Literature DB >> 18242989

Facile synthesis of substituted trans-2-arylcyclopropylamine inhibitors of the human histone demethylase LSD1 and monoamine oxidases A and B.

David M Gooden1, Dawn M Z Schmidt, Julie A Pollock, Ami M Kabadi, Dewey G McCafferty.   

Abstract

A facile synthetic route to substituted trans-2-arylcyclopropylamines was developed to provide access to mechanism-based inhibitors of the human flavoenzyme oxidase lysine-specific histone demethylase LSD1 and related enzyme family members such as monoamine oxidases A and B.

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Year:  2008        PMID： 18242989      PMCID： PMC2661354          DOI： 10.1016/j.bmcl.2008.01.003

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


  15 in total

Review 1.  Transcription regulation by histone methylation: interplay between different covalent modifications of the core histone tails.

Authors:  Y Zhang; D Reinberg
Journal:  Genes Dev       Date:  2001-09-15       Impact factor: 11.361

2.  trans-2-Aryl-N,N-dipropylcyclopropylamines: synthesis and interactions with 5-HT(1A) receptors.

Authors:  J Vallgårda; U Appelberg; L E Arvidsson; S Hjorth; B E Svensson; U Hacksell
Journal:  J Med Chem       Date:  1996-03-29       Impact factor: 7.446

3.  Histone demethylation by a family of JmjC domain-containing proteins.

Authors:  Yu-ichi Tsukada; Jia Fang; Hediye Erdjument-Bromage; Maria E Warren; Christoph H Borchers; Paul Tempst; Yi Zhang
Journal:  Nature       Date:  2005-12-18       Impact factor: 49.962

4.  Histone demethylation catalysed by LSD1 is a flavin-dependent oxidative process.

Authors:  Federico Forneris; Claudia Binda; Maria Antonietta Vanoni; Andrea Mattevi; Elena Battaglioli
Journal:  FEBS Lett       Date:  2005-04-11       Impact factor: 4.124

5.  N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine receptor agonists.

Authors:  L E Arvidsson; A M Johansson; U Hacksell; J L Nilsson; K Svensson; S Hjorth; T Magnusson; A Carlsson; P Lindberg; B Andersson
Journal:  J Med Chem       Date:  1988-01       Impact factor: 7.446

6.  JHDM2A, a JmjC-containing H3K9 demethylase, facilitates transcription activation by androgen receptor.

Authors:  Kenichi Yamane; Charalambos Toumazou; Yu-ichi Tsukada; Hediye Erdjument-Bromage; Paul Tempst; Jiemin Wong; Yi Zhang
Journal:  Cell       Date:  2006-04-06       Impact factor: 41.582

7.  Fluorinated phenylcyclopropylamines. 2. Effects of aromatic ring substitution and of absolute configuration on inhibition of microbial tyramine oxidase.

Authors:  Thomas C Rosen; Shinichi Yoshida; Roland Fröhlich; Kenneth L Kirk; Günter Haufe
Journal:  J Med Chem       Date:  2004-11-18       Impact factor: 7.446

8.  Histone demethylation mediated by the nuclear amine oxidase homolog LSD1.

Authors:  Yujiang Shi; Fei Lan; Caitlin Matson; Peter Mulligan; Johnathan R Whetstine; Philip A Cole; Robert A Casero; Yang Shi
Journal:  Cell       Date:  2004-12-29       Impact factor: 41.582

9.  Exploring distal regions of the A3 adenosine receptor binding site: sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands.

Authors:  Susanna Tchilibon; Soo-Kyung Kim; Zhan-Guo Gao; Brian A Harris; Joshua B Blaustein; Ariel S Gross; Heng T Duong; Neli Melman; Kenneth A Jacobson
Journal:  Bioorg Med Chem       Date:  2004-05-01       Impact factor: 3.641

10.  Structural basis for the inhibition of the LSD1 histone demethylase by the antidepressant trans-2-phenylcyclopropylamine.

Authors:  Maojun Yang; Jeffrey C Culhane; Lawrence M Szewczuk; Pegah Jalili; Haydn L Ball; Mischa Machius; Philip A Cole; Hongtao Yu
Journal:  Biochemistry       Date:  2007-06-15       Impact factor: 3.162
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  27 in total

Review 1.  Small molecule epigenetic inhibitors targeted to histone lysine methyltransferases and demethylases.

Authors:  Zhanxin Wang; Dinshaw J Patel
Journal:  Q Rev Biophys       Date:  2013-09-02       Impact factor: 5.318

2.  Structure-activity study for (bis)ureidopropyl- and (bis)thioureidopropyldiamine LSD1 inhibitors with 3-5-3 and 3-6-3 carbon backbone architectures.

Authors:  Shannon L Nowotarski; Boobalan Pachaiyappan; Steven L Holshouser; Craig J Kutz; Youxuan Li; Yi Huang; Shiv K Sharma; Robert A Casero; Patrick M Woster
Journal:  Bioorg Med Chem       Date:  2015-02-07       Impact factor: 3.641

3.  Lysine-specific histone demethylase 1 inhibitors control breast cancer proliferation in ERα-dependent and -independent manners.

Authors:  Julie A Pollock; Michelle D Larrea; Jeff S Jasper; Donald P McDonnell; Dewey G McCafferty
Journal:  ACS Chem Biol       Date:  2012-05-10       Impact factor: 5.100

Review 4.  KDM1 class flavin-dependent protein lysine demethylases.

Authors:  Jonathan M Burg; Jennifer E Link; Brittany S Morgan; Frederick J Heller; Amanda E Hargrove; Dewey G McCafferty
Journal:  Biopolymers       Date:  2015-07       Impact factor: 2.505

Review 5.  Inhibitors of Protein Methyltransferases and Demethylases.

Authors:  H Ümit Kaniskan; Michael L Martini; Jian Jin
Journal:  Chem Rev       Date:  2017-03-24       Impact factor: 60.622

6.  Targeting Histone Demethylases: A New Avenue for the Fight against Cancer.

Authors:  Dante Rotili; Antonello Mai
Journal:  Genes Cancer       Date:  2011-06

Review 7.  Computational methods for de novo protein design and its applications to the human immunodeficiency virus 1, purine nucleoside phosphorylase, ubiquitin specific protease 7, and histone demethylases.

Authors:  M L Bellows; C A Floudas
Journal:  Curr Drug Targets       Date:  2010-03       Impact factor: 3.465

8.  New histone demethylase LSD1 inhibitor selectively targets teratocarcinoma and embryonic carcinoma cells.

Authors:  Nam Hoang; Xuan Zhang; Chunxiao Zhang; Van Vo; Feng Leng; Lovely Saxena; Feng Yin; Fei Lu; Guangrong Zheng; Pradip Bhowmik; Hui Zhang
Journal:  Bioorg Med Chem       Date:  2018-02-07       Impact factor: 3.641

9.  Inhibition of LSD1 sensitizes glioblastoma cells to histone deacetylase inhibitors.

Authors:  Melissa M Singh; Christa A Manton; Krishna P Bhat; Wen-Wei Tsai; Kenneth Aldape; Michelle C Barton; Joya Chandra
Journal:  Neuro Oncol       Date:  2011-06-08       Impact factor: 12.300

10.  Use of pH and kinetic isotope effects to establish chemistry as rate-limiting in oxidation of a peptide substrate by LSD1.

Authors:  Helena Gaweska; Michelle Henderson Pozzi; Dawn M Z Schmidt; Dewey G McCafferty; Paul F Fitzpatrick
Journal:  Biochemistry       Date:  2009-06-16       Impact factor: 3.162
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