N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum ;#945;-Glucosida

Karade, Sharanbasappa S.; Hill, Michelle L.; Kiappes, J.L.; Manne, Rajkumar; Aakula, Balakishan; Zitzmann, Nicole; Warfield, Kelly L.; Treston, Anthony M.; Mariuzza, Roy A.

doi:10.1021/acs.jmedchem.1c01377

N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum ;#945;-Glucosida

Journal Article · 01 December 2021 · J. Med. Chem.

DOI:https://doi.org/10.1021/acs.jmedchem.1c01377· OSTI ID:1839717

Karade, Sharanbasappa S.; Hill, Michelle L.; Kiappes, J.L.; Manne, Rajkumar; Aakula, Balakishan; Zitzmann, Nicole; Warfield, Kelly L.; Treston, Anthony M.; Mariuzza, Roy A.

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: DOE - Office Of Science; DOE - BASIC ENERGY SCIENCES

OSTI ID:: 1839717

Journal Information:: J. Med. Chem., Vol. 64, Issue (24)

Country of Publication:: United States

Language:: ENGLISH

References (37)

Medicinal chemistry strategies toward host targeting antiviral agents Ji, Xingyue; Li, Zhuorong Medicinal Research Reviews, Vol. 40, Issue 5 https://doi.org/10.1002/med.21664	journal	February 2020
Update on hepatitis C virus resistance to direct-acting antiviral agents Poveda, Eva; Wyles, David L.; Mena, Álvaro Antiviral Research, Vol. 108 https://doi.org/10.1016/j.antiviral.2014.05.015	journal	August 2014
Why highly effective drugs are not enough: the need for an affordable solution to eliminating HCV Hayes, C. Nelson; Chayama, Kazuaki Expert Review of Clinical Pharmacology, Vol. 10, Issue 6 https://doi.org/10.1080/17512433.2017.1313111	journal	April 2017
New pharmacological strategies to fight enveloped viruses Wisskirchen, Karin; Lucifora, Julie; Michler, Thomas Trends in Pharmacological Sciences, Vol. 35, Issue 9 https://doi.org/10.1016/j.tips.2014.06.004	journal	September 2014
Antiviral drug discovery: broad-spectrum drugs from nature Martinez, J. P.; Sasse, F.; Brönstrup, M. Natural Product Reports, Vol. 32, Issue 1 https://doi.org/10.1039/c4np00085d	journal	January 2015
HSP90: a promising broad-spectrum antiviral drug target Wang, Yiliang; Jin, Fujun; Wang, Rongze Archives of Virology, Vol. 162, Issue 11 https://doi.org/10.1007/s00705-017-3511-1	journal	August 2017
The Use of Calnexin and Calreticulin by Cellular and Viral Glycoproteins Pieren, Michel; Galli, Carmela; Denzel, Angela Journal of Biological Chemistry, Vol. 280, Issue 31 https://doi.org/10.1074/jbc.m501020200	journal	August 2005
Role of N-linked oligosaccharide recognition, glucose trimming, and calnexin in glycoprotein folding and quality control. Hammond, C.; Braakman, I.; Helenius, A. Proceedings of the National Academy of Sciences, Vol. 91, Issue 3 https://doi.org/10.1073/pnas.91.3.913	journal	February 1994
Emerging Principles for the Therapeutic Exploitation of Glycosylation Dalziel, Martin; Crispin, Max; Scanlan, Christopher N. Science, Vol. 343, Issue 6166 https://doi.org/10.1126/science.1235681	journal	January 2014
UDP-GlC:glycoprotein glucosyltransferase-glucosidase II, the ying-yang of the ER quality control D’Alessio, Cecilia; Caramelo, Julio J.; Parodi, Armando J. Seminars in Cell & Developmental Biology, Vol. 21, Issue 5 https://doi.org/10.1016/j.semcdb.2009.12.014	journal	July 2010
N -glycan processing in ER quality control Ruddock, Lloyd W.; Molinari, Maurizio Journal of Cell Science, Vol. 119, Issue 21 https://doi.org/10.1242/jcs.03225	journal	November 2006
Antiviral therapies targeting host ER alpha-glucosidases: Current status and future directions Chang, Jinhong; Block, Timothy M.; Guo, Ju-Tao Antiviral Research, Vol. 99, Issue 3 https://doi.org/10.1016/j.antiviral.2013.06.011	journal	September 2013
