Literature DB >> 24997686

Synthesis and biological evaluation of 2,3'-diindolylmethanes as agonists of aryl hydrocarbon receptor.

Gabrielle N Winston-McPherson1, Dongxu Shu2, Weiping Tang3.   

Abstract

Recent studies suggest that arylhydrocarbon receptor (AhR) may be a target for a number of diseases. Natural product malassezin is a AhR agonist with an interesting 2,3'-diindolylmethane skeleton. We have prepared a series of analogues of natural product malassezin using our recently developed method and tested the activity of these analogues against AhR in a cell-based assay. We found that a methyl substituent at 1'-N can significantly increase the activity and the 2-formyl group is not critical for some diindolylmethanes.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Agonist; AhR; Diindolylmethane; Indole; Transcription factor

Mesh:

Substances:

Year:  2014        PMID: 24997686      PMCID: PMC4130779          DOI: 10.1016/j.bmcl.2014.06.009

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  30 in total

Review 1.  Ethoxyresorufin-O-deethylase (EROD) activity in fish as a biomarker of chemical exposure.

Authors:  J J Whyte; R E Jung; C J Schmitt; D E Tillitt
Journal:  Crit Rev Toxicol       Date:  2000-07       Impact factor: 5.635

2.  Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur.

Authors:  G Wille; P Mayser; W Thoma; T Monsees; A Baumgart; H J Schmitz; D Schrenk; K Polborn; W Steglich
Journal:  Bioorg Med Chem       Date:  2001-04       Impact factor: 3.641

3.  Malassezin, a novel agonist of the aryl hydrocarbon receptor from the yeast Malassezia furfur, induces apoptosis in primary human melanocytes.

Authors:  Hans-Joachim Krämer; Monika Podobinska; Andrea Bartsch; Achim Battmann; Wiebke Thoma; August Bernd; Wolfgang Kummer; Bernhard Irlinger; Wolfgang Steglich; Peter Mayser
Journal:  Chembiochem       Date:  2005-05       Impact factor: 3.164

4.  Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b]carbazoles.

Authors:  Dongxu Shu; Gabrielle N Winston-McPherson; Wangze Song; Weiping Tang
Journal:  Org Lett       Date:  2013-08-05       Impact factor: 6.005

5.  Constitutive activation of the aromatic hydrocarbon receptor.

Authors:  C Y Chang; A Puga
Journal:  Mol Cell Biol       Date:  1998-01       Impact factor: 4.272

Review 6.  Ah receptor signaling pathways.

Authors:  J V Schmidt; C A Bradfield
Journal:  Annu Rev Cell Dev Biol       Date:  1996       Impact factor: 13.827

7.  The suggested physiologic aryl hydrocarbon receptor activator and cytochrome P4501 substrate 6-formylindolo[3,2-b]carbazole is present in humans.

Authors:  Emma Wincent; Nahid Amini; Sandra Luecke; Hansruedi Glatt; Jan Bergman; Carlo Crescenzi; Agneta Rannug; Ulf Rannug
Journal:  J Biol Chem       Date:  2008-12-02       Impact factor: 5.157

8.  Response of murine epidermis to 2,3,7,8-tetrachlorodibenzo-p-dioxin: interaction of the ah and hr loci.

Authors:  J C Knutson; A Poland
Journal:  Cell       Date:  1982-08       Impact factor: 41.582

Review 9.  The search for endogenous activators of the aryl hydrocarbon receptor.

Authors:  Linh P Nguyen; Christopher A Bradfield
Journal:  Chem Res Toxicol       Date:  2007-12-13       Impact factor: 3.739

10.  Control of T(reg) and T(H)17 cell differentiation by the aryl hydrocarbon receptor.

Authors:  Francisco J Quintana; Alexandre S Basso; Antonio H Iglesias; Thomas Korn; Mauricio F Farez; Estelle Bettelli; Mario Caccamo; Mohamed Oukka; Howard L Weiner
Journal:  Nature       Date:  2008-03-23       Impact factor: 49.962

View more
  4 in total

1.  Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene-Copper Complex.

Authors:  Yuan Huang; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

2.  Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

Authors:  Hui Li; Xiaoxun Li; Hao-Yuan Wang; Gabrielle N Winston-McPherson; Hao-miao Julie Geng; Ilia A Guzei; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2014-10-21       Impact factor: 6.222

3.  Synthesis and biological evaluation of FICZ analogues as agonists of aryl hydrocarbon receptor.

Authors:  Hao Wu; Binkai Liu; Ka Yang; Gabrielle N Winston-McPherson; Eric D Leisten; Chad M Vezina; William A Ricke; Richard E Peterson; Weiping Tang
Journal:  Bioorg Med Chem Lett       Date:  2020-01-07       Impact factor: 2.823

4.  Synthesis of a Novel Type of 2,3'-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles.

Authors:  Lisa Cooper; José Miguel Alonso; Louise Eagling; Helen Newson; Sachini Herath; Christopher Thomson; Andrew Lister; Catherine Howsham; Brian Cox; María Paz Muñoz
Journal:  Chemistry       Date:  2018-03-05       Impact factor: 5.236

  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.