Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase.


Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
15 Jan 2019
Historique:
received: 02 08 2018
revised: 06 10 2018
accepted: 05 11 2018
pubmed: 24 11 2018
medline: 8 2 2019
entrez: 24 11 2018
Statut: ppublish

Résumé

Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2.

Identifiants

pubmed: 30469041
pii: S0223-5234(18)30964-4
doi: 10.1016/j.ejmech.2018.11.010
pmc: PMC6318801
mid: NIHMS1513180
pii:
doi:

Substances chimiques

Anti-Inflammatory Agents 0
Antineoplastic Agents 0
Hydroxylamines 0
IDO1 protein, human 0
IDO2 protein, human 0
Immunologic Factors 0
Indoleamine-Pyrrole 2,3,-Dioxygenase 0
Tryptophan Oxygenase EC 1.13.11.11

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

455-464

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM086482
Pays : United States
Organisme : NIGMS NIH HHS
ID : R15 GM087291
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM126297
Pays : United States
Organisme : NCI NIH HHS
ID : R01 CA191191
Pays : United States
Organisme : NCI NIH HHS
ID : R01 CA109542
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM115773
Pays : United States

Informations de copyright

Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Références

Nat Commun. 2017 Nov 22;8(1):1693
pubmed: 29167421
EBioMedicine. 2016 Dec;14:74-82
pubmed: 27889479
Eur J Med Chem. 2016 Nov 10;123:171-179
pubmed: 27475108
Cancer Res. 2005 Oct 1;65(19):8583-6
pubmed: 16204020
Front Immunol. 2014 Nov 20;5:585
pubmed: 25477879
J Am Chem Soc. 2009 Sep 16;131(36):12866-7
pubmed: 19737010
Proc Natl Acad Sci U S A. 2007 Jan 9;104(2):473-8
pubmed: 17197414
Semin Immunopathol. 2019 Jan;41(1):41-48
pubmed: 30203227
Cancer Cell. 2014 Jun 16;25(6):809-821
pubmed: 24909985
Biochem Biophys Res Commun. 2014 Jan 3;443(1):28-31
pubmed: 24269239
J Exp Med. 2013 Jul 1;210(7):1389-402
pubmed: 23752227
Cancer Res. 2017 Dec 15;77(24):6795-6811
pubmed: 29247038
Int Rev Cell Mol Biol. 2018;336:175-203
pubmed: 29413890
J Am Coll Surg. 2009 May;208(5):781-7; discussion 787-9
pubmed: 19476837
J Am Chem Soc. 2007 Dec 19;129(50):15690-701
pubmed: 18027945
Exp Cell Res. 2013 Jul 1;319(11):1644-9
pubmed: 23499742
J Med Chem. 2009 Dec 10;52(23):7364-7
pubmed: 19507862
Cancer Res. 2015 Nov 1;75(21):4651-64
pubmed: 26363006
J Immunother Cancer. 2014 Jul 07;2:21
pubmed: 25054064
Cancer Discov. 2012 Aug;2(8):722-35
pubmed: 22822050
Nat Med. 2005 Mar;11(3):312-9
pubmed: 15711557
Nature. 2011 Oct 05;478(7368):197-203
pubmed: 21976023
Biochem Pharmacol. 1995 May 17;49(10):1435-42
pubmed: 7539265
J Neurochem. 2016 Mar;136(6):1142-1154
pubmed: 26708701
J Enzyme Inhib Med Chem. 2016;31(sup1):70-78
pubmed: 27096472
J Med Chem. 2015 Oct 8;58(19):7807-19
pubmed: 26348881
Bioorg Med Chem Lett. 2012 Dec 15;22(24):7641-6
pubmed: 23122865
J Med Chem. 2013 Nov 14;56(21):8321-31
pubmed: 24099220
Cancer Immunol Res. 2015 Sep;3(9):978-85
pubmed: 26269528
Clin Cancer Res. 2016 Sep 1;22(17):4328-40
pubmed: 26979392
Bioorg Med Chem Lett. 2016 Sep 1;26(17):4330-3
pubmed: 27469130
FEBS J. 2012 Dec;279(24):4501-9
pubmed: 23083473
J Med Chem. 2015 Dec 24;58(24):9421-37
pubmed: 25970480
Proc Natl Acad Sci U S A. 2012 Feb 14;109(7):2497-502
pubmed: 22308364
J Immunol. 2016 Jun 1;196(11):4487-97
pubmed: 27183624
Int J Tryptophan Res. 2017 Mar 15;10:1178646917691938
pubmed: 28469468
ACS Med Chem Lett. 2014 Aug 21;5(10):1119-23
pubmed: 25313323
Proc Natl Acad Sci U S A. 2006 Feb 21;103(8):2611-6
pubmed: 16477023
PLoS One. 2015 Apr 16;10(4):e0122046
pubmed: 25881064
J Med Chem. 2011 Aug 11;54(15):5320-34
pubmed: 21726069
Int Immunol. 2014 Jul;26(7):357-67
pubmed: 24402311
Front Immunol. 2014 Oct 09;5:485
pubmed: 25346733
Eur J Med Chem. 2016 Jan 27;108:564-576
pubmed: 26717206

Auteurs

Maria Winters (M)

Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA, 19010, USA.

James B DuHadaway (JB)

Lankenau Institute for Medical Research, 100 Lancaster Ave, Wynnewood, PA 19096, USA.

Khoa N Pham (KN)

Department of Physiology and Biophysics, Albert Einstein College of Medicine, 1300 Morris Park Avenue, Bronx, NY 10461, United States.

Ariel Lewis-Ballester (A)

Department of Physiology and Biophysics, Albert Einstein College of Medicine, 1300 Morris Park Avenue, Bronx, NY 10461, United States.

Shorouk Badir (S)

Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA, 19010, USA.

Jenny Wai (J)

Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA, 19010, USA.

Eesha Sheikh (E)

Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA, 19010, USA.

Syun-Ru Yeh (SR)

Department of Physiology and Biophysics, Albert Einstein College of Medicine, 1300 Morris Park Avenue, Bronx, NY 10461, United States.

George C Prendergast (GC)

Lankenau Institute for Medical Research, 100 Lancaster Ave, Wynnewood, PA 19096, USA; Department of Pathology, Anatomy & Cell Biology and, Philadelphia, PA 19104, USA; Kimmel Cancer Center, Thomas Jefferson University, Philadelphia, PA 19104, USA. Electronic address: prendergast@limr.org.

Alexander J Muller (AJ)

Lankenau Institute for Medical Research, 100 Lancaster Ave, Wynnewood, PA 19096, USA; Kimmel Cancer Center, Thomas Jefferson University, Philadelphia, PA 19104, USA. Electronic address: muller@limr.org.

William P Malachowski (WP)

Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA, 19010, USA. Electronic address: wmalacho@brynmawr.edu.

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female
Humans United States Aged Cross-Sectional Studies Medicare Part C
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH