Metal-promoted synthetic chemistry within living cells

Article Chemistry, Medicinal

Dual-Bioorthogonal Catalysis by a Palladium Peptide Complex

Ana M. Perez-Lopez et al.

Summary: Artificial metalloenzymes (ArMs) enhance bioorthogonal chemistry by introducing new reactions and minimizing metal deactivation and toxicity, enabling the activation of therapeutics in vivo.

JOURNAL OF MEDICINAL CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Assembly and Evolution of Artificial Metalloenzymes within E. coli Nissle 1917 for Enantioselective and Site-Selective Functionalization of C-H and C=C Bonds

Zhennan Liu et al.

Summary: The potential applications of artificial metalloenzymes (ArMs) in microorganisms are significant. In this study, the non-pathogenic E. coli strain Nissle 1917 (EcN) was used as a host to create ArMs from cytochrome P450s and artificial heme cofactors. The transport of an iridium porphyrin into the cell was facilitated by an outer-membrane receptor in EcN. The Ir-CYP119 assembled in vivo catalyzed carbene insertions into benzylic C-H bonds with enantioselectivity and site-selectivity. Using EcN as a whole-cell screening platform improved efficiency, simplified procedures, and accelerated the development of Ir-CYP119 with enhanced catalytic properties.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Multidisciplinary Sciences

Synthetic prodrug design enables biocatalytic activation in mice to elicit tumor growth suppression

Igor Nasibullin et al.

Nature Communications (2022)

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Article Chemistry, Multidisciplinary

A general strategy for in situ assembly of light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling

Xiang Li et al.

Summary: This study presents a general strategy for the in situ assembly of intramolecular charge-transfer (ICT)-based light up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling reaction. The designed fluorophores showed significant fluorescence enhancement and high fluorescence quantum yield after reaction with aryl boronic acid or boronate. They have been successfully applied in peptide conjugation, no-wash fluorogenic protein labeling, and mitochondria-selective bioorthogonal imaging in live cells.

CHINESE CHEMICAL LETTERS (2022)

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Article Multidisciplinary Sciences

DNA-based platform for efficient and precisely targeted bioorthogonal catalysis in living systems

Yawen You et al.

Summary: This study reports on a DNA-based biocompatible, highly efficient, and precisely targeted copper nanocatalyst, which exhibits excellent catalytic activity and achieves efficient prodrug activation and antitumor effects in cancer cells.

NATURE COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

In Vivo Olefin Metathesis in Microalgae Upgrades Lipids to Building Blocks for Polymers and Chemicals

Natalie S. Schunck et al.

Summary: Sustainable sources are crucial for chemicals production, and microalgae have the potential to catalytically convert renewable substrates inside living cells, generating valuable building blocks for chemical production.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

NIR-II Light Leveraged Dual Drug Synthesis for Orthotopic Combination Therapy

Huisi Zhao et al.

Summary: In this study, a NIR-II light promoted integrated catalyst is designed to accelerate the reaction efficiency and achieve a dual bioorthogonal reaction for combination therapy. The results show that this integrated catalyst exhibits significant anti-tumor activity in vivo.

ACS NANO (2022)

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Review Chemistry, Multidisciplinary

Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes

Sara Gutierrez et al.

Summary: Translating the power of transition metal catalysis to the native habitats of enzymes can expand the possibilities of studying and manipulating biological systems. Recent research has demonstrated the feasibility of performing metal carbene chemistry in aqueous and biorelevant media.

CHEMICAL SCIENCE (2022)

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Review Chemistry, Multidisciplinary

Bioorthogonal catalysis for biomedical applications

Tingxizi Liang et al.

Summary: Bioorthogonal chemistry has made substantial progress in the past few decades and has been widely applied in biomedical practices. This article reviews the development and recent advances of bioorthogonal chemistry, with a focus on the biomedical application of bioorthogonal catalysis.

TRENDS IN CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

Transition Metal-Promoted Reactions in Aqueous Media and Biological Settings

Paolo Destito et al.

