Rational Design, Synthesis, and Mechanism of (3S,4R)-3-Amino-4-(difluoromethyl)cyclopent-1-ene-1-car

Zhu, Wei; Butrin, Arseniy; Melani, Rafael D.; Doubleday, Peter F.; Ferreira, Glaucio Monteiro; Tavares, Mauricio T.; Mohammad, Thahani S.Habeeb; Beaupre, Brett A.; Kelleher, Neil L.; Moran, Graham R.; Liu, Dali; Silverman, Richard B.

doi:10.1021/jacs.2c00924

Rational Design, Synthesis, and Mechanism of (3S,4R)-3-Amino-4-(difluoromethyl)cyclopent-1-ene-1-car

Journal Article · 28 February 2022 · J. Am. Chem. Soc.

DOI:https://doi.org/10.1021/jacs.2c00924· OSTI ID:1867473

Zhu, Wei; Butrin, Arseniy; Melani, Rafael D.; Doubleday, Peter F.; Ferreira, Glaucio Monteiro; Tavares, Mauricio T.; Mohammad, Thahani S.Habeeb; Beaupre, Brett A.; Kelleher, Neil L.; Moran, Graham R.; Liu, Dali; Silverman, Richard B.

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

Sponsoring Organization:: DOE - Office Of Science; NIH

OSTI ID:: 1867473

Journal Information:: J. Am. Chem. Soc., Journal Name: J. Am. Chem. Soc. Journal Issue: (12) Vol. 144

Country of Publication:: United States

Language:: ENGLISH

References (39)

