environmental presence. Science of The Total Environment. Elsevier, 2023, vol. 879, June 2023, p. 1-12. ISSN 0048-9697. Available from: https://dx.doi.org/10.1016/j.scitotenv.2023.162924.

@article{2311937,
   author = {Marvanová, Soňa and Pěnčíková, Kateřina and Pálková, Lenka and Ciganek, Miroslav and Petráš, Jiří and Lněničková, Anna and Vondráček, Jan and Machala, Miroslav},
   article_number = {June 2023},
   doi = {http://dx.doi.org/10.1016/j.scitotenv.2023.162924},
   keywords = {AhR activity; Airborne particulate matter; Freshwater sediments; Gap junctional intercellular communication; Polycyclic aromatic sulfur heterocyclic compounds},
   language = {eng},
   issn = {0048-9697},
   journal = {Science of The Total Environment},
   title = {Benzo[b]naphtho[d]thiophenes and naphthylbenzo[b]thiophenes: Their aryl hydrocarbon receptor-mediated activities and environmental presence},
   url = {https://doi.org/10.1016/j.scitotenv.2023.162924},
   volume = {879},
   year = {2023}
}

TY  - JOUR
ID  - 2311937
AU  - Marvanová, Soňa - Pěnčíková, Kateřina - Pálková, Lenka - Ciganek, Miroslav - Petráš, Jiří - Lněničková, Anna - Vondráček, Jan - Machala, Miroslav
PY  - 2023
TI  - Benzo[b]naphtho[d]thiophenes and naphthylbenzo[b]thiophenes: Their aryl hydrocarbon receptor-mediated activities and environmental presence
JF  - Science of The Total Environment
VL  - 879
IS  - June 2023
SP  - 1-12
EP  - 1-12
PB  - Elsevier
SN  - 00489697
KW  - AhR activity
KW  - Airborne particulate matter
KW  - Freshwater sediments
KW  - Gap junctional intercellular communication
KW  - Polycyclic aromatic sulfur heterocyclic compounds
UR  - https://doi.org/10.1016/j.scitotenv.2023.162924
N2  - Polycyclic aromatic sulfur heterocyclic compounds (PASHs) belong among ubiquitous environmental pollutants; however, their toxic effects remain poorly understood. Here, we studied the aryl hydrocarbon receptor (AhR)-mediated activity 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 communication 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 significant contributors to the AhR-mediated activity in the environmental samples evaluated in this study. Both induced nuclear 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.
ER  -

MARVANOVÁ, Soňa, Kateřina PĚNČÍKOVÁ, Lenka PÁLKOVÁ, Miroslav CIGANEK, Jiří PETRÁŠ, Anna LNĚNIČKOVÁ, Jan VONDRÁČEK and Miroslav MACHALA. Benzo[b]naphtho[d]thiophenes and naphthylbenzo[b]thiophenes: Their aryl hydrocarbon receptor-mediated activities and environmental presence. \textit{Science of The Total Environment}. Elsevier, 2023, vol.~879, June 2023, p.~1-12. ISSN~0048-9697. Available from: https://dx.doi.org/10.1016/j.scitotenv.2023.162924.

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