Summary: Developing non-natural biocompatible transformations in biologically relevant media has attracted significant interest in the past decade, with the use of transition metal complexes offering unique possibilities. This translation of metal catalyst potential to biological environments poses challenges, but describing the most relevant advances and key challenges helps identify issues from an organometallic perspective.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Plasmonic-Assisted Thermocyclizations in Living Cells Using Metal-Organic Framework Based Nanoreactors

Carolina Carrillo-Carrion et al.

Summary: A microporous plasmonic nanoreactor was designed for intracellular photothermal-driven reactions, allowing efficient diffusion of reactants into the plasmonic chamber in living cells. The core-shell structure consists of a gold nanostar core embedded within a metal-organic framework, enabling the generation of cyclic fluorescent products within the cells, which can be tracked using fluorescence microscopy.

ACS NANO (2021)

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Article Chemistry, Multidisciplinary

Bioorthogonal Activation of Dual Catalytic and Anti-Cancer Activities of Organogold(I) Complexes in Living Systems

Yan Long et al.

Summary: A new bioorthogonal activation approach utilizing Pd(II)-triggered transmetallation reactions has been reported to conditionally activate the bio-reactivity of NHC-Au(I)-phenylacetylide complexes. This activation approach shows potential applications in inhibiting cancer cell proliferation and angiogenesis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

In Vivo Assembly of Artificial Metalloenzymes and Application in Whole-Cell Biocatalysis**

Shreyans Chordia et al.

Summary: The study demonstrates the supramolecular assembly of ArMs in E. coli cells and their application in enzyme catalysis. Improved mutants were obtained through directed evolution, and the whole-cell ArM system showed catalytic activity without the need for engineering.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Unnatural biosynthesis by an engineered microorganism with heterologously expressed natural enzymes and an artificial metalloenzyme

Jing Huang et al.

Summary: Synthetic biology combines natural and artificial enzymes in engineered microbial cells to produce highly selective unnatural products, expanding the research field of biosynthesis.

NATURE CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Prodrug Activation by Gold Artificial Metalloenzyme-Catalyzed Synthesis of Phenanthridinium Derivatives via Hydroamination

Tsung-Che Chang et al.

Summary: A novel approach in targeted drug delivery involves using abiotic metal-triggered prodrug mechanisms, particularly through gold-catalyzed activation under physiological conditions. The use of a gold artificial metalloenzyme based on human serum albumin for prodrug activation enhances biocompatibility and therapeutic efficacy, showing potential for anticancer applications.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

A Bimetallic Metal-Organic Framework Encapsulated with DNAzyme for Intracellular Drug Synthesis and Self-Sufficient Gene Therapy

Zhao Wang et al.

Summary: A novel treatment method has been designed to achieve co-triggered in situ cancer drug synthesis and gene therapy by using MOF encapsulated with DNAzyme, minimizing the damage to normal cells.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Biochemistry & Molecular Biology

Transition metal catalysts for the bioorthogonal synthesis of bioactive agents

Melissa O. N. van de L'isle et al.

Summary: The incorporation of abiotic transition metal catalysis into the field of chemical biology has expanded the bioorthogonal chemistry toolbox, with a variety of catalysts showing compatibility with physiological conditions and stability in complex environments. Current trends focus on exploring new metals and advanced catalytic devices, as well as integrating subcellular, cell- and site-targeting capabilities for novel biomedical applications. Transition metals play an increasing role in the controlled release of therapeutics, highlighting their potential in the field.

CURRENT OPINION IN CHEMICAL BIOLOGY (2021)

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Article Chemistry, Physical

Tools and Methods for Investigating Synthetic Metal-Catalyzed Reactions in Living Cells

Dat P. Nguyen et al.

