4.7 Review

Reactive chemistry for covalent probe and therapeutic development

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Review Pharmacology & Pharmacy

Targeting Endocannabinoid Signaling: FAAH and MAG Lipase Inhibitors

Noelle van Egmond et al.

Summary: Researchers have developed compounds to modulate the endocannabinoid system in the human brain, including inhibitors of FAAH and MAGL to exert therapeutic effects without inducing adverse reactions associated with direct stimulation of the CB1 receptor by THC. These compounds have potential for treatment without the side effects of THC.

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, VOL 61, 2021 (2021)

Article Biotechnology & Applied Microbiology

Reimagining high-throughput profiling of reactive cysteines for cell-based screening of large electrophile libraries

Miljan Kuljanin et al.

Summary: This study presents a redesigned workflow called streamlined cysteine activity-based protein profiling (SLC-ABPP) for measuring amino acid side-chain reactivity, which significantly improves sample throughput. The method has been successfully applied to identify proteome-wide targets of various covalent inhibitors, while also creating a resource of cysteine reactivity data for further research.

NATURE BIOTECHNOLOGY (2021)

Article Biochemistry & Molecular Biology

Discovery of a Cell-Active SuTEx Ligand of Prostaglandin Reductase 2

Emmanuel K. Toroitich et al.

Summary: The study demonstrated the potential of SuTEx compounds in covalent modification of protein tyrosine sites and identified HHS-0701 as a cell-active inhibitor targeting prostaglandin reductase 2.

CHEMBIOCHEM (2021)

Article Chemistry, Multidisciplinary

Tunable Methacrylamides for Covalent Ligand Directed Release Chemistry

Rambabu N. Reddi et al.

Summary: This study introduces a new class of alpha-substituted methacrylamides as potential electrophiles for targeted covalent inhibitors, showing higher thiol reactivity and undergoing a conjugated addition-elimination reaction. These electrophiles demonstrated comparable potency and improved selectivity in various assays, making them a versatile addition to the toolbox of targeted covalent inhibitor design.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Functionalized Scout Fragments for Site-Specific Covalent Ligand Discovery and Optimization

Vincent M. Crowley et al.

Summary: Covalent ligands are versatile chemical probes and drugs that target noncanonical sites on proteins, but further optimization is needed to overcome technical challenges. Broadly reactive electrophilic fragments can be converted into site-specific target engagement probes, providing a roadmap to optimize covalent fragments into more advanced chemical probes.

ACS CENTRAL SCIENCE (2021)

Article Chemistry, Analytical

Direct Target Site Identification of a Sulfonyl-Triazole Covalent Kinase Probe by LC-MS Chemical Proteomics

Rebecca L. McCloud et al.

Summary: Chemical proteomics is a widely used method for investigating protein activity and small molecule ligand binding. LC-MS/MS is employed to assess covalent probe binding and inhibition, providing molecular information on targeted proteins and probe-modified sites. Key bioanalytical conditions have been revealed to guide future direct target site identification of complex irreversible probes and inhibitors.

ANALYTICAL CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

A Genetically Encoded Fluorosulfonyloxybenzoyl-L-lysine for Expansive Covalent Bonding of Proteins via SuFEx Chemistry

Jun Liu et al.

Summary: Introducing novel chemical bonds into proteins offers innovative possibilities, with the incorporation of latent bioreactive unnatural amino acids providing a powerful system for covalent targeting of natural residues. This approach has potential applications in biochemical research and protein engineering.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Site-selective tyrosine bioconjugation via photoredox catalysis for native-to-bioorthogonal protein transformation

Beryl X. Li et al.

Summary: This study presents a novel method for site-selective tyrosine bioconjugation using photoredox catalysis, which allows for chemically modifying native proteins with high site-selectivity. The water-soluble photocatalyst lumiflavin has been demonstrated to induce oxidative coupling between a phenoxazine dialdehyde tag and a single tyrosine site on native proteins, even in the presence of multiple tyrosyl side chains, enabling the synthesis of structurally defined fluorescent conjugates.

