Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

Lin, L; Olson, M.; Sugane, T.; Turner, L.; Tararina, M.; Nielsen, A.; Kurbanov, E.; Pellett, S.; Johnson, E.; Cohen, S.; Allen, K.; Janda, K.

doi:10.1021/acs.jmedchem.0c01006

Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

Journal Article · 01 January 2022 · Journal of Medicinal Chemistry

DOI:https://doi.org/10.1021/acs.jmedchem.0c01006· OSTI ID:1690191

Lin, L; Olson, M.; Sugane, T.; Turner, L.; Tararina, M.; Nielsen, A.; Kurbanov, E.; Pellett, S.; Johnson, E.; Cohen, S.; Allen, K.; Janda, K.

Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Organization:: ~OTHER

DOE Contract Number:: SC0012704

OSTI ID:: 1690191

Report Number(s):: BNL-220512-2020-JACI

Journal Information:: Journal of Medicinal Chemistry, Vol. 63, Issue 19

Country of Publication:: United States

Language:: English

References (76)

Botulinum Toxin as a Biological Weapon: Medical and Public Health Management No authors listed JAMA https://doi.org/10.1001/jama.285.8.1059		February 2001
Recent developments in clinical trials of botulinum neurotoxins No authors listed Toxicon https://doi.org/10.1016/j.toxicon.2017.08.014		June 2018
Botulinum toxin in clinical practice No authors listed Journal of Neurology, Neurosurgery & Psychiatry https://doi.org/10.1136/jnnp.2003.034702		July 2004
Serious and Long-Term Adverse Events Associated with the Therapeutic and Cosmetic Use of Botulinum Toxin No authors listed Pharmacology https://doi.org/10.1159/000370245		January 2015
The Strange Case of the Botulinum Neurotoxin: Using Chemistry and Biology to Modulate the Most Deadly Poison No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.200705531		October 2008
The janus faces of botulinum neurotoxin: Sensational medicine and deadly biological weapon No authors listed Journal of Neuroscience Research https://doi.org/10.1002/jnr.21171		January 2007
Analyzing a bioterror attack on the food supply: The case of botulinum toxin in milk No authors listed Proceedings of the National Academy of Sciences https://doi.org/10.1073/pnas.0408526102		June 2005
Wound Botulism Associated With Black Tar Heroin Among Injecting Drug Users No authors listed JAMA https://doi.org/10.1001/jama.279.11.859		March 1998
Is black tar heroin use associated with wound botulism? A report of two Hispanic patients No authors listed Clinical Case Reports https://doi.org/10.1002/ccr3.1622		May 2018
Wound Botulism Outbreak Among Persons Who Use Black Tar Heroin — San Diego County, California, 2017–2018 No authors listed MMWR. Morbidity and Mortality Weekly Report https://doi.org/10.15585/mmwr.mm675152a3		January 2019
Translocation of botulinum neurotoxin light chain protease through the heavy chain channel No authors listed Nature Structural Biology https://doi.org/10.1038/nsb879		December 2002
Botulinum neurotoxin A selectively cleaves the synaptic protein SNAP-25 No authors listed Nature https://doi.org/10.1038/365160a0		September 1993
Tetanus and botulinum neurotoxins: mechanism of action and therapeutic uses No authors listed Philosophical Transactions of the Royal Society of London. Series B: Biological Sciences https://doi.org/10.1098/rstb.1999.0377		February 1999
Equine antitoxin use and other factors that predict outcome in type A foodborne botulism No authors listed The American Journal of Medicine https://doi.org/10.1016/0002-9343(84)90988-4		May 1984
The life history of a botulinum toxin molecule No authors listed Toxicon https://doi.org/10.1016/j.toxicon.2013.02.014		June 2013
The Light Chain Defines the Duration of Action of Botulinum Toxin Serotype A Subtypes No authors listed mBio https://doi.org/10.1128/mbio.00089-18		March 2018
Persistence of Botulinum Neurotoxin A Subtypes 1-5 in Primary Rat Spinal Cord Cells No authors listed PLoS ONE https://doi.org/10.1371/journal.pone.0090252		February 2014
Isolation and Characterization of the Novel Botulinum Neurotoxin A Subtype 6 No authors listed mSphere https://doi.org/10.1128/msphere.00466-18		October 2018
