Literature DB >> 15153038

A Highly Abbreviated Synthesis of Dibenzo[def,p]chrysene and Its 12-Methoxy Derivative, a Key Precursor for the Synthesis of the Proximate and Ultimate Carcinogens of Dibenzo[def,p]chrysene.

Arun K Sharma1, Subodh Kumar, Shantu Amin.   

Abstract

Dibenzo[def,p]chrysene (DBC) (1), is by far the most mutagenic and toxic polycyclic aromatic hydrocarbon identified. Its metabolic activation leads to trans-11,12-dihydroxy-11,12-dihydro-DBC (2), which is further metabolized to the ultimate metabolite, anti-trans-11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydro-DBC (3), that binds to DNA causing mutations and ultimately tumor induction. We report a facile route for the syntheses of DBC (1) and its 12-methoxy derivative (12-methoxy-DBC) (13), a key intermediate for the synthesis of 2 and 3, using a Suzuki cross-coupling approach.

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Year:  2004        PMID： 15153038     DOI： 10.1021/jo0303822

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 in total

1.  Preliminary physiologically based pharmacokinetic models for benzo[a]pyrene and dibenzo[def,p]chrysene in rodents.

Authors:  Susan Ritger Crowell; Shantu G Amin; Kim A Anderson; Gowdahalli Krishnegowda; Arun K Sharma; Jolen J Soelberg; David E Williams; Richard A Corley
Journal:  Toxicol Appl Pharmacol       Date:  2011-09-29       Impact factor: 4.219

2.  Mutagenesis and carcinogenesis induced by dibenzo[a,l]pyrene in the mouse oral cavity: a potential new model for oral cancer.

Authors:  Joseph B Guttenplan; Wieslawa Kosinska; Zhong-Lin Zhao; Kun-Ming Chen; Cesar Aliaga; Joseph DelTondo; Timothy Cooper; Yuan-Wan Sun; Shang-Min Zhang; Kun Jiang; Richard Bruggeman; Arun K Sharma; Shantu Amin; Kwangmi Ahn; Karam El-Bayoumy
Journal:  Int J Cancer       Date:  2011-11-19       Impact factor: 7.396

3.  In vitro metabolism of benzo[a]pyrene and dibenzo[def,p]chrysene in rodent and human hepatic microsomes.

Authors:  S R Crowell; S Hanson-Drury; D E Williams; R A Corley
Journal:  Toxicol Lett       Date:  2014-04-21       Impact factor: 4.372

4.  Tissue Distribution, Excretion and Pharmacokinetics of the Environmental Pollutant Dibenzo[def,p]chrysene in Mice.

Authors:  Yuan-Wan Sun; Karam El-Bayoumy; Cesar Aliaga; Alaa S Awad; Krishne Gowda; Shantu Amin; Kun-Ming Chen
Journal:  Chem Res Toxicol       Date:  2015-06-11       Impact factor: 3.739

5.  Identification and quantification of DNA adducts in the oral tissues of mice treated with the environmental carcinogen dibenzo[a,l]pyrene by HPLC-MS/MS.

Authors:  Shang-Min Zhang; Kun-Ming Chen; Cesar Aliaga; Yuan-Wan Sun; Jyh-Ming Lin; Arun K Sharma; Shantu Amin; Karam El-Bayoumy
Journal:  Chem Res Toxicol       Date:  2011-07-19       Impact factor: 3.739

6.  Induction of ovarian cancer and DNA adducts by Dibenzo[a,l]pyrene in the mouse.

Authors:  Kun-Ming Chen; Shang-Min Zhang; Cesar Aliaga; Yuan-Wan Sun; Timothy Cooper; Krishnegowda Gowdahalli; Junjia Zhu; Shantu Amin; Karam El-Bayoumy
Journal:  Chem Res Toxicol       Date:  2012-01-06       Impact factor: 3.739

7.  Impact of pregnancy on the pharmacokinetics of dibenzo[def,p]chrysene in mice.

Authors:  Susan Ritger Crowell; Arun K Sharma; Shantu Amin; Jolen J Soelberg; Natalie C Sadler; Aaron T Wright; William M Baird; David E Williams; Richard A Corley
Journal:  Toxicol Sci       Date:  2013-06-06       Impact factor: 4.849

8.  Characterization of dibenzo[a,l]pyrene-trans-11,12-diol (dibenzo[def,p]chrysene) glucuronidation by UDP-glucuronosyltransferases.

Authors:  Kristine C Olson; Dongxiao Sun; Gang Chen; Arun K Sharma; Shantu Amin; Ira J Ropson; Thomas E Spratt; Philip Lazarus
Journal:  Chem Res Toxicol       Date:  2011-08-05       Impact factor: 3.739

9.  Effects of Black Raspberry Extract and Protocatechuic Acid on Carcinogen-DNA Adducts and Mutagenesis, and Oxidative Stress in Rat and Human Oral Cells.

Authors:  Joseph B Guttenplan; Kun-Ming Chen; Yuan-Wan Sun; Wieslawa Kosinska; Ying Zhou; Seungjin Agatha Kim; Youngjae Sung; Krishne Gowda; Shantu Amin; Gary D Stoner; Karam El-Bayoumy
Journal:  Cancer Prev Res (Phila)       Date:  2016-06-07

10.  Influence of C-5 substituted cytosine and related nucleoside analogs on the formation of benzo[a]pyrene diol epoxide-dG adducts at CG base pairs of DNA.

Authors:  Rebecca Guza; Delshanee Kotandeniya; Kristopher Murphy; Thakshila Dissanayake; Chen Lin; George Madalin Giambasu; Rahul R Lad; Filip Wojciechowski; Shantu Amin; Shana J Sturla; Robert H E Hudson; Darrin M York; Ryszard Jankowiak; Roger Jones; Natalia Y Tretyakova
Journal:  Nucleic Acids Res       Date:  2011-01-17       Impact factor: 16.971
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