Structural basis of binding and inhibition of ornithine decarboxylase by 1-amino-oxy-3-aminopropane

Zhou, X. Edward; Suino-Powell, Kelly; Schultz, Chad R.; Aleiwi, Bilal; Brunzelle, Joseph S.; Lamp, Jared; Vega, Irving E.; Ellsworth, Edmund; Bachmann, Andre S.; Melcher, Karsten

doi:10.1042/BCJ20210647

Structural basis of binding and inhibition of ornithine decarboxylase by 1-amino-oxy-3-aminopropane

Journal Article · 01 December 2021 · Biochem. J.

DOI:https://doi.org/10.1042/BCJ20210647· OSTI ID:1841242

Zhou, X. Edward; Suino-Powell, Kelly; Schultz, Chad R.; Aleiwi, Bilal; Brunzelle, Joseph S.; Lamp, Jared; Vega, Irving E.; Ellsworth, Edmund; Bachmann, Andre S.; Melcher, Karsten

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

Sponsoring Organization:: DOE - Office Of Science; OTHER

OSTI ID:: 1841242

Journal Information:: Biochem. J., Journal Name: Biochem. J. Journal Issue: (23) Vol. 478

Country of Publication:: United States

Language:: ENGLISH

References (40)

Crystal structure of human ornithine decarboxylase at 2.1 å resolution: structural insights to antizyme binding Almrud, Jeffrey J.; Oliveira, Marcos A.; Kern, Andrew D. Journal of Molecular Biology, Vol. 295, Issue 1 https://doi.org/10.1006/jmbi.1999.3331	journal	January 2000
c-myc Transactivates the Ornithine Decarboxylase Gene Bello-Fernandez, C.; Cleveland, J. L. Mechanisms in B-Cell Neoplasia 1992 https://doi.org/10.1007/978-3-642-77633-5_56	book	January 1992
Pharmacological properties of the ornithine decarboxylase inhibitor 3-aminooxy-1-propanamine and several structural analogues Mett, Helmut; Stanek, Jaroslav; Lopez-Ballester, Juan A. Cancer Chemotherapy and Pharmacology, Vol. 32, Issue 1 https://doi.org/10.1007/BF00685874	journal	January 1993
Hydroxylamine-containing inhibitors of polyamine biosynthesis and impairment of colon cancer cell growth11Abbreviations: AMA, S-(5′-deoxy-5′-adenosyl)-methylthioethyl-hydroxylamine; APA, 1-aminooxy-3-aminopropane; DFMO, alpha-difluoromethylornithine; DMEM, Dulbecco’s modified Eagle’s medium; DTT, dithiothreitol; EGF, epidermal growth factor; 5-FU, 5-fluorouracil; LDH, lactate dehydrogenase; MGBG, methyl-bisguanylhydrazone; SAM, S-adenosylmethionine; SAMDC, S-adenosylmethionine decarboxylase; and ODC, ornithine decarboxylase. Milovica, Vladan; Turchanowa, Lyudmila; Khomutov, Alex R. Biochemical Pharmacology, Vol. 61, Issue 2 https://doi.org/10.1016/S0006-2952(00)00549-9	journal	January 2001
1-Aminooxy-3-aminopropane reversibly prevents the proliferation of cultured baby hamster kidney cells by interfering with polyamine synthesis. Hyvönen, T.; Alakuijala, L.; Andersson, L. Journal of Biological Chemistry, Vol. 263, Issue 23 https://doi.org/10.1016/S0021-9258(18)37933-X	journal	August 1988
Multiple DNA elements responsible for transcriptional regulation of the ornithine decarboxylase gene by protein kinase A. Abrahamsen, M. S.; Li, R. S.; Dietrich-Goetz, W. Journal of Biological Chemistry, Vol. 267, Issue 26 https://doi.org/10.1016/S0021-9258(19)37041-3	journal	September 1992
Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial Priotto, Gerardo; Kasparian, Serena; Mutombo, Wilfried The Lancet, Vol. 374, Issue 9683 https://doi.org/10.1016/S0140-6736(09)61117-X	journal	July 2009
Ornithine decarboxylase antizyme: a novel type of regulatory protein Hayashi, Shin-ichi; Murakami, Yasuko; Matsufuji, Senya Trends in Biochemical Sciences, Vol. 21, Issue 1 https://doi.org/10.1016/S0968-0004(06)80024-1	journal	January 1996
Structure of mammalian ornithine decarboxylase at 1.6 Å resolution: stereochemical implications of PLP-dependent amino acid decarboxylases Kern, Andrew D.; Oliveira, Marcos A.; Coffino, Philip Structure, Vol. 7, Issue 5 https://doi.org/10.1016/S0969-2126(99)80073-2	journal	May 1999
