Cleavable linkers in chemical biology.

Interest in cleavable linkers is growing due to the rapid development and expansion of chemical biology. The chemical constrains imposed by the biological conditions cause significant challenges for organic chemists. In this review we will present an overview of the cleavable linkers used in chemical biology classified according to their cleavage conditions by enzymes, nucleophilic/basic reagents, reducing agents, photo-irradiation, electrophilic/acidic reagents, organometallic and metal reagents, oxidizing reagents.

[1]  D. Parry,et al.  Subfilamentous Protofibril Structures in Fibrous Proteins , 2001, The Journal of Biological Chemistry.

[2]  Benjamin F. Cravatt,et al.  Genomics and proteomics: From genes to function: advances in applications of chemical and systems biology , 2007 .

[3]  Y. Leung,et al.  A highly selective FRET-based fluorescent probe for detection of cysteine and homocysteine. , 2010, Chemistry.

[4]  Ralph Weissleder,et al.  A novel method for imaging apoptosis using a caspase-1 near-infrared fluorescent probe. , 2004, Neoplasia.

[5]  F. Kratz,et al.  A novel method for coupling doxorubicin to lactosaminated human albumin by an acid sensitive hydrazone bond: synthesis, characterization and preliminary biological properties of the conjugate. , 2004, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[6]  A. Mokhir,et al.  DNA-templated metal catalysis. , 2003, Journal of the American Chemical Society.

[7]  C. Bertozzi,et al.  A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds. , 2000, Organic letters.

[8]  Jacob M Hooker,et al.  Interior surface modification of bacteriophage MS2. , 2004, Journal of the American Chemical Society.

[9]  G. Charron,et al.  Rapid visualization and large-scale profiling of bacterial lipoproteins with chemical reporters. , 2010, Journal of the American Chemical Society.

[10]  P. Scott,et al.  Diversity linker units for solid-phase organic synthesis , 2006 .

[11]  R. Tsien,et al.  Biologically useful chelators that take up calcium(2+) upon illumination , 1989 .

[12]  Y. Sadakane,et al.  Synthesis of Diazirinyl Photoprobe Carrying a Novel Cleavable Biotin , 2005, Chembiochem : a European journal of chemical biology.

[13]  Nondenaturing Chemical Proteomics for Protein Complex Isolation and Identification , 2010, Chembiochem : a European journal of chemical biology.

[14]  J. Engels,et al.  Fluorescent labeling of (oligo)nucleotides by a new fluoride cleavable linker capable of versatile attachment modes. , 2010, Bioconjugate chemistry.

[15]  R Weissleder,et al.  In vivo imaging of proteolytic enzyme activity using a novel molecular reporter. , 2000, Cancer research.

[16]  T. Park,et al.  Novel intracellular delivery system of antisense oligonucleotide by self-assembled hybrid micelles composed of DNA/PEG conjugate and cationic fusogenic peptide. , 2003, Bioconjugate chemistry.

[17]  Z. Xi,et al.  FRET-based fluorescence probes for hydrolysis study and pig liver esterase activity , 2008 .

[18]  T. Morton,et al.  Two-step affinity chromatography. Model systems and an example using biotin-avidin binding and a fluoridolyzable linker , 1991 .

[19]  Li Yang,et al.  A photocleavable and mass spectrometry identifiable cross-linker for protein interaction studies. , 2010, Analytical chemistry.

[20]  T. Iwatsubo,et al.  Development of photoaffinity probes for gamma-secretase equipped with a nitrobenzenesulfonamide-type cleavable linker. , 2009, Bioorganic & medicinal chemistry letters.

[21]  J. J. Starling,et al.  Novel acid labile COL1 trityl-linked difluoronucleoside immunoconjugates: synthesis, characterization, and biological activity. , 1996, Bioconjugate chemistry.

[22]  Teruyuki Nagamune,et al.  A bromocoumarin-based linker for synthesis of photocleavable peptidoconjugates with high photosensitivity. , 2008, Chemical communications.

[23]  B. Cravatt,et al.  A tandem orthogonal proteolysis strategy for high-content chemical proteomics. , 2005, Journal of the American Chemical Society.

[24]  Y. Kageyama,et al.  Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand-receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution. , 2009, Bioorganic & medicinal chemistry.

[25]  Lan Huang,et al.  Profiling of Protein Interaction Networks of Protein Complexes Using Affinity Purification and Quantitative Mass Spectrometry* , 2010, Molecular & Cellular Proteomics.

[26]  Ralph Weissleder,et al.  In vivo molecular target assessment of matrix metalloproteinase inhibition , 2001, Nature Medicine.

[27]  J. Fei,et al.  pH-responsive polysaccharide microcapsules through covalent bonding assembly. , 2011, Chemical communications.

[28]  Omid C Farokhzad,et al.  pH-Responsive nanoparticles for drug delivery. , 2010, Molecular pharmaceutics.

[29]  J. Bruce,et al.  Collisionally activated dissociation and electron capture dissociation of several mass spectrometry-identifiable chemical cross-linkers. , 2006, Analytical chemistry.