Iminosugars: A host-targeted approach to combat Flaviviridae infections Evans DeWald, Lisa; Starr, Chloe; Butters, Terry Antiviral Research, Vol. 184 https://doi.org/10.1016/j.antiviral.2020.104881	journal	December 2020
Synthesis, in vitro inhibitory activity, kinetic study and molecular docking of novel N -alkyl–deoxynojirimycin derivatives as potential α-glucosidase inhibitors Lin, Ping; Zeng, Jia-Cheng; Chen, Ji-Guang Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 35, Issue 1 https://doi.org/10.1080/14756366.2020.1826941	journal	January 2020
An iminosugar with potent inhibition of dengue virus infection in vivo Perry, Stuart T.; Buck, Michael D.; Plummer, Emily M. Antiviral Research, Vol. 98, Issue 1 https://doi.org/10.1016/j.antiviral.2013.01.004	journal	April 2013
Targeting Endoplasmic Reticulum α-Glucosidase I with a Single-Dose Iminosugar Treatment Protects against Lethal Influenza and Dengue Virus Infections Warfield, Kelly L.; Alonzi, Dominic S.; Hill, Johan C. Journal of Medicinal Chemistry, Vol. 63, Issue 8 https://doi.org/10.1021/acs.jmedchem.0c00067	journal	March 2020
In Vivo Therapeutic Protection against Influenza A (H1N1) Oseltamivir-Sensitive and Resistant Viruses by the Iminosugar UV-4 Stavale, Eric J.; Vu, Hong; Sampath, Aruna PLOS ONE, Vol. 10, Issue 3 https://doi.org/10.1371/journal.pone.0121662	journal	March 2015
The Iminosugar UV-4 is a Broad Inhibitor of Influenza A and B Viruses ex Vivo and in Mice Warfield, Kelly; Barnard, Dale; Enterlein, Sven Viruses, Vol. 8, Issue 3 https://doi.org/10.3390/v8030071	journal	March 2016
α-glucosidase inhibitors as host-directed antiviral agents with potential for the treatment of COVID-19 Williams, Spencer J.; Goddard-Borger, Ethan D. Biochemical Society Transactions, Vol. 48, Issue 3 https://doi.org/10.1042/bst20200505	journal	June 2020
The iminosugars celgosivir, castanospermine and UV-4 inhibit SARS-CoV-2 replication Clarke, Elizabeth C.; Nofchissey, Robert A.; Ye, Chunyan Glycobiology, Vol. 31, Issue 4 https://doi.org/10.1093/glycob/cwaa091	journal	September 2020
Synthetic heterocyclic candidates as promising α-glucosidase inhibitors: An overview Dhameja, Manoj; Gupta, Preeti European Journal of Medicinal Chemistry, Vol. 176 https://doi.org/10.1016/j.ejmech.2019.04.025	journal	August 2019
Valiolamine, a new .ALPHA.-glucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus. Kameda, Yukihiko; Asano, Naoki; Yoshikawa, Michiyo The Journal of Antibiotics, Vol. 37, Issue 11 https://doi.org/10.7164/antibiotics.37.1301	journal	January 1984
Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents Horii, Satoshi; Fukase, Hiroshi; Matsuo, Takao Journal of Medicinal Chemistry, Vol. 29, Issue 6 https://doi.org/10.1021/jm00156a023	journal	June 1986
Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis Cumpstey, Ian; Ramstadius, Clinton; Eszter Borbas, K. Bioorganic & Medicinal Chemistry Letters, Vol. 21, Issue 18 https://doi.org/10.1016/j.bmcl.2011.07.046	journal	September 2011
Structures of mammalian ER α-glucosidase II capture the binding modes of broad-spectrum iminosugar antivirals Caputo, Alessandro T.; Alonzi, Dominic S.; Marti, Lucia Proceedings of the National Academy of Sciences, Vol. 113, Issue 32 https://doi.org/10.1073/pnas.1604463113	journal	July 2016
Synthesis and Biological Characterisation of Novel N -Alkyl-Deoxynojirimycin α-Glucosidase Inhibitors Rawlings, Amy J.; Lomas, Hannah; Pilling, Adam W. ChemBioChem, Vol. 10, Issue 6 https://doi.org/10.1002/cbic.200900025	journal	April 2009
