Literature DB >> 31952965

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

Hao Wu1, Binkai Liu1, Ka Yang1, Gabrielle N Winston-McPherson1, Eric D Leisten1, Chad M Vezina2, William A Ricke3, Richard E Peterson1, Weiping Tang4.   

Abstract

The aryl hydrocarbon receptor (AhR) is a ligand activated transcription factor involved in multiple biological processes including immune cell differentiation, intestinal function and inflammation. Based on the scaffold of naturally occurring AhR ligand 6-formylindolo (3,2-b) carbazole (FICZ, 2), a series of analogues has been designed, synthesized and evaluated by cell-based assays. The structure-activity relationships study has successfully led to the discovery of compound 11e with extremely potent activity.
Copyright © 2020 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  AhR; Benign prostatic hyperplasia; Carbazole; FICZ; Transcription factor

Mesh：

Substances：

Year:  2020        PMID： 31952965      PMCID： PMC7007633          DOI： 10.1016/j.bmcl.2020.126959

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


  20 in total

Review 1.  Aryl hydrocarbon receptor (AHR): From selected human target genes and crosstalk with transcription factors to multiple AHR functions.

Authors:  Karl Walter Bock
Journal:  Biochem Pharmacol       Date:  2019-06-19       Impact factor: 5.858

2.  Dioxin receptor is a ligand-dependent E3 ubiquitin ligase.

Authors:  Fumiaki Ohtake; Atsushi Baba; Ichiro Takada; Maiko Okada; Kei Iwasaki; Hiromi Miki; Sayuri Takahashi; Alexander Kouzmenko; Keiko Nohara; Tomoki Chiba; Yoshiaki Fujii-Kuriyama; Shigeaki Kato
Journal:  Nature       Date:  2007-03-29       Impact factor: 49.962

Review 3.  2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity.

Authors:  A Poland; J C Knutson
Journal:  Annu Rev Pharmacol Toxicol       Date:  1982       Impact factor: 13.820

4.  Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands.

Authors:  U Rannug; A Rannug; U Sjöberg; H Li; R Westerholm; J Bergman
Journal:  Chem Biol       Date:  1995-12

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

Authors:  Gabrielle N Winston-McPherson; Dongxu Shu; Weiping Tang
Journal:  Bioorg Med Chem Lett       Date:  2014-06-18       Impact factor: 2.823

Review 6.  Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals.

Authors:  Michael S Denison; Scott R Nagy
Journal:  Annu Rev Pharmacol Toxicol       Date:  2002-01-10       Impact factor: 13.820

7.  Development of Small Molecule Chimeras That Recruit AhR E3 Ligase to Target Proteins.

Authors:  Nobumichi Ohoka; Genichiro Tsuji; Takuji Shoda; Takuma Fujisato; Masaaki Kurihara; Yosuke Demizu; Mikihiko Naito
Journal:  ACS Chem Biol       Date:  2019-10-16       Impact factor: 5.100

8.  FICZ, a tryptophan photoproduct, suppresses pulmonary eosinophilia and Th2-type cytokine production in a mouse model of ovalbumin-induced allergic asthma.

Authors:  Kyu-Tae Jeong; Sung-Jun Hwang; Gap-Soo Oh; Joo-Hung Park
Journal:  Int Immunopharmacol       Date:  2012-05-04       Impact factor: 4.932

Review 9.  The tryptophan derivative 6-formylindolo[3,2-b]carbazole, FICZ, a dynamic mediator of endogenous aryl hydrocarbon receptor signaling, balances cell growth and differentiation.

Authors:  Agneta Rannug; Ulf Rannug
Journal:  Crit Rev Toxicol       Date:  2018-09-18       Impact factor: 5.635

10.  Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor.

Authors:  Cunyu Zhang; Katrina L Creech; William J Zuercher; Timothy M Willson
Journal:  Sci Rep       Date:  2019-07-10       Impact factor: 4.379
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