Strategies to Counteract Botulinum Neurotoxin A: Nature’s Deadliest Biomolecule No authors listed Accounts of Chemical Research https://doi.org/10.1021/acs.accounts.9b00261		July 2019
Targeting Metalloenzymes for Therapeutic Intervention No authors listed Chemical Reviews https://doi.org/10.1021/acs.chemrev.8b00201		September 2018
Identification of a Potent Botulinum Neurotoxin A Protease Inhibitor Using in Situ Lead Identification Chemistry No authors listed Organic Letters https://doi.org/10.1021/ol0603211		April 2006
Synthesis and structure–activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors No authors listed Bioorganic & Medicinal Chemistry Letters https://doi.org/10.1016/j.bmcl.2007.09.103		December 2007
Chirality Holds the Key for Potent Inhibition of the Botulinum Neurotoxin Serotype A Protease No authors listed Organic Letters https://doi.org/10.1021/ol902820z		January 2010
Synthesis/biological evaluation of hydroxamic acids and their prodrugs as inhibitors for Botulinum neurotoxin A light chain No authors listed Bioorganic & Medicinal Chemistry https://doi.org/10.1016/j.bmc.2013.11.053		February 2014
Structures of Clostridium botulinum Neurotoxin Serotype A Light Chain Complexed with Small-Molecule Inhibitors Highlight Active-Site Flexibility No authors listed Chemistry & Biology https://doi.org/10.1016/j.chembiol.2007.03.014		May 2007
Evaluation of adamantane hydroxamates as botulinum neurotoxin inhibitors: Synthesis, crystallography, modeling, kinetic and cellular based studies No authors listed Bioorganic & Medicinal Chemistry https://doi.org/10.1016/j.bmc.2012.12.001		March 2013
Identification of a botulinum neurotoxin A protease inhibitor displaying efficacy in a cellular model No authors listed Chemical Communications https://doi.org/10.1039/b603099h		January 2006
Effects of hydroxamate metalloendoprotease inhibitors on botulinum neurotoxin A poisoned mouse neuromuscular junctions No authors listed Neuropharmacology https://doi.org/10.1016/j.neuropharm.2010.02.014		June 2010
Reexamining hydroxamate inhibitors of botulinum neurotoxin serotype A: Extending towards the β-exosite No authors listed Bioorganic & Medicinal Chemistry Letters https://doi.org/10.1016/j.bmcl.2012.04.019		June 2012
Mechanism-based Inhibition of Metalloproteinases No authors listed Frontiers in Medicinal Chemistry - Online https://doi.org/10.2174/1567204043396325		January 2004
Benzylidene cyclopentenediones: First irreversible inhibitors against botulinum neurotoxin A’s zinc endopeptidase No authors listed Bioorganic & Medicinal Chemistry Letters https://doi.org/10.1016/j.bmcl.2009.10.129		January 2010
Novel benzimidazole inhibitors of botulinum neurotoxin/A display enzyme and cell-based potency No authors listed The Botulinum J. https://doi.org/10.1504/tbj.2011.041813		January 2011
Time-dependent botulinum neurotoxin serotype A metalloprotease inhibitors No authors listed Bioorganic & Medicinal Chemistry https://doi.org/10.1016/j.bmc.2011.10.062		December 2011
Benzoquinones as inhibitors of botulinum neurotoxin serotype A No authors listed Bioorganic & Medicinal Chemistry https://doi.org/10.1016/j.bmc.2014.06.004		August 2014
Covalent Modifiers of Botulinum Neurotoxin Counteract Toxin Persistence No authors listed ACS Chemical Biology https://doi.org/10.1021/acschembio.8b00937		December 2018
High-Throughput Multiplex Flow Cytometry Screening for Botulinum Neurotoxin Type A Light Chain Protease Inhibitors No authors listed ASSAY and Drug Development Technologies https://doi.org/10.1089/adt.2009.0219		February 2010
Ebselen, a useful tool for understanding cellular redox biology and a promising drug candidate for use in human diseases No authors listed Archives of Biochemistry and Biophysics https://doi.org/10.1016/j.abb.2015.10.024		April 2016
Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors No authors listed Nature https://doi.org/10.1038/s41586-020-2223-y		April 2020
Structural Analysis of Botulinum Neurotoxin Type E Catalytic Domain and Its Mutant Glu212→Gln Reveals the Pivotal Role of the Glu212 Carboxylate in the Catalytic Pathway ^† ^, ^‡ No authors listed Biochemistry https://doi.org/10.1021/bi036278w		June 2004
