Discovery and Optimization of Rationally Designed Bicyclic Inhibitors of Human Arginase to Enhance C

Mitcheltree, Matthew J.; Li, Derun; Achab, Abdelghani; Beard, Adam; Chakravarthy, Kalyan; Cheng, Mangeng; Cho, Hyelim; Eangoor, Padmanabhan; Fan, Peter; Gathiaka, Symon; Kim, Hai-Young; Lesburg, Charles A.; Lyons, Thomas W.; Martinot, Theodore A.; Miller, J. Richard; McMinn, Spencer; O?Neil, Jennifer; Palani, Anandan; Palte, Rachel L.; Sauri, Josep; Sloman, David L.; Zhang, Hongjun; Cumming, Jared N.; Fischer, Christian

doi:10.1021/acsmedchemlett.0c00058

Discovery and Optimization of Rationally Designed Bicyclic Inhibitors of Human Arginase to Enhance C

Journal Article · Sun Mar 01 04:00:00 EST 2020 · ACS Med. Chem. Lett.

DOI:https://doi.org/10.1021/acsmedchemlett.0c00058· OSTI ID:1833662

Mitcheltree, Matthew J.; Li, Derun; Achab, Abdelghani; Beard, Adam; Chakravarthy, Kalyan; Cheng, Mangeng; Cho, Hyelim; Eangoor, Padmanabhan; Fan, Peter; Gathiaka, Symon; Kim, Hai-Young; Lesburg, Charles A.; Lyons, Thomas W.; Martinot, Theodore A.; Miller, J. Richard; McMinn, Spencer; O?Neil, Jennifer; Palani, Anandan; Palte, Rachel L.; Sauri, Josep more »

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; INDUSTRY

OSTI ID:: 1833662

Journal Information:: ACS Med. Chem. Lett., Journal Name: ACS Med. Chem. Lett. Journal Issue: (4) Vol. 11

Country of Publication:: United States

Language:: ENGLISH

References (28)

