e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Synthesis of 13 C 4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo [a] pyrene

A Wu, D Xu, D Lu, TM Penning, IA Blair, RG Harvey

Index: Wu, Anhui; Xu, Daiwang; Lu, Ding; Penning, Trevor M.; Blair, Ian A.; Harvey, Ronald G. Tetrahedron, 2012 , vol. 68, # 35 p. 7217 - 7233

Full Text: HTML

Citation Number: 14

Abstract

Polycyclic aromatic hydrocarbons (PAHs), such as benzo [a] pyrene (BaP), are ubiquitous environmental contaminants that are implicated in causing lung cancer. BaP is a component of tobacco smoke that is transformed enzymatically to active forms that interact with DNA. We reported previously development of a sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the ...

2-(6-methoxynaphthalen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane Structure

2-(6-methoxynap...

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

N/A Structure

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

N/A Structure

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

2-methoxychrysen-5-ol Structure

2-methoxychryse...

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

N/A Structure

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

2-methoxy-5-ethynylchrysene Structure

2-methoxy-5-eth...

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

2-(2-bromophenyl)-6-methoxynaphthalene Structure

2-(2-bromopheny...

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

ethyl 2-(6-methoxynaphthalen-2-yl)phenylacetate Structure

ethyl 2-(6-meth...

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2-hydroxybenzo(a)pyrene Structure

2-hydroxybenzo(...

5-ethynylchrysene Structure

5-ethynylchrysene

~65%

Benzo(a)pyrene Structure

N/A Structure

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Benzo(a)pyrene Structure

N/A Structure

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Benzo(a)pyrene Structure

(chrysen-5-ylethynyl)trimethylsilane Structure

(chrysen-5-ylet...

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Benzo(a)pyrene Structure

2-(2-naphthalenyl)phenylacetic acid Structure

2-(2-naphthalen...

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Benzo(a)pyrene Structure

2-(2-bromophenyl)naphthalene Structure

2-(2-bromopheny...

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Benzo(a)pyrene Structure

5-Chrysenol Structure

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Benzo(a)pyrene Structure

5,5-Dimethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborinane Structure

5,5-Dimethyl-2-...

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Benzo(a)pyrene Structure

1-methoxy-5-(trimethylsilylethynyl)chrysene Structure

1-methoxy-5-(tr...

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

2-(5-methoxynaphthalen-2-yl)phenylacetic acid Structure

2-(5-methoxynap...

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

1-methoxychrysen-5-ol Structure

1-methoxychryse...

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

N/A Structure

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

N/A Structure

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

ethyl 2-(5-methoxynaphthalen-2-yl)phenylacetate Structure

ethyl 2-(5-meth...

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

1-methoxychrysen-5-ol trifluoromethanesulfonate Structure

1-methoxychryse...

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Benzo[a]pyrene-1,6-dione Structure

Benzo[a]pyrene-...

3-methoxy-5-ethynylchrysene Structure

3-methoxy-5-eth...

~69%

3-Methoxy Benzo[a]pyrene Structure

3-Methoxy Benzo...

N/A Structure

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12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

N/A Structure

~%

12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

ethyl 2-(2-(4-methoxynaphthalen-2-yl)phenyl)acetate Structure

ethyl 2-(2-(4-m...

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12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

2-[2-(4-methoxynaphthalen-2-yl)phenyl]butanoic acid Structure

2-[2-(4-methoxy...

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12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

12-methoxychrysen-5-ol Structure

12-methoxychrys...

~%

12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

N/A Structure

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12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

N/A Structure

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12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

5-ethynyl-12-methoxychrysene Structure

5-ethynyl-12-me...

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12-HYDROXYBENZO[A]PYRENE Structure

12-HYDROXYBENZO...

1-bromo-2,6-dibenzyloxybenzene Structure

1-bromo-2,6-dib...

~%

BENZO(A)PYRENE-7,8-DIOL Structure

BENZO(A)PYRENE-...

1,3-Dibromo-2-iodobenzene Structure

1,3-Dibromo-2-i...

~%

BENZO(A)PYRENE-7,8-DIOL Structure

BENZO(A)PYRENE-...

1-Bromo-2,6-dimethoxybenzene Structure

1-Bromo-2,6-dim...

~%

BENZO(A)PYRENE-7,8-DIOL Structure

BENZO(A)PYRENE-...

2-Bromo-1,3-benzenediol Structure

2-Bromo-1,3-ben...

~%

BENZO(A)PYRENE-7,8-DIOL Structure

BENZO(A)PYRENE-...

(6-Methoxy-2-naphthyl)boronic acid Structure

(6-Methoxy-2-na...

~%

BENZO(A)PYRENE-7,8-DIOL Structure

BENZO(A)PYRENE-...

1-bromo-2,6-dibenzyloxybenzene Structure

1-bromo-2,6-dib...

~%

benzo(a)pyrene-7,8-dione Structure

benzo(a)pyrene-...

1,3-Dibromo-2-iodobenzene Structure

1,3-Dibromo-2-i...

~%

benzo(a)pyrene-7,8-dione Structure

benzo(a)pyrene-...

1-Bromo-2,6-dimethoxybenzene Structure

1-Bromo-2,6-dim...

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benzo(a)pyrene-7,8-dione Structure

benzo(a)pyrene-...

2-Bromo-1,3-benzenediol Structure

2-Bromo-1,3-ben...

~%

benzo(a)pyrene-7,8-dione Structure

benzo(a)pyrene-...

(6-Methoxy-2-naphthyl)boronic acid Structure

(6-Methoxy-2-na...

~%

benzo(a)pyrene-7,8-dione Structure

benzo(a)pyrene-...