Evaluation of estrogenic activities of hydroxylated polycyclic aromatic hydrocarbons in cigarette smoke condensate

Kamiya, Makiko; Toriba, Akira; Onoda, Yu; Kizu, Ryoichi; Hayakawa, Kazuichi

doi:10.1016/j.fct.2005.02.004

Cited by 58 publications

(27 citation statements)

References 34 publications

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“…Table 1 shows results of EC 5 and EC 20 of the AhR agonist compounds. Although EC 5 and EC 20 do not show the same ranking order, the tendency is the same. The most potent compound was 3,4-dihydrobenz[a]anthracen-1(2 H)-one (EC 20 : 0.4 µM).…”

Section: Dr-calux Assaymentioning

confidence: 85%

“…Several PAH hydroxides were shown to have estrogenic/antiestrogenic activity in a reporter gene assay. 20,21) Additionally, air samples reportedly possess toxicity such as mutagenicity, carcinogenicity and reactive oxygen species. 22,23) As a possible contributor to these activities, PAHs and/or PAH derivatives such as ketones and quinines are considered.…”

Section: Discussionmentioning

confidence: 99%

“…For evaluation of agonistic activity, full dose-response curves were not obtainable for the tested compounds. Consequently, luciferase activities of the tested compounds corresponding to EC 5 , EC 20 , and EC 50 (5,20, and 50% Effective Concentrations) of 2,3,7,8-TCDD were used to define EC 5 , EC 20 , and EC 50 concentrations of each compound, as described in a previous report. 14) On the other hand, for measurement of antagonist and potentiation activities, the cells were exposed to 2,3,7,8-TCDD standard (EC 50 : 7.5 pM in well) and experimental samples together.…”

Section: Methodsmentioning

confidence: 99%

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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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Section: Dr-calux Assaymentioning

confidence: 85%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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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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“…liquid chromatography (HPLC) systems with fluorescence detection [7,8], liquid chromatography-mass spectrometry (LC-MS) [9] and gas chromatography-mass spectrometry (GC-MS) [10]. However, there are still some disadvantages, such as time-consuming pretreatment of the sample prior to chromatography analysis [11,12].…”

Section: Introductionmentioning

confidence: 99%

G-quadruplex based impedimetric 2-hydroxyfluorene biosensor using hemin as a peroxidase enzyme mimic

Liang

Liu

2015

Microchim Acta

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We describe a sensitive and selective biosensor for the environmental metabolite 2-hydroxyfluorene (2-HOFlu). It is based on electrochemical impedance spectroscopy and was obtained by assembling a thiolated single-stranded DNA on a gold electrode via S-Au covalent bonding. It is then transformed to a K + -stabilized G-quadruplex-hemin complex which exhibits peroxidase-like activity to catalyze the oxidation of 2-HOFlu by H 2 O 2 . This results in the formation of insoluble products that are precipitated on the gold electrode. As a result, the charge transfer resistance (R CT ) between the solution and the electrode surface is strongly increased within 10 min as demonstrated by using the ferro/ferricyanide system as a redox probe. The difference in the charge transfer resistances (ΔR CT ) before and after incubation of the DNA film with 2-HOFlu and H 2 O 2 serves as the signal for the quantitation of 2-HOFlu with a 1.2. nM detection limit in water of pH 7.4. The assay is highly selective over other selected fluorene derivatives. It was exploited to determine 2-HOFlu in spiked lake water samples where it displayed a detection limit of 3.6 nM. Conceivably, this method has a wide scope in that it may be applied to other analytes for which respective G-quadruplexes are available.

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“…4,6,7) Several other OHPAHs and n-propyl p-hydroxybenzoate were identified as estrogenic compounds in cigarette smoke condensate. 8) We previously evaluated estrogenic/antiestrogenic activities of 14 PAHs and 63 OHPAHs having 2-6 rings by yeast two-hybrid assay and found that PAHs did not show any estrogenic/antiestrogenic activity, but several OHPAHs having 3-5 rings showed activity. Especially, OHPAHs having 4 rings such as 3-, 4-and 10-hydroxybenz[a]anthracenes (3-, 4-and 10-OHBaAs) and 2-hydroxychrysene (2-OHCh) showed strong estrogenic activity.…”

Section: Introductionmentioning

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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Evaluation of estrogenic activities of hydroxylated polycyclic aromatic hydrocarbons in cigarette smoke condensate

Cited by 58 publications

References 34 publications

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

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

G-quadruplex based impedimetric 2-hydroxyfluorene biosensor using hemin as a peroxidase enzyme mimic

Estrogenic/Antiestrogenic Activities of Quinoid Polycyclic Aromatic Hydrocarbons

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