Formation of estrogenic metabolites of benzo[a]pyrene and chrysene by cytochrome P450 activity and their combined and supra-maximal estrogenic activity

Lipzig, Marola M.H. van; Vermeulen, Nico; Gusinu, Renato; Legler, Juliette; Frank, Heinz; Seidel, Albrecht; Meerman, John H.N.

doi:10.1016/j.etap.2004.03.010

Cited by 82 publications

(58 citation statements)

References 54 publications

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“…1). Several hydroxy-PAHs such as hydroxylated derivatives of benzo[a]pyrene and chrysene have been shown to possess estrogenic activity, as indicated by in vitro test systems based on genetically modified yeast or mammalian cell lines (Charles et al, 2000;Fertuck et al, 2001;Kamiya et al, 2005;van Lipzig et al, 2005;Hayakawa et al, 2007). Therefore, we hypothesized that hydroxy-PAHs contribute in some extent to estrogenic activity previously observed with ambient particulate matter (Clemons et al, 1998;Wang et al, 2004;Klein et al, 2006).…”

Section: Introductionmentioning

confidence: 92%

“…Furthermore, hydroxylated PAHs can be formed in organisms, after the intake of parental PAHs, through biotransformation catalyzed by cytochrome P450 (CYP) enzymes (Charles et al, 2000;Fertuck et al, 2001;van Lipzig et al, 2005). In vitro estrogenicity observed with certain PAHs is supposed to be predominantly due to their hydroxylated metabolites formed in the exposed cells (Charles et al, 2000;Fertuck et al, 2001;van Lipzig et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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In vitro estrogenicity of ambient particulate matter: contribution of hydroxylated polycyclic aromatic hydrocarbons

Wenger

Gerecke

Heeb

et al. 2008

J of Applied Toxicology

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Atmospheric particulate matter (PM1) was collected at an urban and a rural site in Switzerland during a hibernal high air pollution episode and was investigated for estrogenicity using an estrogen-sensitive reporter gene assay (ER-CALUX). All samples that were tested induced estrogen receptor-mediated gene expression in T47D human breast adenocarcinoma cells. Observed estrogenic activities corresponded to 17beta-estradiol (E2) CALUX equivalent concentrations ranging from 2 to 23 ng E2-CEQ per gram of PM1 (particulate matter of < or = 1 microm aerodynamic diameter) and from 0.07 to 1.25 pg E2-CEQ per m(3) of sampled air. There was a strong correlation between the PM1 estrogenicity of the urban and rural sites (r = 0.92). Five hydroxylated polycyclic aromatic hydrocarbons (hydroxy-PAHs), which show structural similarities to E2, were assessed for their estrogenic activity. The following order of estrogenic potency was found: 2-hydroxychrysene > 2-hydroxyphenanthrene > 1-hydroxypyrene > 2-hydroxynaphthalene > 1-hydroxynaphthalene. Three of these hydroxy-PAHs, namely 2-hydroxyphenanthrene, 2-hydroxynaphthalene and 1-hydroxynaphthalene, were detected in all PM1 extracts. However, they contributed only 0.01-0.2% to the overall estrogenic activity. Hence, mainly other estrogenic compounds not yet identified by chemical analysis must be responsible for the observed activity. The temporal trend of PM1 estrogenicity at the urban and rural site, respectively, was compared with the time course of several air pollutants (NO2, NO, SO2, O3, CO) and meteorological parameters (temperature, humidity, air pressure, solar irradiation, wind velocity). However, specific emission sources and formation processes of atmospheric xenoestrogens could not be elucidated. This study showed that ambient particulate matter contains compounds that are able to interact with estrogen receptors in vitro and potentially also interfere with estrogen-regulated pathways in vivo.

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Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

In vitro estrogenicity of ambient particulate matter: contribution of hydroxylated polycyclic aromatic hydrocarbons

Wenger

Gerecke

Heeb

et al. 2008

J of Applied Toxicology

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“…Earlier, BP had been found to exhibit estrogenic activity in various in vitro and in vivo systems following metabolism [38,39]. For several mono-hydroxylated BPs (i.e.…”

Section: Pah Binding To the Estrogen Receptormentioning

confidence: 99%

Fluorescence line-narrowing spectroscopy for probing purposes in bioanalytical and environmental chemistry

Ariese¹,

Bader²,

Gooijer³

2008

TrAC Trends in Analytical Chemistry

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Fluorescence line-narrowing spectroscopy (FLNS) is a cryogenic technique that can be used to obtain high-resolution fluorescence spectra. The technique has mainly been used for fingerprint identification. However, this review focuses on the trend to use FLNS for probing purposes: obtaining information on interactions with the local environment or determining conformations.We briefly discuss the basics of FLNS, solute-matrix interactions and important instrumental aspects. We describe examples from various bioanalytical fields: DNA adducts of the aromatic carcinogen benzo[a]pyrene (BP); binding of BP metabolites to monoclonal antibodies or the estrogen receptor; FLNS studies of porphyrin-containing proteins; and, photosynthetic systems.As an illustration from the field of environmental chemistry, we discuss the use of luminescence line-narrowing spectroscopy -a special mode of FLNS -to study the complexation of lanthanides to humic substances. ª

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“…Além disso, os HPAs-hidroxilados podem ser formados no organismo após a ingestão de HPA parenteralmente, por biotransformação catalisada pelo citocromo P450 (CYP) (Charles et al, 2000;Fertuck et al, 2001;van Lipzig et al, 2005). A estrogenicidade in vitro pode ser observada em certos HPAs, e ocorre supostamente devido a metabólitos hidroxilados formados em células expostas (Charles et al, 2000;Fertuck et al, 2001;Lipzig van et al, 2005 (Kuiper et al, 1998).…”

Section: Discussionunclassified

“…Além de processos atmosféricos, hidroxi-HPAs e seus precursores são emitidos diretamente a partir de processos de combustão e são encontrados, por exemplo, em escape de motores a diesel (Sidhu et al, 2005;Heeb et al, 2008). Além disso, HPAs hidroxilados podem ser formados nos organismos após a ingestão de HPAs parenterais, através de biotransformação catalisada pelo citocromo P450 (CYP) (Charles et al, 2000;Fertuck et al, 2001;van Lipzig et al, 2005). In vitro, a estrogenicidade observada com determinados HPAs é suspeita de ser predominantemente formada por seus metabolitos hidroxilados nas células expostas (Charles et al, 2000;Fertuck et al, 2001;van Lipzig et al, 2005).…”

Section: Introductionunclassified

Efeitos da participação de esteroides-like provenientes da poluição atmosférica no epitélio das vias aéreas em camundongos machos e fêmeas

Yoshizaki¹

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Formation of estrogenic metabolites of benzo[a]pyrene and chrysene by cytochrome P450 activity and their combined and supra-maximal estrogenic activity

Cited by 82 publications

References 54 publications

In vitro estrogenicity of ambient particulate matter: contribution of hydroxylated polycyclic aromatic hydrocarbons

In vitro estrogenicity of ambient particulate matter: contribution of hydroxylated polycyclic aromatic hydrocarbons

Fluorescence line-narrowing spectroscopy for probing purposes in bioanalytical and environmental chemistry

Efeitos da participação de esteroides-like provenientes da poluição atmosférica no epitélio das vias aéreas em camundongos machos e fêmeas

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