Selective delivery of 2-hydroxy APA to Trypanosoma brucei using the melamine motif Klee, Nina; Wong, Pui Ee; Baragaña, Beatriz Bioorganic & Medicinal Chemistry Letters, Vol. 20, Issue 15 https://doi.org/10.1016/j.bmcl.2010.06.070	journal	August 2010
Structural Insights into Substrate Recognition and Activity Regulation of the Key Decarboxylase SbnH in Staphyloferrin B Biosynthesis Tang, Jieyu; Ju, Yingchen; Gu, Qiong Journal of Molecular Biology, Vol. 431, Issue 24 https://doi.org/10.1016/j.jmb.2019.10.009	journal	December 2019
Altering the Reaction Specificity of Eukaryotic Ornithine Decarboxylase ^† ^, ^‡ Jackson, Laurie K.; Brooks, Harold B.; Osterman, Andrei L. Biochemistry, Vol. 39, Issue 37 https://doi.org/10.1021/bi001209s	journal	September 2000
X-ray Structure of Ornithine Decarboxylase from Trypanosoma brucei : The Native Structure and the Structure in Complex with α-Difluoromethylornithine ^† ^, ^‡ Grishin, Nick V.; Osterman, Andrei L.; Brooks, Harold B. Biochemistry, Vol. 38, Issue 46 https://doi.org/10.1021/bi9915115	journal	November 1999
LigPlot+: Multiple Ligand–Protein Interaction Diagrams for Drug Discovery Laskowski, Roman A.; Swindells, Mark B. Journal of Chemical Information and Modeling, Vol. 51, Issue 10 https://doi.org/10.1021/ci200227u	journal	October 2011
2-Substituted 3-(aminooxy)propanamines as inhibitors of ornithine decarboxylase: synthesis and biological activity Stanek, Jaroslav; Frei, Joerg; Mett, Helmut Journal of Medicinal Chemistry, Vol. 35, Issue 8 https://doi.org/10.1021/jm00086a003	journal	April 1992
Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases Casero, Robert A.; Marton, Laurence J. Nature Reviews Drug Discovery, Vol. 6, Issue 5 https://doi.org/10.1038/nrd2243	journal	May 2007
Polyamine metabolism and cancer: treatments, challenges and opportunities Casero, Robert A.; Murray Stewart, Tracy; Pegg, Anthony E. Nature Reviews Cancer, Vol. 18, Issue 11 https://doi.org/10.1038/s41568-018-0050-3	journal	September 2018
Maintenance DFMO Increases Survival in High Risk Neuroblastoma Sholler, Giselle L. Saulnier; Ferguson, William; Bergendahl, Genevieve Scientific Reports, Vol. 8, Issue 1 https://doi.org/10.1038/s41598-018-32659-w	journal	September 2018
Structural basis of Ornithine Decarboxylase inactivation and accelerated degradation by polyamine sensor Antizyme1 Wu, Donghui; Kaan, Hung Yi Kristal; Zheng, Xiaoxia Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep14738	journal	October 2015
A structural insight into the inhibition of human and Leishmania donovani ornithine decarboxylases by 1-amino-oxy-3-aminopropane Dufe, Veronica T.; Ingner, Daniel; Heby, Olle Biochemical Journal, Vol. 405, Issue 2 https://doi.org/10.1042/BJ20070188	journal	June 2007
Structural basis of antizyme-mediated regulation of polyamine homeostasis Wu, Hsiang-Yi; Chen, Shin-Fu; Hsieh, Ju-Yi Proceedings of the National Academy of Sciences, Vol. 112, Issue 36 https://doi.org/10.1073/pnas.1508187112	journal	August 2015
Induction of a protein inhibitor to ornithine decarboxylase by the end products of its reaction. Heller, J. S.; Fong, W. F.; Canellakis, E. S. Proceedings of the National Academy of Sciences, Vol. 73, Issue 6 https://doi.org/10.1073/pnas.73.6.1858	journal	June 1976
The ornithine decarboxylase gene is a transcriptional target of c-Myc. Bello-Fernandez, C.; Packham, G.; Cleveland, J. L. Proceedings of the National Academy of Sciences, Vol. 90, Issue 16 https://doi.org/10.1073/pnas.90.16.7804	journal	August 1993
Acidic Residues Important for Substrate Binding and Cofactor Reactivity in Eukaryotic Ornithine Decarboxylase Identified by Alanine Scanning Mutagenesis Osterman, Andrei L.; Kinch, Lisa N.; Grishin, Nick V. Journal of Biological Chemistry, Vol. 270, Issue 20 https://doi.org/10.1074/jbc.270.20.11797	journal	May 1995
Multisite Phosphorylation of Ornithine Decarboxylase in Transformed Macrophages Results in Increased Intracellular Enzyme Stability and Catalytic Efficiency Reddy, SundeepG.; Mcllheran, SarahM.; Cochran, BarbaraJ. Journal of Biological Chemistry, Vol. 271, Issue 40 https://doi.org/10.1074/jbc.271.40.24945	journal	October 1996