NATURE CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

SuFExable polymers with helical structures derived from thionyl tetrafluoride

Suhua Li et al.

Summary: SuFEx is a type of click chemistry that allows covalent linking of modular units through sulfur(vi) connective hubs, leading to the synthesis of structurally diverse copolymers with high efficiency and stable bonds. SuFEx click chemistry offers the potential for post-polymerization modification, enabling the synthesis of materials with control over composition and conformation, making it a powerful tool in polymer chemistry.

NATURE CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

A proteome-wide atlas of lysine-reactive chemistry

Mikail E. Abbasov et al.

Summary: Recent advances in chemical proteomics have identified and characterized a wide range of uncharted aminophilic chemotypes that greatly expand the ligandable lysines in human proteins. Aminophilic electrophiles showed varying proteomic reactivities, from selective interactions with specific lysines to broad engagement with covalent small-molecule-lysine interactions. The study demonstrates the potential of covalent chemistry in targeting functional lysines in the human proteome, perturbing diverse biochemical functions.

NATURE CHEMISTRY (2021)

Review Biochemistry & Molecular Biology

Development and biological applications of sulfur-triazole exchange (SuTEx) chemistry

Adam L. Borne et al.

Summary: This review article discusses the development of sulfonyl-triazoles as a new class of electrophiles for sulfur-triazole exchange chemistry, allowing for the modification of protein residues and providing additional capabilities for tuning the sulfur electrophile. Modifications to the leaving group and adduct group can facilitate nucleophilic substitution reactions in live cells, making SuTEx an efficient platform for developing chemical probes with tunable bioactivity.

RSC CHEMICAL BIOLOGY (2021)

Article Chemistry, Multidisciplinary

Chemoproteomic profiling of kinases in live cells using electrophilic sulfonyl triazole probes

Tao Huang et al.

Summary: The sulfonyl-triazoles (SuTEx) chemistry is a new type of electrophile that can react covalently with proteins, useful for chemical proteomics and protein ligand discovery. Functionalized SuTEx probes have been utilized to map protein interaction networks and discover binding sites in live cells, leading to the identification of important probe-modified sites within the protein kinase C-alpha C2 domain.

CHEMICAL SCIENCE (2021)

Review Biochemistry & Molecular Biology

Fragment-based covalent ligand discovery

Wenchao Lu et al.

Summary: Targeted covalent inhibitors have become a focus in drug discovery, with chemoproteomic strategies and fragment-based drug discovery leading to the identification of new drugs and protein targets. This approach enables high-throughput discovery of potential protein targets and allows for targeting of various amino acids using new chemical technologies.

RSC CHEMICAL BIOLOGY (2021)

Article Biochemistry & Molecular Biology

Global targeting of functional tyrosines using sulfur-triazole exchange chemistry

Heung Sik Hahm et al.

NATURE CHEMICAL BIOLOGY (2020)

Review Biochemistry & Molecular Biology

A global analysis of function and conservation of catalytic residues in enzymes

Antonio J. M. Ribeiro et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2020)

Review Chemistry, Organic

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Yan-Ping Meng et al.

SYNTHESIS-STUTTGART (2020)

Article Chemistry, Multidisciplinary

2H-Azirine-Based Reagents for Chemoselective Bioconjugation at Carboxyl Residues Inside Live Cells

Nan Ma et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Liganding Functional Tyrosine Sites on Proteins Using Sulfur- Triazole Exchange Chemistry

Jeffrey W. Brulet et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Biochemistry & Molecular Biology

Selective covalent targeting of GPX4 using masked nitrile-oxide electrophiles

John K. Eaton et al.

NATURE CHEMICAL BIOLOGY (2020)

Article Chemistry, Multidisciplinary

A General Approach toO-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction

Chao Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Tyrosine Conjugation Methods for Protein Labelling

Dimitri Alvarez Dorta et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Biochemistry & Molecular Biology

Developing Covalent Protein Drugs via Proximity-Enabled Reactive Therapeutics

Qingke Li et al.

Article Biochemistry & Molecular Biology

An Activity-Guided Map of Electrophile-Cysteine Interactions in Primary Human T Cells

Ekaterina V. Vinogradova et al.