Summary: Research on intracellular catalysis requires an interdisciplinary approach and state-of-the-art instruments. The lack of quantitative data has somewhat hindered progress in catalyst development, but recent advances in characterization methods may help overcome these limitations. Intracellular catalysis has great potential for future biotechnologies and therapeutics.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Unleashing the Power of Bond Cleavage Chemistry in Living Systems

Jie Wang et al.

Summary: Bioorthogonal cleavage chemistry, as a powerful tool for manipulation and gain-of-function studies of biomolecules, has opened up new possibilities for rescuing small molecules and biomacromolecules, allowing multidimensional control over biological processes.

ACS CENTRAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N-H Carbene Insertions

Sara Gutierrez et al.

Summary: Implementing catalytic organometallic transformations in living settings can provide unprecedented opportunities in chemical biology and medicine. This study demonstrated the feasibility of metal carbene transfer reactions in live mammalian cells, highlighting the potential for expanding the repertoire of life-compatible abiotic reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Inorganic & Nuclear

Iridium-Triggered Allylcarbamate Uncaging in Living Cells

Neelu Singh et al.

Summary: A non-toxic organoiridium complex has been developed for the successful uncaging of allyloxycarbonyl-protected amines in biological conditions and living cells, demonstrating potential applications in generating diagnostic and therapeutic agents within HeLa cells. This advancement provides a valuable tool for a wide range of biological and therapeutic applications.

INORGANIC CHEMISTRY (2021)

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Article Multidisciplinary Sciences

Bioorthogonal chemistry

Samuel L. Scinto et al.

Summary: Bioorthogonal chemistry involves high-yielding chemical reactions in biological environments that are rapid and selective, playing essential roles in various fields such as biomedical imaging and drug delivery. Its applications are diverse and include genetic code expansion, drug target identification, and antibody-drug conjugation.

NATURE REVIEWS METHODS PRIMERS (2021)

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Article Chemistry, Physical

Highly Stereoselective Synthesis of Fused Cyclopropane-γ-Lactams via Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation

Xinkun Ren et al.

ACS CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Intracellular Activation of Bioorthogonal Nanozymes through Endosomal Proteolysis of the Protein Corona

Xianzhi Zhang et al.

ACS NANO (2020)

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Article Chemistry, Multidisciplinary

Near-Infrared Light Dual-Promoted Heterogeneous Copper Nanocatalyst for Highly Efficient Bioorthogonal Chemistry in Vivo

Yawen You et al.

ACS NANO (2020)

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Article Chemistry, Multidisciplinary

Intracellular Reactions Promoted by Bis(histidine) Miniproteins Stapled Using Palladium(II) Complexes

Soraya Learte-Aymami et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Intracellular Ruthenium-Promoted (2+2+2) Cycloadditions

Joan Miguel-Avila et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Neutrophil-Membrane-Directed Bioorthogonal Synthesis of Inflammation-Targeting Chiral Drugs

Zhi Du et al.

CHEM (2020)

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Article Chemistry, Multidisciplinary

Bioorthogonal release of anticancer drugs via gold-triggered 2-alkynylbenzamide cyclization

Kenward Vong et al.

CHEMICAL SCIENCE (2020)

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Review Chemistry, Multidisciplinary

Recent Fascinating Aspects of the CuAAC Click Reaction

Morten Meldal et al.

TRENDS IN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

A Biocompatible Heterogeneous MOF-Cu Catalyst for In Vivo Drug Synthesis in Targeted Subcellular Organelles

Faming Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed Redox Isomerizations inside Living Cells

Cristian Vidal et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Physical

Biocompatibility and therapeutic potential of glycosylated albumin artificial metalloenzymes

Shohei Eda et al.

NATURE CATALYSIS (2019)

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Article Biochemistry & Molecular Biology

Fitness Factors for Bioorthogonal Chemical Probes

Yulin Tian et al.

ACS CHEMICAL BIOLOGY (2019)

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Article Multidisciplinary Sciences

An artificial metalloenzyme biosensor can detect ethylene gas in fruits and Arabidopsis leaves

Kenward Vong et al.