Elevated Serum Arginase Activity Levels in Patients with Breast Cancer Polat, Muhammet FevzI; TaysI, SeyIthan; Polat, SevIn� Surgery Today, Vol. 33, Issue 9 https://doi.org/10.1007/s00595-002-2563-2	journal	September 2003
Getting Across the Cell Membrane: An Overview for Small Molecules, Peptides, and Proteins Yang, Nicole J.; Hinner, Marlon J. Site-Specific Protein Labeling https://doi.org/10.1007/978-1-4939-2272-7_3	book	December 2014
Applications of Fluorine in Medicinal Chemistry Gillis, Eric P.; Eastman, Kyle J.; Hill, Matthew D. Journal of Medicinal Chemistry, Vol. 58, Issue 21 https://doi.org/10.1021/acs.jmedchem.5b00258	journal	July 2015
Discovery of ( R )-2-Amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic Acid and Congeners As Highly Potent Inhibitors of Human Arginases I and II for Treatment of Myocardial Reperfusion Injury Van Zandt, Michael C.; Whitehouse, Darren L.; Golebiowski, Adam Journal of Medicinal Chemistry, Vol. 56, Issue 6 https://doi.org/10.1021/jm400014c	journal	March 2013
Arginase I Production in the Tumor Microenvironment by Mature Myeloid Cells Inhibits T-Cell Receptor Expression and Antigen-Specific T-Cell Responses Rodriguez, Paulo C.; Quiceno, David G.; Zabaleta, Jovanny Cancer Research, Vol. 64, Issue 16 https://doi.org/10.1158/0008-5472.CAN-04-0465	journal	August 2004
Targeting Metalloenzymes for Therapeutic Intervention Chen, Allie Y.; Adamek, Rebecca N.; Dick, Benjamin L. Chemical Reviews, Vol. 119, Issue 2 https://doi.org/10.1021/acs.chemrev.8b00201	journal	September 2018
Synthesis of quaternary α-amino acid-based arginase inhibitors via the Ugi reaction Golebiowski, Adam; Whitehouse, Darren; Beckett, R. Paul Bioorganic & Medicinal Chemistry Letters, Vol. 23, Issue 17 https://doi.org/10.1016/j.bmcl.2013.06.092	journal	September 2013
Arginase: an emerging key player in the mammalian immune system: Arginase in the immune system Munder, Markus British Journal of Pharmacology, Vol. 158, Issue 3 https://doi.org/10.1111/j.1476-5381.2009.00291.x	journal	September 2009
Design of Ester Prodrugs to Enhance Oral Absorption of Poorly Permeable Compounds: Challenges to the Discovery Scientist Beaumont, Kevin; Webster, Robert; Gardner, Iain Current Drug Metabolism, Vol. 4, Issue 6 https://doi.org/10.2174/1389200033489253	journal	December 2003
L-arginine metabolism in myeloid cells controls T-lymphocyte functions Bronte, Vincenzo; Serafini, Paolo; Mazzoni, Alessandra Trends in Immunology, Vol. 24, Issue 6 https://doi.org/10.1016/S1471-4906(03)00132-7	journal	June 2003
Palladium-Catalyzed Allylic Alkylation of Simple Ketones with Allylic Alcohols and Its Mechanistic Study Huo, Xiaohong; Yang, Guoqiang; Liu, Delong Angewandte Chemie International Edition, Vol. 53, Issue 26 https://doi.org/10.1002/anie.201403410	journal	May 2014
l-Arginine Consumption by Macrophages Modulates the Expression of CD3ζ Chain in T Lymphocytes Rodriguez, Paulo C.; Zea, Arnold H.; DeSalvo, Joanna The Journal of Immunology, Vol. 171, Issue 3 https://doi.org/10.4049/jimmunol.171.3.1232	journal	July 2003
A Spectrophotometric Assay of Arginase Han, Shoufa; Viola, Ronald E. Analytical Biochemistry, Vol. 295, Issue 1 https://doi.org/10.1006/abio.2001.5189	journal	August 2001
Arginase in patients with breast cancer Porembska, Zofia; Luboiński, Grzegorz; Chrzanowska, Alicja Clinica Chimica Acta, Vol. 328, Issue 1-2 https://doi.org/10.1016/S0009-8981(02)00391-1	journal	February 2003
Targeting Intestinal Transporters for Optimizing Oral Drug Absorption V. Varma, Manthena; M. Ambler, Catherine; Ullah, Mohammad Current Drug Metabolism, Vol. 11, Issue 9 https://doi.org/10.2174/138920010794328850	journal	November 2010
Suppression of Myeloid Cell Arginase Activity leads to Therapeutic Response in a NSCLC Mouse Model by Activating Anti-Tumor Immunity Miret, Juan J.; Kirschmeier, Paul; Koyama, Shohei Journal for ImmunoTherapy of Cancer, Vol. 7, Issue 1 https://doi.org/10.1186/s40425-019-0504-5	journal	February 2019
Discovery of N -Substituted 3-Amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic Acids as Highly Potent Third-Generation Inhibitors of Human Arginase I and II Van Zandt, Michael C.; Jagdmann, G. Erik; Whitehouse, Darren L. Journal of Medicinal Chemistry, Vol. 62, Issue 17 https://doi.org/10.1021/acs.jmedchem.9b00931	journal	August 2019
Inhibition of arginase by CB-1158 blocks myeloid cell-mediated immune suppression in the tumor microenvironment Steggerda, Susanne M.; Bennett, Mark K.; Chen, Jason Journal for ImmunoTherapy of Cancer, Vol. 5, Issue 1 https://doi.org/10.1186/s40425-017-0308-4	journal	December 2017
Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design Meanwell, Nicholas A. Journal of Medicinal Chemistry, Vol. 61, Issue 14 https://doi.org/10.1021/acs.jmedchem.7b01788	journal	February 2018
Dual Palladium- and Proline-Catalyzed Allylic Alkylation of Enolizable Ketones and Aldehydes with Allylic Alcohols Usui, Ippei; Schmidt, Stefan; Breit, Bernhard Organic Letters, Vol. 11, Issue 6 https://doi.org/10.1021/ol9001812	journal	February 2009
Predicting and Tuning Physicochemical Properties in Lead Optimization: Amine Basicities Morgenthaler, Martin; Schweizer, Eliane; Hoffmann-Röder, Anja ChemMedChem, Vol. 2, Issue 8 https://doi.org/10.1002/cmdc.200700059	journal	August 2007
Regulation of arginase I activity and expression by both PD-1 and CTLA-4 on the myeloid-derived suppressor cells Liu, Yu; Yu, Yinyan; Yang, Suguang Cancer Immunology, Immunotherapy, Vol. 58, Issue 5 https://doi.org/10.1007/s00262-008-0591-5	journal	October 2008
Comprehensive analysis of the clinical immuno-oncology landscape Tang, J.; Shalabi, A.; Hubbard-Lucey, V. M. Annals of Oncology, Vol. 29, Issue 1 https://doi.org/10.1093/annonc/mdx755	journal	January 2018
Serum Arginase Level in Patients with Gastric Cancer Wu, Chew-Wun; Chi, Chin-Wen; Lin, En-Chung Journal of Clinical Gastroenterology, Vol. 18, Issue 1 https://doi.org/10.1097/00004836-199401000-00019	journal	January 1994
Arginase Inhibitors: A Rational Approach Over One Century: AN EXHAUSTIVE REVIEW OF ARGINASE INHIBITORS Pudlo, Marc; Demougeot, Céline; Girard-Thernier, Corine Medicinal Research Reviews, Vol. 37, Issue 3 https://doi.org/10.1002/med.21419	journal	November 2016
Crystal structure of human arginase I at 1.29-A resolution and exploration of inhibition in the immune response Di Costanzo, L.; Sabio, G.; Mora, A. Proceedings of the National Academy of Sciences, Vol. 102, Issue 37 https://doi.org/10.1073/pnas.0504027102	journal	September 2005
Binding of α,α-Disubstituted Amino Acids to Arginase Suggests New Avenues for Inhibitor Design Ilies, Monica; Di Costanzo, Luigi; Dowling, Daniel P. Journal of Medicinal Chemistry, Vol. 54, Issue 15 https://doi.org/10.1021/jm200443b	journal	August 2011
Fundamental Mechanisms of Immune Checkpoint Blockade Therapy Wei, Spencer C.; Duffy, Colm R.; Allison, James P. Cancer Discovery, Vol. 8, Issue 9 https://doi.org/10.1158/2159-8290.CD-18-0367	journal	August 2018

Similar Records

Discovery and Optimization of Rationally Designed Bicyclic Inhibitors of Human Arginase to Enhance C

Journal Article · Sat Feb 29 23:00:00 EST 2020 · ACS Med. Chem. Lett. · OSTI ID:1836744

Discovery, Design, and Optimization of Isoxazole Azepine BET Inhibitors

Journal Article · Mon Oct 07 00:00:00 EDT 2013 · ACS Med. Chem. Lett. · OSTI ID:1095375

Optimization of Fused Bicyclic Allosteric SHP2 Inhibitors

Journal Article · Sun Jan 27 19:00:00 EST 2019 · Journal of Medicinal Chemistry · OSTI ID:1503706

Discovery and Optimization of Rationally Designed Bicyclic Inhibitors of Human Arginase to Enhance C

Citation Formats

References (28)

Similar Records

Related Subjects