Article Chemistry, Multidisciplinary

Using sulfuramidimidoyl fluorides that undergo sulfur(vi) fluoride exchange for inverse drug discovery

Gabriel J. Brighty et al.

NATURE CHEMISTRY (2020)

Review Chemistry, Organic

Tyrosine bioconjugation - an emergent alternative

Peter A. Szijj et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Review Biochemistry & Molecular Biology

Structure-based design and analysis of SuFEx chemical probes

Lyn H. Jones et al.

RSC MEDICINAL CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

On the scope of SuFEx as a bioorthogonal click process

Alberto Marra et al.

NEW JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Fluorescent Triazole Urea Activity-Based Probes for the Single-Cell Phenotypic Characterization of Staphylococcus aureus

Linhai Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Biochemistry & Molecular Biology

N-Acyl pyrazoles: Effective and tunable inhibitors of serine hydrolases

Katerina Otrubova et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2019)

Review Chemistry, Medicinal

Covalent Inhibition in Drug Discovery

Avick Kumar Ghosh et al.

CHEMMEDCHEM (2019)

Review Biochemistry & Molecular Biology

Lysine-Targeted Inhibitors and Chemoproteomic Probes

Adolfo Cuesta et al.

ANNUAL REVIEW OF BIOCHEMISTRY, VOL 88 (2019)

Review Chemistry, Multidisciplinary

Chemical Biology Approaches to Interrogate the Selenoproteome

Jennifer C. Peeler et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Article Multidisciplinary Sciences

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Qinheng Zheng et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2019)

Review Chemistry, Medicinal

Boron in drug design: Recent advances in the development of new therapeutic agents

Guilherme Felipe Santos Fernandes et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Multidisciplinary Sciences

The clinical KRAS(G12C) inhibitor AMG 510 drives anti-tumour immunity

Jude Canon et al.

NATURE (2019)

Review Chemistry, Multidisciplinary

The growing applications of SuFEx click chemistry

A. S. Barrow et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Inverse Drug Discovery Strategy To Identify Proteins That Are Targeted by Latent Electrophiles As Exemplified by Aryl Fluorosulfates

David E. Mortenson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Chemistry, Multidisciplinary

The Cysteinome of Protein Kinases as a Target in Drug Development

Apirat Chaikuad et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Biochemistry & Molecular Biology

Targeting KRAS Mutant Cancers with a Covalent G12C-Specific Inhibitor

Matthew R. Janes et al.

Review Chemistry, Multidisciplinary

Structure-based design of targeted covalent inhibitors

Richard Lonsdale et al.

CHEMICAL SOCIETY REVIEWS (2018)

Review Pharmacology & Pharmacy

Progress with covalent small-molecule kinase inhibitors

Zheng Zhao et al.

DRUG DISCOVERY TODAY (2018)

Article Chemistry, Medicinal

Novel K-Ras G12C Switch-II Covalent Binders Destabilize Ras and Accelerate Nucleotide Exchange

Chimno I. Nnadi et al.

JOURNAL OF CHEMICAL INFORMATION AND MODELING (2018)

Article Chemistry, Multidisciplinary

SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization

Zilei Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Biotechnology & Applied Microbiology

Unexplored therapeutic opportunities in the human genome

Tudor I. Oprea et al.

NATURE REVIEWS DRUG DISCOVERY (2018)

Article Chemistry, Multidisciplinary

Selenium-Encoded Isotopic Signature Targeted Profiling

Jinjun Gao et al.

ACS CENTRAL SCIENCE (2018)

Article Chemistry, Multidisciplinary

Sub-picomolar Inhibition of HIV-1 Protease with a Boronic Acid

Ian W. Windsor et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Biochemical Research Methods

A Perspective on the Kinetics of Covalent and Irreversible Inhibition

John M. Strelow

SLAS DISCOVERY (2017)

Article Chemistry, Multidisciplinary

Broad-Spectrum Kinase Profiling in Live Cells with Lysine-Targeted Sulfonyl Fluoride Probes

Qian Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Global profiling of lysine reactivity and ligandability in the human proteome

Stephan M. Hacker et al.