Mechanism-Based Design of 3-Amino-4-Halocyclopentenecarboxylic Acids as Inactivators of GABA Aminotransferase Shen, Sida; Doubleday, Peter F.; Weerawarna, Pathum M. ACS Medicinal Chemistry Letters, Vol. 11, Issue 10 https://doi.org/10.1021/acsmedchemlett.9b00672	journal	February 2020
The Proline Regulatory Axis and Cancer Phang, James Ming; Liu, Wei; Hancock, Chad Frontiers in Oncology, Vol. 2 https://doi.org/10.3389/fonc.2012.00060	journal	January 2012
Management of hepatocellular carcinoma Fitzmorris, P.; Shoreibah, M.; Anand, B. S. Journal of Cancer Research and Clinical Oncology, Vol. 141, Issue 5 https://doi.org/10.1007/s00432-014-1806-0	journal	August 2014
Ornithine aminotransferase promoted the proliferation and metastasis of non‐small cell lung cancer via upregulation of miR‐21 Liu, Yanfeng; Wu, Lei; Li, Kai Journal of Cellular Physiology, Vol. 234, Issue 8 https://doi.org/10.1002/jcp.27939	journal	December 2018
Design and Mechanism of ( S )-3-Amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic Acid, a Highly Potent γ-Aminobutyric Acid Aminotransferase Inactivator for the Treatment of Addiction Juncosa, Jose I.; Takaya, Kenji; Le, Hoang V. Journal of the American Chemical Society, Vol. 140, Issue 6 https://doi.org/10.1021/jacs.7b10965	journal	January 2018
Mechanism of Inactivation of γ-Aminobutyric Acid Aminotransferase by (1 S ,3 S )-3-Amino-4-difluoromethylene-1-cyclopentanoic Acid (CPP-115) Lee, Hyunbeom; Doud, Emma H.; Wu, Rui Journal of the American Chemical Society, Vol. 137, Issue 7 https://doi.org/10.1021/ja512299n	journal	February 2015
Mechanism of Inactivation of Ornithine Aminotransferase by (1 S ,3 S )-3-Amino-4-(hexafluoropropan-2-ylidenyl)cyclopentane-1-carboxylic Acid Moschitto, Matthew J.; Doubleday, Peter F.; Catlin, Daniel S. Journal of the American Chemical Society, Vol. 141, Issue 27 https://doi.org/10.1021/jacs.9b03254	journal	June 2019
Remarkable and Unexpected Mechanism for ( S )-3-Amino-4-(difluoromethylenyl)cyclohex-1-ene-1-carboxylic Acid as a Selective Inactivator of Human Ornithine Aminotransferase Zhu, Wei; Doubleday, Peter F.; Butrin, Arseniy Journal of the American Chemical Society, Vol. 143, Issue 21 https://doi.org/10.1021/jacs.1c03572	journal	May 2021
The Properties, Developmental Formation, and Estrogen Induction of Ornithine Aminotransferase in Rat Tissues Herzfeld, A.; Knox, W. E. Journal of Biological Chemistry, Vol. 243, Issue 12 https://doi.org/10.1016/S0021-9258(18)93310-7	journal	June 1968
Ornithine Aminotransferase, an Important Glutamate-Metabolizing Enzyme at the Crossroads of Multiple Metabolic Pathways Ginguay, Antonin; Cynober, Luc; Curis, Emmanuel Biology, Vol. 6, Issue 4 https://doi.org/10.3390/biology6010018	journal	March 2017
How many water molecules are detected in X-ray protein crystal structures? Gnesi, Marco; Carugo, Oliviero Journal of Applied Crystallography, Vol. 50, Issue 1 https://doi.org/10.1107/S1600576716018719	journal	February 2017
Screening for hepatocellular carcinoma: The rationale for the American Association for the Study of Liver Diseases recommendations Sherman, Morris; Bruix, Jordi; Porayko, Michael Hepatology, Vol. 56, Issue 3 https://doi.org/10.1002/hep.25869	journal	July 2012
Synthesis of ( S )-3-Amino-4-(difluoromethylenyl)-cyclopent-1-ene-1-carboxylic Acid (OV329), a Potent Inactivator of γ-Aminobutyric Acid Aminotransferase Moschitto, Matthew J.; Silverman, Richard B. Organic Letters, Vol. 20, Issue 15 https://doi.org/10.1021/acs.orglett.8b01872	journal	July 2018
Mechanism of Inactivation of GABA Aminotransferase by ( E )- and ( Z )-(1 S ,3 S )-3-Amino-4-fluoromethylenyl-1-cyclopentanoic Acid Lee, Hyunbeom; Le, Hoang V.; Wu, Rui ACS Chemical Biology, Vol. 10, Issue 9 https://doi.org/10.1021/acschembio.5b00212	journal	July 2015
Theoretical and Mechanistic Validation of Global Kinetic Parameters of the Inactivation of GABA Aminotransferase by OV329 and CPP-115 Weerawarna, Pathum M.; Moschitto, Matthew J.; Silverman, Richard B. ACS Chemical Biology, Vol. 16, Issue 4 https://doi.org/10.1021/acschembio.0c00784	journal	March 2021
Proline Metabolism and Microenvironmental Stress Phang, James M.; Liu, Wei; Zabirnyk, Olga Annual Review of Nutrition, Vol. 30, Issue 1 https://doi.org/10.1146/annurev.nutr.012809.104638	journal	July 2010
New targets of β-catenin signaling in the liver are involved in the glutamine metabolism Cadoret, Axelle; Ovejero, Christine; Terris, Benoit Oncogene, Vol. 21, Issue 54 https://doi.org/10.1038/sj.onc.1206118	journal	November 2002
When proteins are completely hydrated in crystals Carugo, Oliviero International Journal of Biological Macromolecules, Vol. 89 https://doi.org/10.1016/j.ijbiomac.2016.04.061	journal	August 2016
The metabolism of proline, a stress substrate, modulates carcinogenic pathways Phang, James M.; Donald, Steven P.; Pandhare, Jui Amino Acids, Vol. 35, Issue 4 https://doi.org/10.1007/s00726-008-0063-4	journal	April 2008