Structural Analysis of Botulinum Neurotoxin Serotype F Light Chain: Implications on Substrate Binding and Inhibitor Design No authors listed Biochemistry https://doi.org/10.1021/bi0510072		August 2005
Structural and Biochemical Studies of Botulinum Neurotoxin Serotype C1 Light Chain Protease: Implications for Dual Substrate Specificity ^, No authors listed Biochemistry https://doi.org/10.1021/bi701162d		August 2007
Crystal Structure of Botulinum Neurotoxin Type G Light Chain: Serotype Divergence in Substrate Recognition ^, No authors listed Biochemistry https://doi.org/10.1021/bi0505924		June 2005
Structural characterisation of the catalytic domain of botulinum neurotoxin X - high activity and unique substrate specificity No authors listed Scientific Reports https://doi.org/10.1038/s41598-018-22842-4		March 2018
Structure of Botulinum Neurotoxin Type D Light Chain at 1.65 Å Resolution: Repercussions for VAMP-2 Substrate Specificity ^, No authors listed Biochemistry https://doi.org/10.1021/bi052518r		February 2006
Identification of Clinically Viable Quinolinol Inhibitors of Botulinum Neurotoxin A Light Chain No authors listed Journal of Medicinal Chemistry https://doi.org/10.1021/jm4012164		January 2014
Quinolinol and peptide inhibitors of zinc protease in botulinum neurotoxin A: Effects of zinc ion and peptides on inhibition No authors listed Archives of Biochemistry and Biophysics https://doi.org/10.1016/j.abb.2009.09.008		November 2009
Efficacy of certain quinolines as pharmacological antagonists in botulinum neurotoxin poisoning No authors listed Toxicon https://doi.org/10.1016/s0041-0101(96)00147-x		March 1997
Newly Designed Quinolinol Inhibitors Mitigate the Effects of Botulinum Neurotoxin A in Enzymatic, Cell-Based, and ex Vivo Assays No authors listed Journal of Medicinal Chemistry https://doi.org/10.1021/acs.jmedchem.6b01393		January 2017
New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model No authors listed Journal of Medicinal Chemistry https://doi.org/10.1021/acs.jmedchem.7b01710		February 2018
Toward the discovery of potent inhibitors of botulinum neurotoxin A: development of a robust LC MS based assay operational from low to subnanomolar enzyme concentrations No authors listed Chemical Communications https://doi.org/10.1039/b808305c		January 2008
Aryl Vinyl Sulfonates and Sulfones as Active Site-Directed and Mechanism-Based Probes for Protein Tyrosine Phosphatases No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja711125p		June 2008
Comparison of methods for analyzing kinetic data from mechanism-based enzyme inactivation: Application to nitric oxide synthase No authors listed AAPS PharmSci https://doi.org/10.1208/ps020108		March 2000
The Alkyne Moiety as a Latent Electrophile in Irreversible Covalent Small Molecule Inhibitors of Cathepsin K No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b11027		January 2019
A comparative study of warheads for design of cysteine protease inhibitors No authors listed Bioorganic & Medicinal Chemistry Letters https://doi.org/10.1016/j.bmcl.2017.10.002		November 2017
Development of a Fluorescence Internal Quenching Correction Factor to Correct Botulinum Neurotoxin Type A Endopeptidase Kinetics Using SNAPtide No authors listed Analytical Chemistry https://doi.org/10.1021/ac302997n		December 2012
Synthesis, Characterization and Development of a High-Throughput Methodology for the Discovery of Botulinum Neurotoxin A Inhibitors No authors listed Journal of Combinatorial Chemistry https://doi.org/10.1021/cc060010h		May 2006
An in vitro and in vivo disconnect uncovered through high-throughput identification of botulinum neurotoxin A antagonists No authors listed Proceedings of the National Academy of Sciences https://doi.org/10.1073/pnas.0611213104		February 2007
Antitoxin Levels in Botulism Patients Treated with Trivalent Equine Botulism Antitoxin to Toxin Types A, B, and E No authors listed Journal of Infectious Diseases https://doi.org/10.1093/infdis/150.3.407		September 1984