NATURE COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Receptor-Based Artificial Metalloenzymes on Living Human Cells

Wadih Ghattas et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Asymmetric transfer hydrogenation by synthetic catalysts in cancer cells

James P. C. Coverdale et al.

NATURE CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Discrete Cu(I) complexes for azide-alkyne annulations of small molecules inside mammalian cells

Joan Miguel-Avila et al.

CHEMICAL SCIENCE (2018)

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Article Multidisciplinary Sciences

A cell-penetrating artificial metalloenzyme regulates a gene switch in a designer mammalian cell

Yasunori Okamoto et al.

NATURE COMMUNICATIONS (2018)

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Article Multidisciplinary Sciences

Concurrent and orthogonal gold(I) and ruthenium (II) catalysis inside living cells

Cristian Vidal et al.

NATURE COMMUNICATIONS (2018)

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Article Multidisciplinary Sciences

Designed heterogeneous palladium catalysts for reversible light-controlled bioorthogonal catalysis in living cells

Faming Wang et al.

NATURE COMMUNICATIONS (2018)

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Article Chemistry, Physical

Nanocopper-Doped Cross-Linked Lipoic Acid Nanoparticles for Morphology-Dependent Intracellular Catalysis

Jingsheng Huang et al.

ACS CATALYSIS (2018)

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Article Chemistry, Physical

An artificial metalloenzyme for carbene transfer based on a biotinylated dirhodium anchored within streptavidin

Jingming Zhao et al.

CATALYSIS SCIENCE & TECHNOLOGY (2018)

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Article Chemistry, Multidisciplinary

Olefin Metathesis-Based Fluorescent Probes for the Selective Detection of Ethylene in Live Cells

Sacha N. W. Toussaint et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

On-cell catalysis by surface engineering of live cells with an artificial metalloenzyme

Mathieu Szponarski et al.

COMMUNICATIONS CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Intracellular Transfer Hydrogenation Mediated by Unprotected Organoiridium Catalysts

Sohini Bose et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Multidisciplinary Sciences

Nano-palladium is a cellular catalyst for in vivo chemistry

Miles A. Miller et al.

NATURE COMMUNICATIONS (2017)

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Article Chemistry, Multidisciplinary

Gold-Triggered Uncaging Chemistry in Living Systems

Ana M. Perez-Lopez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Review Chemistry, Multidisciplinary

Inverse electron demand Diels-Alder reactions in chemical biology

B. L. Oliveira et al.

CHEMICAL SOCIETY REVIEWS (2017)

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Article Chemistry, Multidisciplinary

A Highly Efficient Single-Chain Metal Organic Nanoparticle Catalyst for Alkyne-Azide Click Reactions in Water and in Cells

Yugang Bai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Multidisciplinary Sciences

Directed evolution of artificial metalloenzymes for in vivo metathesis

Markus Jeschek et al.

NATURE (2016)

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Article Multidisciplinary Sciences

Transition metal catalysis in the mitochondria of living cells

Maria Tomas-Gamasa et al.

NATURE COMMUNICATIONS (2016)

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Article Chemistry, Multidisciplinary

Supramolecular regulation of bioorthogonal catalysis in cells using nanoparticle-embedded transition metal catalysts

Gulen Yesilbag Tonga et al.

NATURE CHEMISTRY (2015)

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Article Biochemistry & Molecular Biology

A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface

Nan Li et al.

ACS CHEMICAL BIOLOGY (2015)

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Review Biochemistry & Molecular Biology

Finding the Right (Bioorthogonal) Chemistry

David M. Patterson et al.

ACS CHEMICAL BIOLOGY (2014)

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Article Chemistry, Multidisciplinary

Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media

Valentina Bevilacqua et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Progress towards Bioorthogonal Catalysis with Organometallic Compounds

Timo Voelker et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Metal-catalyzed uncaging of DNA-binding agents in living cells

Mateo I. Sanchez et al.