A Remarkable Difference That One Fluorine Atom Confers on the Mechanisms of Inactivation of Human Ornithine Aminotransferase by Two Cyclohexene Analogues of γ-Aminobutyric Acid Zhu, Wei; Doubleday, Peter F.; Catlin, Daniel S. Journal of the American Chemical Society, Vol. 142, Issue 10 https://doi.org/10.1021/jacs.0c00193	journal	March 2020
PHENIX : building new software for automated crystallographic structure determination Adams, Paul D.; Grosse-Kunstleve, Ralf W.; Hung, Li-Wei Acta Crystallographica Section D Biological Crystallography, Vol. 58, Issue 11 https://doi.org/10.1107/S0907444902016657	journal	October 2002
Design and Mechanism of GABA Aminotransferase Inactivators. Treatments for Epilepsies and Addictions Silverman, Richard B. Chemical Reviews, Vol. 118, Issue 7 https://doi.org/10.1021/acs.chemrev.8b00009	journal	February 2018
Fluorinated Conformationally Restricted γ-Aminobutyric Acid Aminotransferase Inhibitors Lu, Hejun; Silverman, Richard B. Journal of Medicinal Chemistry, Vol. 49, Issue 25 https://doi.org/10.1021/jm0608715	journal	November 2006
Sorafenib for Treatment of Hepatocellular Carcinoma: A Survival Analysis From the South American Liver Research Network Leathers, James S.; Balderramo, Domingo; Prieto, John Journal of Clinical Gastroenterology, Vol. 53, Issue 6 https://doi.org/10.1097/MCG.0000000000001085	journal	January 2019
Hepatocellular carcinoma: a global view Yang, Ju Dong; Roberts, Lewis R. Nature Reviews Gastroenterology & Hepatology, Vol. 7, Issue 8 https://doi.org/10.1038/nrgastro.2010.100	journal	July 2010
Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor Pan, Yue; Qiu, Jian; Silverman, Richard B. Journal of Medicinal Chemistry, Vol. 46, Issue 25 https://doi.org/10.1021/jm034162s	journal	November 2003
2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics Singh, Rohit; Vince, Robert Chemical Reviews, Vol. 112, Issue 8 https://doi.org/10.1021/cr2004822	journal	May 2012
Emerging tyrosine kinase inhibitors for the treatment of hepatocellular carcinoma de Rosamel, Laure; Blanc, Jean-Frederic Expert Opinion on Emerging Drugs, Vol. 22, Issue 2 https://doi.org/10.1080/14728214.2017.1336538	journal	April 2017
Understanding the Warburg Effect: The Metabolic Requirements of Cell Proliferation Vander Heiden, M. G.; Cantley, L. C.; Thompson, C. B. Science, Vol. 324, Issue 5930 https://doi.org/10.1126/science.1160809	journal	May 2009
Hepatocellular Carcinoma: A Global Disease in Need of Individualized Treatment Strategies Personeni, Nicola; Rimassa, Lorenza Journal of Oncology Practice, Vol. 13, Issue 6 https://doi.org/10.1200/JOP.2017.024604	journal	June 2017
Theoretical calculation of the pKa values of some drugs in aqueous solution Ghalami-Choobar, Bahram; Dezhampanah, Hamid; Nikparsa, Paria International Journal of Quantum Chemistry, Vol. 112, Issue 10 https://doi.org/10.1002/qua.23211	journal	August 2011
Chemical, Physical, and Morphological Properties of Ornithine Aminotransferase from Rat Liver Peraino, C.; Bunville, L. G.; Tahmisian, T. N. Journal of Biological Chemistry, Vol. 244, Issue 9 https://doi.org/10.1016/S0021-9258(19)78217-9	journal	May 1969
Management of HCC de Lope, Carlos Rodríguez; Tremosini, Silvia; Forner, Alejandro Journal of Hepatology, Vol. 56 https://doi.org/10.1016/S0168-8278(12)60009-9	journal	January 2012
Proline metabolism and cancer: emerging links to glutamine and collagen Phang, James M.; Liu, Wei; Hancock, Chad N. Current Opinion in Clinical Nutrition and Metabolic Care, Vol. 18, Issue 1 https://doi.org/10.1097/MCO.0000000000000121	journal	January 2015
Liver-targeted disruption of Apc in mice activates -catenin signaling and leads to hepatocellular carcinomas Colnot, S.; Decaens, T.; Niwa-Kawakita, M. Proceedings of the National Academy of Sciences, Vol. 101, Issue 49 https://doi.org/10.1073/pnas.0404761101	journal	November 2004
Suppression of Hepatocellular Carcinoma by Inhibition of Overexpressed Ornithine Aminotransferase Zigmond, Ehud; Ya’acov, Ami Ben; Lee, Hyunbeom ACS Medicinal Chemistry Letters, Vol. 6, Issue 8 https://doi.org/10.1021/acsmedchemlett.5b00153	journal	June 2015
Global Metabolic Profiling Identifies a Pivotal Role of Proline and Hydroxyproline Metabolism in Supporting Hypoxic Response in Hepatocellular Carcinoma Tang, Ling; Zeng, Jun; Geng, Pengyu Clinical Cancer Research, Vol. 24, Issue 2 https://doi.org/10.1158/1078-0432.CCR-17-1707	journal	October 2017
Disease Burden of Hepatocellular Carcinoma: A Global Perspective Sayiner, Mehmet; Golabi, Pegah; Younossi, Zobair M. Digestive Diseases and Sciences, Vol. 64, Issue 4 https://doi.org/10.1007/s10620-019-05537-2	journal	March 2019
(1 S , 3 S )-3-Amino-4-difluoromethylenyl-1-cyclopentanoic Acid ( CPP-115 ), a Potent γ-Aminobutyric Acid Aminotransferase Inactivator for the Treatment of Cocaine Addiction Pan, Yue; Gerasimov, Madina R.; Kvist, Trine Journal of Medicinal Chemistry, Vol. 55, Issue 1 https://doi.org/10.1021/jm201231w	journal	December 2011

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