NATURE CHEMISTRY (2017)

Article Multidisciplinary Sciences

Redox-based reagents for chemoselective methionine bioconjugation

Shixian Lin et al.

SCIENCE (2017)

Article Biochemistry & Molecular Biology

Proteome-wide Map of Targets of T790M-EGFR-Directed Covalent Inhibitors

Sherry Niessen et al.

CELL CHEMICAL BIOLOGY (2017)

Article Biochemistry & Molecular Biology

Regulation of calcium release from the endoplasmic reticulum by the serine hydrolase ABHD2

Bogeon Yun et al.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2017)

Article Biochemistry & Molecular Biology

Covalent Enzyme Inhibition through Fluorosulfate Modification of a Noncatalytic Serine Residue

Olugbeminiyi O. Fadeyi et al.

ACS CHEMICAL BIOLOGY (2017)

Article Biochemistry & Molecular Biology

NHS-Esters As Versatile Reactivity-Based Probes for Mapping Proteome-Wide Ligandable Hotspots

Carl C. Ward et al.

ACS CHEMICAL BIOLOGY (2017)

Article Multidisciplinary Sciences

Rapid and profound rewiring of brain lipid signaling networks by acute diacylglycerol lipase inhibition

Daisuke Ogasawara et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2016)

Article Chemistry, Multidisciplinary

Metabolically Labile Fumarate Esters Impart Kinetic Selectivity to Irreversible Inhibitors

Balyn W. Zaro et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Multidisciplinary Sciences

Proteome-wide covalent ligand discovery in native biological systems

Keriann M. Backus et al.

NATURE (2016)

Article Biochemistry & Molecular Biology

Inhibition of Mcl-1 through covalent modification of a noncatalytic lysine side chain

Gizem Akcay et al.

NATURE CHEMICAL BIOLOGY (2016)

Article Multidisciplinary Sciences

Allele-specific inhibitors inactivate mutant KRAS G12C by a trapping mechanism

Piro Lito et al.

SCIENCE (2016)

Article Biochemistry & Molecular Biology

Rational Targeting of Active-Site Tyrosine Residues Using Sulfonyl Fluoride Probes

Erik C. Hett et al.

ACS CHEMICAL BIOLOGY (2015)

Article Biochemistry & Molecular Biology

The influence of fluorine position on the properties of fluorobenzoxaboroles

Agnieszka Adamczyk-Wozniak et al.

BIOORGANIC CHEMISTRY (2015)

Review Chemistry, Multidisciplinary

Recent Developments in the Chemistry and Biological Applications of Benzoxaboroles

Agnieszka Adamczyk-Wozniak et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Medicinal

Discovery of a Cyclic Boronic Acid β-Lactamase Inhibitor (RPX7009) with Utility vs Class A Serine Carbapenemases

Scott J. Hecker et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Review Otorhinolaryngology

Ubiquitous Aspirin: A Systematic Review of Its Impact on Sensorineural Hearing Loss

Meghann Elizabeth Kyle et al.

OTOLARYNGOLOGY-HEAD AND NECK SURGERY (2015)

Review Chemistry, Multidisciplinary

Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry

Jiajia Dong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Review Biochemistry & Molecular Biology

Enzyme Inhibitor Discovery by Activity-Based Protein Profiling

Micah J. Niphakis et al.

ANNUAL REVIEW OF BIOCHEMISTRY, VOL 83 (2014)

Review Biochemistry & Molecular Biology

Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

Craig S. McKay et al.

CHEMISTRY & BIOLOGY (2014)

Review Biochemistry & Molecular Biology

Understanding and applying tyrosine biochemical diversity

Lyn H. Jones et al.

MOLECULAR BIOSYSTEMS (2014)

Article Biochemistry & Molecular Biology

A road map to evaluate the proteome-wide selectivity of covalent kinase inhibitors

Bryan R. Lannine et al.

