Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Synthesis of 13C2-Benzo[a]pyrene and its 7,8-Dihydrodiol and 7,8-Dione Implicated as Carcinogenic Metabolites.

Literature DB >> 24155502

Synthesis of ¹³C₂-Benzo[a]pyrene and its 7,8-Dihydrodiol and 7,8-Dione Implicated as Carcinogenic Metabolites.

Chongzhao Ran¹, Daiwang Xu, Qing Dai, Trevor M Penning, Ian A Blair, Ronald G Harvey.

Abstract

Synthesis of the 13C2-labelled analogues of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene and its active metabolites are described. The method entails Pd-catalyzed Suzuki-Miyaura coupling of a naphthalene boronic acid with 2-bromobenzene-1,3-dialdehyde followed by Wittig reaction of the product with 13CH2=PPh3.

Entities: Chemical Disease Gene

Year: 2008 PMID： 24155502 PMCID： PMC3804341 DOI： 10.1016/j.tetlet.2008.05.033

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

19 in total

1. Carcinogenicity of polycyclic aromatic hydrocarbons.

Authors: Kurt Straif; Robert Baan; Yann Grosse; Béatrice Secretan; Fatiha El Ghissassi; Vincent Cogliano
Journal: Lancet Oncol Date: 2005-12 Impact factor: 41.316

Review 2. Synergistic mechanisms in carcinogenesis by polycyclic aromatic hydrocarbons and by tobacco smoke: a bio-historical perspective with updates.

Authors: H Rubin
Journal: Carcinogenesis Date: 2001-12 Impact factor: 4.944

Review 3. Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action.

Authors: William M Baird; Louisa A Hooven; Brinda Mahadevan
Journal: Environ Mol Mutagen Date: 2005 Mar-Apr Impact factor: 3.216

4. The ubiquitous aldehyde reductase (AKR1A1) oxidizes proximate carcinogen trans-dihydrodiols to o-quinones: potential role in polycyclic aromatic hydrocarbon activation.

Authors: N T Palackal; M E Burczynski; R G Harvey; T M Penning
Journal: Biochemistry Date: 2001-09-11 Impact factor: 3.162

5. Aldo-keto reductase- and cytochrome P450-dependent formation of benzo[a]pyrene-derived DNA adducts in human bronchoalveolar cells.

Authors: Qian Ruan; Stacy L Gelhaus; Trevor M Penning; Ronald G Harvey; Ian A Blair
Journal: Chem Res Toxicol Date: 2007-02-13 Impact factor: 3.739

6. Synthesis of dibenzo[def,p]chrysene, its active metabolites, and their 13C-labeled analogues.

Authors: Daiwang Xu; Yazhen Duan; Ian A Blair; Trevor M Penning; Ronald G Harvey
Journal: Org Lett Date: 2008-02-20 Impact factor: 6.005

7. Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis.

Authors: Ronald G Harvey; Qing Dai; Chongzhao Ran; Trevor M Penning
Journal: J Org Chem Date: 2004-03-19 Impact factor: 4.354

8. Metabolism of benzo[a]pyrene in human bronchoalveolar H358 cells using liquid chromatography-mass spectrometry.

Authors: Hao Jiang; Stacy L Gelhaus; Dipti Mangal; Ronald G Harvey; Ian A Blair; Trevor M Penning
Journal: Chem Res Toxicol Date: 2007-08-17 Impact factor: 3.739

9. A convenient new synthesis of benzo[a]pyrene.

Authors: Ronald G Harvey; Keunpoong Lim; Qing Dai
Journal: J Org Chem Date: 2004-02-20 Impact factor: 4.354

10. Quantification of benzo[a]pyrene diol epoxide DNA-adducts by stable isotope dilution liquid chromatography/tandem mass spectrometry.

Authors: Qian Ruan; Hye-Young H Kim; Hao Jiang; Trevor M Penning; Ronald G Harvey; Ian A Blair
Journal: Rapid Commun Mass Spectrom Date: 2006 Impact factor: 2.419

6 in total

1. Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents.

Authors: Anhui Wu; Yazhen Duan; Daiwang Xu; Trevor M Penning; Ronald G Harvey
Journal: Tetrahedron Date: 2010-03-20 Impact factor: 2.457

2. Preparation of phenalenes and hydronaphthacenes through tandem alkyne Fischer-carbene complex coupling and inter- or intramolecular Diels-Alder reactions.

Authors: Rajesh Kumar Patti; Shaofeng Duan; Zhipeng Wang; James W Herndon
Journal: Tetrahedron Lett Date: 2011-08-10 Impact factor: 2.415

3. Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer.

Authors: Daiwang Xu; Trevor M Penning; Ian A Blair; Ronald G Harvey
Journal: J Org Chem Date: 2009-01-16 Impact factor: 4.354