Docking Covalent Inhibitors: A Parameter Free Approach To Pose Prediction and Scoring No authors listed Journal of Chemical Information and Modeling https://doi.org/10.1021/ci500118s		June 2014
Matrix metalloproteinase inhibitors as therapy for inflammatory and vascular diseases No authors listed Nature Reviews Drug Discovery https://doi.org/10.1038/nrd2308		June 2007
To bind zinc or not to bind zinc: An examination of innovative approaches to improved metalloproteinase inhibition No authors listed Biochimica et Biophysica Acta (BBA) - Molecular Cell Research https://doi.org/10.1016/j.bbamcr.2009.08.006		January 2010
Zinc-Binding Groups Modulate Selective Inhibition of MMPs No authors listed ChemMedChem https://doi.org/10.1002/cmdc.200700290		May 2008
Metal Ions Effectively Ablate the Action of Botulinum Neurotoxin A No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.7b01084		May 2017
The C-terminus of botulinum neurotoxin type A light chain contributes to solubility, catalysis, and stability No authors listed Protein Expression and Purification https://doi.org/10.1016/j.pep.2004.05.009		September 2004
Catalytic Features of the Botulinum Neurotoxin A Light Chain Revealed by High Resolution Structure of an Inhibitory Peptide Complex ^† ^‡ No authors listed Biochemistry https://doi.org/10.1021/bi8001067		May 2008
[20] Processing of X-ray diffraction data collected in oscillation mode No authors listed Macromolecular Crystallography Part A https://doi.org/10.1016/s0076-6879(97)76066-x		January 1997
Phaser crystallographic software No authors listed Journal of Applied Crystallography https://doi.org/10.1107/s0021889807021206		July 2007
Iterative model building, structure refinement and density modification with the PHENIX AutoBuild wizard No authors listed Acta Crystallographica Section D Biological Crystallography https://doi.org/10.1107/s090744490705024x		December 2007
Coot model-building tools for molecular graphics No authors listed Acta Crystallographica Section D Biological Crystallography https://doi.org/10.1107/s0907444904019158		November 2004
Polder maps: improving OMIT maps by excluding bulk solvent No authors listed Acta Crystallographica Section D Structural Biology https://doi.org/10.1107/s2059798316018210		February 2017
OPLS3: A Force Field Providing Broad Coverage of Drug-like Small Molecules and Proteins No authors listed Journal of Chemical Theory and Computation https://doi.org/10.1021/acs.jctc.5b00864		December 2015
The Protein Data Bank No authors listed Nucleic Acids Research https://doi.org/10.1093/nar/28.1.235		January 2000
Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments No authors listed Journal of Computer-Aided Molecular Design https://doi.org/10.1007/s10822-013-9644-8		March 2013
A neuronal cell-based botulinum neurotoxin assay for highly sensitive and specific detection of neutralizing serum antibodies No authors listed FEBS Letters https://doi.org/10.1016/j.febslet.2007.08.078		September 2007
Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays No authors listed Journal of Immunological Methods https://doi.org/10.1016/0022-1759(83)90303-4		December 1983
An Aggregation Advisor for Ligand Discovery No authors listed Journal of Medicinal Chemistry https://doi.org/10.1021/acs.jmedchem.5b01105		August 2015

Similar Records

Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

Journal Article · 2020 · J. Med. Chem. · OSTI ID:1682323

Lin, Lucy; Olson, Margaret E.; Sugane, Takashi; +9 more

Advances in Assays and Analytical Approaches for Botulinum Toxin Detection

Journal Article · 2010 · Trends in Analytical Chemistry. TrAC, 29(10):1137-1156 · OSTI ID:991572

Grate, Jay W; Ozanich, Richard M; Warner, Marvin G; +2 more

TOXIN PRODUCTION BY CLOSTRIDIUM BOTULINUM, TYPE E, IN VACUUM-PACKED, IRRADIATED FRESH FISH IN RELATION TO CHANGES OF THE ASSOCIATED MICROFLORA

Journal Article · 1965 · Canadian Journal of Microbiology (Canada) · OSTI ID:4620894

Abrahamsson, K; DeSilva, N N; Molin, N

Related Subjects

99 GENERAL AND MISCELLANEOUS

Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

Citation Formats

References (76)

Similar Records

Related Subjects