NATURE CHEMICAL BIOLOGY (2014)

Article Cell Biology

The Genesis of Tyrosine Phosphorylation

Tony Hunter

COLD SPRING HARBOR PERSPECTIVES IN BIOLOGY (2014)

Article Biochemistry & Molecular Biology

Evaluation of NHS Carbamates as a Potent and Selective Class of Endocannabinoid Hydrolase Inhibitors

Micah J. Niphakis et al.

ACS CHEMICAL NEUROSCIENCE (2013)

Review Biochemistry & Molecular Biology

Developing Irreversible Inhibitors of the Protein Kinase Cysteinome

Qingsong Liu et al.

CHEMISTRY & BIOLOGY (2013)

Article Biochemistry & Molecular Biology

Characterization of a Serine Hydrolase Targeted by Acyl-protein Thioesterase Inhibitors in Toxoplasma gondii

Louise E. Kemp et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

An Alkyne-Aspirin Chemical Reporter for the Detection of Aspirin-Dependent Protein Modification in Living Cells

Leslie A. Bateman et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Multidisciplinary Sciences

K-Ras(G12C) inhibitors allosterically control GTP affinity and effector interactions

Jonathan M. Ostrem et al.

NATURE (2013)

Review Pharmacology & Pharmacy

Chemical Probes of Endocannabinoid Metabolism

Jacqueline L. Blankman et al.

PHARMACOLOGICAL REVIEWS (2013)

Review Chemistry, Multidisciplinary

Boron Containing Compounds as Protease Inhibitors

Reem Smoum et al.

CHEMICAL REVIEWS (2012)

Review Pharmacology & Pharmacy

Drug discovery for a new generation of covalent drugs

Amit S. Kalgutkar et al.

EXPERT OPINION ON DRUG DISCOVERY (2012)

Review Biotechnology & Applied Microbiology

The pharmacological landscape and therapeutic potential of serine hydrolases

Daniel A. Bachovchin et al.

NATURE REVIEWS DRUG DISCOVERY (2012)

Article Chemistry, Medicinal

Ring Structure and Aromatic Substituent Effects on the pKa of the Benzoxaborole Pharmacophore

John W. Tomsho et al.

ACS MEDICINAL CHEMISTRY LETTERS (2012)

Review Chemistry, Multidisciplinary

The Metabolic Serine Hydrolases and Their Functions in Mammalian Physiology and Disease

Jonathan Z. Long et al.

CHEMICAL REVIEWS (2011)

Article Biochemistry & Molecular Biology

Click-generated triazole ureas as ultrapotent in vivo-active serine hydrolase inhibitors

Alexander Adibekian et al.

NATURE CHEMICAL BIOLOGY (2011)

Review Biotechnology & Applied Microbiology

The resurgence of covalent drugs

Juswinder Singh et al.

NATURE REVIEWS DRUG DISCOVERY (2011)

Article Chemistry, Medicinal

Strategies for discovering and derisking covalent, irreversible enzyme inhibitors

Douglas S. Johnson et al.

FUTURE MEDICINAL CHEMISTRY (2010)

Review Biochemistry & Molecular Biology

Activity-based Proteomics of Enzyme Superfamilies: Serine Hydrolases as a Case Study

Gabriel M. Simon et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2010)

Article Multidisciplinary Sciences

The Bruton tyrosine kinase inhibitor PCI-32765 blocks B-cell activation and is efficacious in models of autoimmune disease and B-cell malignancy

Lee A. Honigberg et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2010)

Article Biochemistry & Molecular Biology

Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects

Jonathan Z. Long et al.

NATURE CHEMICAL BIOLOGY (2009)

Article Biochemistry & Molecular Biology

Crystal structure of the thioesterase domain of human fatty acid synthase inhibited by Orlistat

Charles W. Pemble et al.

NATURE STRUCTURAL & MOLECULAR BIOLOGY (2007)

Article Biochemistry & Molecular Biology

Activity-based probes that target diverse cysteine protease families

D Kato et al.

NATURE CHEMICAL BIOLOGY (2005)

Article Biotechnology & Applied Microbiology

Biochemical mechanisms of drug action: what does it take for success?

DC Swinney

NATURE REVIEWS DRUG DISCOVERY (2004)