9-Methyl-3,4-benzfluorene

Fieser, Louis; Joshel, Lloyd M.

doi:10.1021/ja01861a068

Cited by 7 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…11 H ‐Benzo[ a ]fluoren‐11‐one (B[ a ]FO), B[ b ]FO, 7 H ‐benzo[ c ]fluoren‐7‐one (B[ c ]FO), cyclopenta[ cd ]pyren‐3(4 H )‐one (CPPO), and 6 H ‐benzo[ cd ]pyren‐6‐one (BPO) were synthesized as described previously [26–29]. These compounds were purified by column chromatography and recrystallization.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Aryl hydrocarbon receptor ligand activity of polycyclic aromatic ketones and polycyclic aromatic quinones

Misaki

Kawami

Tanaka

et al. 2007

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

Polycyclic aromatic ketones (PAKs) and polycyclic aromatic quinones (PAQs) are oxygenated polycyclic aromatic hydrocarbons (PAHs), and reports about the aryl hydrocarbon receptor (AhR) ligand activities of these compounds are few. In this study, activation of AhR by 41 polycyclic aromatic compounds (PACs), focusing especially on PAKs and PAQs, was determined by measuring beta-galactosidase activity from a reporter plasmid in yeast engineered to express human AhR and the AhR nuclear translocator proteins and by measuring luciferase activity from mouse hepatoma (H1L1) cells (chemical-activated luciferase expression [CALUX] assay). The PACs used in these experiments included 11 PAKs, seven PAQs, and 21 PAHs. In this study, the PAKs 11H-benzo[a]fluoren-11-one (B[a]FO), 11H-benzo[b]fluoren-11-one (B[b]FO) and 7H-benzo[c]fluoren-7-one and the PAQs 5,12-naphthacenequinone, 1,4-chrysenequinone, and 7,12-benz[a]anthracenequinone showed high AhR activities in H1L1 cells, although these values were not as high as that for benzo[a]pyrene (B[a]P). These PAKs and PAQs showed significantly stronger activities in yeast cells relative to B[a]P. It was predicted that PAKs such as B[a]FO and B[b]FO occupied 0.06% to 1.3% of the total induction equivalents, and each contribution matched the contribution of PAHs such as B[a]P, chrysene, and benz[a]anthracene in gasoline exhaust particulates and airborne particulates using data of CALUX assay.

show abstract

Section: Methodsmentioning

confidence: 99%

“…The chemicals used in the present experiments were 41 PACs, including 11 PAKs, seven PAQs, and 21 PAHs. pyren-6-one (BPO) were synthesized as described previously [26][27][28][29]. These compounds were purified by column chromatography and recrystallization.…”

Section: Introductionmentioning

confidence: 99%

Aryl hydrocarbon receptor ligand activity of polycyclic aromatic ketones and polycyclic aromatic quinones

Misaki

Kawami

Tanaka

et al. 2007

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

show abstract

“…11 H -Benzo[ a ]fluoren-11-one (B[ a ]FO), 11 H -benzo[ b ]fluoren-11-one (B[ b ]FO), 7 H -benzo[ c ]fluoren-7-one (B[ c ]FO), cyclopenta[ cd ]pyren-3(4 H )-one (CPPO), and 6 H -benzo[ cd ]pyren-6-one (BPO) were synthesized as previously described ( − ). These compounds were purified by column chromatography and recrystallization.…”

Section: Methodsmentioning

confidence: 99%

“…These are representative enzymes related to the emergence of DNA adducts and detoxification. were synthesized as previously described (31)(32)(33)(34). These compounds were purified by column chromatography and recrystallization.…”

Section: Introductionmentioning

confidence: 99%

Metabolic Enzyme Induction by HepG2 Cells Exposed to Oxygenated and Nonoxygenated Polycyclic Aromatic Hydrocarbons

Misaki

Matsui

Matsuda

2007

Chem. Res. Toxicol.

View full text Add to dashboard Cite

Oxygenated polycyclic aromatic hydrocarbons (oxy-PAHs) such as polycyclic aromatic quinones and polycyclic aromatic ketones as well as polycyclic aromatic hydrocarbons (PAHs) are abundant in the atmospheric environment. In this study, mRNA induction of six metabolic enzymes including P4501A1, 1A2, and 1B1, aldo-keto reductase 1C1 (AKR1C1), NAD(P)H-dependent quinone oxidoreductase 1 (NQO1), and glutathione S-transferase M1 (GSTM1) were examined in detail in human hepatoma (HepG2) cells exposed to environmentally relevant 13 PAHs and seven oxy-PAHs. Most PAHs such as benzo[a]pyrene (B[a]P) showed significant induction of P4501A1 and 1A2 mRNA, while induction by oxy-PAHs such as 5,12-naphthacenequinone (NCQ) and 11H-benzo[b]fluoren-11-one (B[b]FO) occurred less strongly. AKR1C1 mRNA was significantly induced by oxy-PAHs, 11H-benzo[a]fluoren-11-one (B[a]FO), NCQ, cyclopenta[cd]pyren-3(4H)-one (CPPO), and B[b]FO and also by P450s-inducing PAHs such as B[a]P, benzo[k]fluoranthene (B[k]FA), and dibenz[a,h]anthracene (DB[a,h]A). Both chemical-dependent and time-dependent induction patterns of NQO1 mRNA were of the mixed types of P4501A1 and AKR1C1. The tendency for the decrease of GSTM1 mRNA was observed when exposed to PAHs B[a]P and B[k]FA.

show abstract

“…Benzo [c]fluorene (4 g) (21) was acetylated in the ~~s u a l way (6). :* T h e c r~~d e ketone was ~~n s t a b l e (cf.…”

Section: -Ilcetyl-7-n1ethylbe1t~o[c]fez~oretze ( I B )mentioning

confidence: 99%

5,6-DIMETHYLBENZ[a]ANTHRACENE AND 5,6-DIMETHYLBENZO[c]PHENANTHRENE

Bavin¹

1962

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

9-Methyl-3,4-benzfluorene

Cited by 7 publications

References 0 publications

Aryl hydrocarbon receptor ligand activity of polycyclic aromatic ketones and polycyclic aromatic quinones

Aryl hydrocarbon receptor ligand activity of polycyclic aromatic ketones and polycyclic aromatic quinones

Metabolic Enzyme Induction by HepG2 Cells Exposed to Oxygenated and Nonoxygenated Polycyclic Aromatic Hydrocarbons

5,6-DIMETHYLBENZ[a]ANTHRACENE AND 5,6-DIMETHYLBENZO[c]PHENANTHRENE

Contact Info

Product

Resources

About