CHEMICAL SCIENCE (2014)

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Article Multidisciplinary Sciences

Biocompatible click chemistry enabled compartment-specific pH measurement inside E-coli

Maiyun Yang et al.

NATURE COMMUNICATIONS (2014)

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Article Chemistry, Multidisciplinary

Ligand-Free Palladium-Mediated Site-Specific Protein Labeling Inside Gram-Negative Bacterial Pathogens

Jie Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Article Biochemistry & Molecular Biology

A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo

Pedro S. Coelho et al.

NATURE CHEMICAL BIOLOGY (2013)

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Article Biochemistry & Molecular Biology

Catalytic Azide Reduction in Biological Environments

Pijus K. Sasmal et al.

CHEMBIOCHEM (2012)

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Article Chemistry, Multidisciplinary

Exploiting the higher alkynophilicity of Au-species: development of a highly selective fluorescent probe for gold ions

Nitin T. Patil et al.

CHEMICAL COMMUNICATIONS (2012)

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Review Chemistry, Multidisciplinary

From Mechanism to Mouse: A Tale of Two Bioorthogonal Reactions

Ellen M. Sletten et al.

ACCOUNTS OF CHEMICAL RESEARCH (2011)

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Article Chemistry, Multidisciplinary

Copper-Free Sonogashira Cross-Coupling for Functionalization of Alkyne-Encoded Proteins in Aqueous Medium and in Bacterial Cells

Nan Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Article Chemistry, Multidisciplinary

Cellular Consequences of Copper Complexes Used To Catalyze Bioorthogonal Click Reactions

David C. Kennedy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Article Chemistry, Multidisciplinary

Palladium-mediated intracellular chemistry

Rahimi M. Yusop et al.

NATURE CHEMISTRY (2011)

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Article Biochemistry & Molecular Biology

Live-Cell Imaging of Cellular Proteins by a Strain-Promoted Azide-Alkyne Cycloaddition

Kimberly E. Beatty et al.

CHEMBIOCHEM (2010)

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Article Chemistry, Organic

Reaction-Based Fluorescent Sensing of Au(I)/Au(III) Species: Mechanistic Implications on Vinylgold Intermediates

Olga A. Egorova et al.

ORGANIC LETTERS (2010)

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Article Chemistry, Organic

A Rationally Designed Fluorescence Turn-On Probe for the Gold(III) Ion

Jung Ho Do et al.

ORGANIC LETTERS (2010)

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Review Chemistry, Multidisciplinary

Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

Ellen M. Sletten et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Multidisciplinary

BIO- AND AIR-TOLERANT CARBON-CARBON BOND FORMATIONS VIA ORGANOMETALLIC RUTHENIUM CATALYSIS

Louis Adriaenssens et al.

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS (2009)

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Article Chemistry, Organic

A Gold(III) Ion-Selective Fluorescent Probe and Its Application to Bioimagings

Young-Keun Yang et al.

ORGANIC LETTERS (2009)

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Article Chemistry, Multidisciplinary

Ruthenium-induced allylcarbamate cleavage in living cells

Craig Streu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Article Chemistry, Multidisciplinary

Fluorescence visualization of newly synthesized proteins in mammalian cells

Kimberly E. Beatty et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Article Chemistry, Organic

Polytriazoles as copper(I)-stabilizing ligands in catalysis

TR Chan et al.

ORGANIC LETTERS (2004)

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Article Chemistry, Multidisciplinary

A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems

NJ Agard et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Multidisciplinary Sciences

A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation

HC Hang et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2003)

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Article Chemistry, Multidisciplinary

Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition

AJ Link et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

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Review Pharmacology & Pharmacy

Copper toxicity, oxidative stress, and antioxidant nutrients

LM Gaetke et al.

TOXICOLOGY (2003)

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Article Multidisciplinary Sciences

Cell surface engineering by a modified Staudinger reaction

E Saxon et al.

SCIENCE (2000)

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Metal-promoted synthetic chemistry within living cells

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