X-ray Structure Determination of Trypanosoma brucei Ornithine Decarboxylase Bound to d-Ornithine and to G418 Jackson, Laurie K.; Goldsmith, Elizabeth J.; Phillips, Margaret A. Journal of Biological Chemistry, Vol. 278, Issue 24 https://doi.org/10.1074/jbc.M300188200	journal	June 2003
Regulation of Ornithine Decarboxylase Pegg, Anthony E. Journal of Biological Chemistry, Vol. 281, Issue 21 https://doi.org/10.1074/jbc.R500031200	journal	May 2006
Alternative pathways utilize or circumvent putrescine for biosynthesis of putrescine-containing rhizoferrin Li, Bin; Deng, Xiaoyi; Kim, Sok Ho Journal of Biological Chemistry, Vol. 296 https://doi.org/10.1074/jbc.RA120.016738	journal	January 2021
Polyamine synthesis as a target of MYC oncogenes Bachmann, André S.; Geerts, Dirk Journal of Biological Chemistry, Vol. 293, Issue 48 https://doi.org/10.1074/jbc.TM118.003336	journal	November 2018
The antizyme family: Polyamines and beyond Mangold, Ursula IUBMB Life (International Union of Biochemistry and Molecular Biology: Life), Vol. 57, Issue 10 https://doi.org/10.1080/15216540500307031	journal	October 2005
Nifurtimox-Eflornithine Combination Therapy for Second-Stage Gambiense Human African Trypanosomiasis: Médecins Sans Frontières Experience in the Democratic Republic of the Congo Alirol, Emilie; Schrumpf, David; Amici Heradi, Josué Clinical Infectious Diseases, Vol. 56, Issue 2 https://doi.org/10.1093/cid/cis886	journal	October 2012
PHENIX: a comprehensive Python-based system for macromolecular structure solution Adams, Paul D.; Afonine, Pavel V.; Bunkóczi, Gábor Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2, p. 213-221 https://doi.org/10.1107/S0907444909052925	journal	January 2010
Features and development of Coot Emsley, P.; Lohkamp, B.; Scott, W. G. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 4 https://doi.org/10.1107/S0907444910007493	journal	March 2010
iMOSFLM : a new graphical interface for diffraction-image processing with MOSFLM Battye, T. Geoff G.; Kontogiannis, Luke; Johnson, Owen Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444910048675	journal	March 2011
Mouse ornithine decarboxylase is phosphorylated by casein kinase-II at a predominant single location (serine 303) Rosenberg-Hasson, Yael; Strumpf, Dan; Kahana, Chaim European Journal of Biochemistry, Vol. 197, Issue 2 https://doi.org/10.1111/j.1432-1033.1991.tb15927.x	journal	April 1991
Crystal Structures and Solution Studies of Oxime Adducts of Mitochondrial Aspartate Aminotransferase Markovic-Housley, Zora; Schirmer, Tilman; Hohenester, Erhard European Journal of Biochemistry, Vol. 236, Issue 3 https://doi.org/10.1111/j.1432-1033.1996.01025.x	journal	March 1996
Prevention of Rapid Intracellular Degradation of ODC by a Carboxyl-Terminal Truncation Ghoda, L.; van Daalen Wetters, T.; Macrae, M. Science, Vol. 243, Issue 4897 https://doi.org/10.1126/science.2928784	journal	March 1989
Difluoromethylornithine Plus Sulindac for the Prevention of Sporadic Colorectal Adenomas: A Randomized Placebo-Controlled, Double-Blind Trial Meyskens, Frank L.; McLaren, Christine E.; Pelot, Daniel Cancer Prevention Research, Vol. 1, Issue 1 https://doi.org/10.1158/1940-6207.CAPR-08-0042	journal	April 2008
A Phase I Trial of DFMO Targeting Polyamine Addiction in Patients with Relapsed/Refractory Neuroblastoma Saulnier Sholler, Giselle L.; Gerner, Eugene W.; Bergendahl, Genevieve PLOS ONE, Vol. 10, Issue 5 https://doi.org/10.1371/journal.pone.0127246	journal	May 2015
Translational development of difluoromethylornithine (DFMO) for the treatment of neuroblastoma Bassiri, Hamid; Benavides, Adriana; Haber, Michelle Translational Pediatrics, Vol. 4, Issue 3 https://doi.org/10.3978/j.issn.2224-4336.2015.04.06	journal	July 2015

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