Hydrogen bonds with π-acceptors in proteins: frequencies and role in stabilizing local 3D structures11Edited by R. Huber Steiner, Thomas; Koellner, Gertraud Journal of Molecular Biology, Vol. 305, Issue 3 https://doi.org/10.1006/jmbi.2000.4301	journal	January 2001
Inhibition of endoplasmic reticulum glucosidases is required for in vitro and in vivo dengue antiviral activity by the iminosugar UV-4 Warfield, Kelly L.; Plummer, Emily M.; Sayce, Andrew C. Antiviral Research, Vol. 129 https://doi.org/10.1016/j.antiviral.2016.03.001	journal	May 2016
Human Intestinal Maltase–Glucoamylase: Crystal Structure of the N-Terminal Catalytic Subunit and Basis of Inhibition and Substrate Specificity Sim, Lyann; Quezada-Calvillo, Roberto; Sterchi, Erwin E. Journal of Molecular Biology, Vol. 375, Issue 3 https://doi.org/10.1016/j.jmb.2007.10.069	journal	January 2008
AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility Morris, Garrett M.; Huey, Ruth; Lindstrom, William Journal of Computational Chemistry, Vol. 30, Issue 16 https://doi.org/10.1002/jcc.21256	journal	December 2009
A versatile ligation-independent cloning method suitable for high-throughput expression screening applications Berrow, N. S.; Alderton, D.; Sainsbury, S. Nucleic Acids Research, Vol. 35, Issue 6 https://doi.org/10.1093/nar/gkm047	journal	March 2007
[20] Processing of X-ray diffraction data collected in oscillation mode Otwinowski, Zbyszek; Minor, Wladek Macromolecular Crystallography Part A, 307-326 https://doi.org/10.1016/s0076-6879(97)76066-x	book	January 1997
Phaser crystallographic software McCoy, Airlie J.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Journal of Applied Crystallography, Vol. 40, Issue 4 https://doi.org/10.1107/s0021889807021206	journal	July 2007
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
Towards automated crystallographic structure refinement with phenix.refine Afonine, Pavel V.; Grosse-Kunstleve, Ralf W.; Echols, Nathaniel Acta Crystallographica Section D Biological Crystallography, Vol. 68, Issue 4 https://doi.org/10.1107/s0907444912001308	journal	March 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
Macromolecular structure determination using X-rays, neutrons and electrons: recent developments in Phenix Liebschner, Dorothee; Afonine, Pavel V.; Baker, Matthew L. Acta Crystallographica Section D Structural Biology, Vol. 75, Issue 10 https://doi.org/10.1107/s2059798319011471	journal	October 2019

Similar Records

N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum [alpha]-Glucosid

Journal Article · 2021 · J. Med. Chem. · OSTI ID:1845543

Karade, Sharanbasappa S.; Hill, Michelle L.; Kiappes, J.L.; +6 more

Discovery of 1H-Pyrazol-3(2H)-ones as Potent and Selective Inhibitors of Protein Kinase R-like Endoplasmic Reticulum Kinase (PERK)

Journal Article · 2015 · J. Med. Chem. · OSTI ID:1178824

Smith, Adrian L.; Andrews, Kristin L.; Beckmann, Holger; +20 more

Discovery of 7-Methyl-5-(1-{[3-(trifluoromethyl)phenyl]acetyl}-2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (GSK2606414), a Potent and Selective First-in-Class Inhibitor of Protein Kinase R (PKR)-like Endoplasmic Reticulum Kinase (PERK)

Journal Article · 2014 · Journal of Medicinal Chemistry · OSTI ID:1093478

Axten, Jeffrey M.; Medina, Jesús R.; Feng, Yanhong; +21 more

N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum ;#945;-Glucosida

Citation Formats

References (37)

Similar Records

Related Subjects