Interaction of Hydroxylated Polycyclic Aromatic Hydrocarbons to Estrogen Receptor

Hayakawa, Kazuichi; Onoda, Yu; Tachikawa, Chihiro; Yoshita, Morio; Toriba, Akira; Kameda, Takayuki; Tang, Ning

doi:10.1080/10406630802374556

Cited by 12 publications

(4 citation statements)

References 11 publications

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“…Interestingly, the increased expression of ACE2 and TMPRSS2 by tobacco smoke, which is also a component of PM (Invernizzi et al, 2004), has been implicated in the androgen pathway (Chakladar et al, 2020). Furthermore, PAHs, components in both tobacco smoke and PM, are known to act as endocrine disrupting chemicals (Hayakawa et al, 2008). Therefore, it may be worth investigating the involvement of the androgen pathway in considering the mechanisms by which PM increases the expression of ACE2 and TMPRSS2.…”

Section: Discussionmentioning

confidence: 99%

Exposure to particulate matter upregulates ACE2 and TMPRSS2 expression in the murine lung

Sagawa

Tsujikawa

Honda

et al. 2021

Environmental Research

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Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre -including this research content -immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.

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Section: Discussionmentioning

confidence: 99%

Exposure to particulate matter upregulates ACE2 and TMPRSS2 expression in the murine lung

Sagawa

Tsujikawa

Honda

et al. 2021

Environmental Research

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“…This relationship was observed in the estrogenic and antiestrogenic activities of hydroxylated PAHs with two to six rings through ER binding. 15) The author is now studying on the AhR agonistic and antagonistic activity of PAH quinones and ketones with five rings or more to classify the structure activity relationship.…”

Section: Dr-calux Assaymentioning

confidence: 99%

Evaluation of Toxic Activities of Polycyclic Aromatic Hydrocarbon Derivatives Using In Vitro Bioassays

Bekki

Takigami

Suzuki

et al. 2009

JOURNAL OF HEALTH SCIENCE

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Several polycyclic aromatic hydrocarbons and nitrated polycyclic aromatic hydrocarbons (PAHs/NPAHs) such as benzo [a]pyrene and 1-nitropyrene are mutagens and/or carcinogens. These compounds secondarily generate PAH hydroxides, ketones, and quinones through atmospheric and metabolic reactions. The health effects of these compounds is now an important social concern. For example, lung cancer, bronchitis, whistling and so on. In this work, we evaluated toxicities of 25 PAH derivatives (hydroxides, ketones and quinones) in terms of aryl hydrocarbon receptor (AhR) binding and thyroid hormone-related endpoints using three in vitro bioassays: dioxinresponsive chemical-activated luciferase gene expression (DR-CALUX), thyroid receptor β chemical-activated luciferase gene expression (TRβ-CALUX), and competitive human transthyretin-binding (TTR-binding) assays. Eleven of the 25 PAH derivatives had AhR agonist activity, six had AhR antagonist activity and seven had TRpotentiation activity in the TR-CALUX. Furthermore, PAH quinones and hydroxides had strong TTR-binding activity. 3,4-Dihydrobenz[a]anthracen-1(2 H)-one had the strongest agonist activity (EC 20 : 0.4 µM) as determined by DR-CALUX. PAH ketones showed stronger activity than the control and significant difference by statistical analysis. Benzo[c]phenanthrene-[1,4]-quinone was the most TTR-active compound (IC 50 : 2.5 µM). Both PAH ketones and quinones, which have functional groups with low polarity, had significant activities in all tested assays. These in vitro results suggest that PAH derivatives might have various toxic activities in animals. For estimating the health effects and accessing the environmental risks of PAHs, further studies on the toxicity mechanisms are necessary.

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“…9) Furthermore, RBA is correlated with REP E or REP AE . 14) PAHQs fell into three groups (Fig. 3): RBA ≥ 0.18 and REP AE ≥ 0.42 or REP E = 2.3 such as 1,4-ChQ and BaP-7,8-Q, RBA ≥ 0.11 and REP AE = 0 such as BcPh-1,4-Q and RBA = 0 and REP AE REP E 0 such as 9,10-PhQ.…”

Section: Discussionmentioning

confidence: 99%

Estrogenic/Antiestrogenic Activities of Quinoid Polycyclic Aromatic Hydrocarbons

Hayakawa

Bekki

Yoshita

et al. 2011

JOURNAL OF HEALTH SCIENCE

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Estrogenic and antiestrogenic activities of 19 quinoid polycyclic aromatic hydrocarbons (PAHQs) and 9 ketone PAHs were evaluated by the yeast two-hybrid assay using yeast cells expressing estrogen receptor-α (ERα). Binding affinity of PAHQs to ERα was assayed by the polarized fluorescence method using Fluormone TM ES2. Ten PAHQs having 3-5 rings showed antiestrogenic activities. The most strongly antiestrogenic PAHQs were 1,4-chrysenequinone and 5,6-chrysenequinone. On the other hand, benzo [a]pyrene-3,6-quinone showed the strongest estrogenic activity. However, the other compounds tested did not show so strong estrogenic/antiestrogenic activities. Binding affinity to ER was required but not sufficient for estrogenic/antiestrogenic activities of PAHQs. The length-to-breadth ratios of the rectangular planes surrounding the ring molecules and the distances between the oxygen atom of the carbonyl group and farthest hydrogen atom of estrogenic/antiestrogenic PAHQs were in narrow ranges, suggesting a structure-activity relationship. As interactions between active PAHQ and ER, hydrogen bonding between carbonyl groups and amino acid residues and van der Waals forces were considered.

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Interaction of Hydroxylated Polycyclic Aromatic Hydrocarbons to Estrogen Receptor

Cited by 12 publications

References 11 publications

Exposure to particulate matter upregulates ACE2 and TMPRSS2 expression in the murine lung

Exposure to particulate matter upregulates ACE2 and TMPRSS2 expression in the murine lung

Evaluation of Toxic Activities of Polycyclic Aromatic Hydrocarbon Derivatives Using In Vitro Bioassays

Estrogenic/Antiestrogenic Activities of Quinoid Polycyclic Aromatic Hydrocarbons

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