[30]  Daniel Scherman,et al.  pH-sensitive PEG lipids containing orthoester linkers: new potential tools for nonviral gene delivery. , 2004, Journal of controlled release : official journal of the Controlled Release Society.

[31]  Spencer J. Williams,et al.  Active-site Peptide “Fingerprinting” of Glycosidases in Complex Mixtures by Mass Spectrometry , 2005, Journal of Biological Chemistry.

[32]  C. Bertozzi,et al.  Cell surface engineering by a modified Staudinger reaction. , 2000, Science.

[33]  J. Olejnik,et al.  Photocleavable peptide-DNA conjugates: synthesis and applications to DNA analysis using MALDI-MS. , 1999, Nucleic acids research.

[34]  A J Lomant,et al.  Chemical probes of extended biological structures: synthesis and properties of the cleavable protein cross-linking reagent [35S]dithiobis(succinimidyl propionate). , 1976, Journal of molecular biology.

[35]  D. Neville,et al.  New protein cross-linking reagents that are cleaved by mild acid. , 1989, Biochemistry.

[36]  N. Nesnas,et al.  A cleavable affinity biotinylating agent reveals a retinoid binding role for RPE65. , 2003, Biochemistry.

[37]  H. Overkleeft,et al.  A cleavable linker based on the levulinoyl ester for activity-based protein profiling. , 2010, Angewandte Chemie.

[38]  C. Bertozzi,et al.  A FRET-based fluorogenic phosphine for live-cell imaging with the Staudinger ligation. , 2008, Angewandte Chemie.

[39]  Miriam Scadeng,et al.  Surgery with molecular fluorescence imaging using activatable cell-penetrating peptides decreases residual cancer and improves survival , 2010, Proceedings of the National Academy of Sciences.

[40]  Christoph H Borchers,et al.  Isotopically Coded Cleavable Cross-linker for Studying Protein-Protein Interaction and Protein Complexes* , 2005, Molecular & Cellular Proteomics.

[41]  D. Thompson,et al.  Acid-triggered release via dePEGylation of DOPE liposomes containing acid-labile vinyl ether PEG-lipids. , 2003, Journal of controlled release : official journal of the Controlled Release Society.

[42]  A. Berkessel,et al.  Fluorescence Reporters for Phosphodiesterase Activity , 1997 .

[43]  N. Hampp,et al.  Phototriggered release of photolabile drugs via two‐photon absorption‐induced cleavage of polymer‐bound dicoumarin , 2007 .

[44]  D. Boturyn,et al.  Activatable probes for non-invasive small animal fluorescence imaging , 2007 .

[45]  Kazunori Kataoka,et al.  Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile beta-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells. , 2005, Journal of the American Chemical Society.

[46]  A. Heck,et al.  Development of a Novel Chemical Probe for the Selective Enrichment of Phosphorylated Serine‐ and Threonine‐Containing Peptides , 2005, Chembiochem : a European journal of chemical biology.

[47]  H. Hang,et al.  Bioorthogonal chemical reporters for monitoring protein acetylation. , 2010, Journal of the American Chemical Society.

[48]  C. Che,et al.  Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containing peptides in aqueous medium. , 2009, Chemistry.

[49]  Ki Duk Park,et al.  Useful tools for biomolecule isolation, detection, and identification: acylhydrazone-based cleavable linkers. , 2009, Chemistry & biology.

[50]  M. Cheung,et al.  3- AND 4-NITROBENZENESULFONAMIDES : EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY AMINES AND PROTECTION OF AMINES , 1995 .

[51]  Orthogonal alkynyl amino acid reporter for selective labeling of bacterial proteomes during infection. , 2010, Angewandte Chemie.

[52]  B. J. Backes,et al.  An Alkanesulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis , 1999 .

[53]  Y. Hatanaka,et al.  Synthesis and evaluation of novel photoreactive alpha-amino acid analog carrying acidic and cleavable functions. , 2009, Bioorganic & medicinal chemistry letters.

[54]  Robert Langer,et al.  Poly(ethylene glycol) with observable shedding. , 2010, Angewandte Chemie.

[55]  Joshua E. Elias,et al.  Catch-and-release reagents for broadscale quantitative proteomics analyses. , 2007, Journal of proteome research.

[56]  D. Campopiano,et al.  Synthesis and application of a new cleavable linker for "click"-based affinity chromatography. , 2010, Organic & biomolecular chemistry.

[57]  Yasuteru Urano,et al.  Design and synthesis of an enzyme activity-based labeling molecule with fluorescence spectral change. , 2006, Journal of the American Chemical Society.

[58]  J R Griffiths,et al.  Causes and consequences of tumour acidity and implications for treatment. , 2000, Molecular medicine today.

[59]  T. P. Sullivan,et al.  Reactions on Monolayers: Organic Synthesis in Two Dimensions , 2003 .

[60]  Development of an indole-based chemically cleavable linker concept for immobilizing bait compounds for protein pull-down experiments. , 2011, Bioconjugate chemistry.

[61]  T. Muir,et al.  Probing the chemical basis of binding activity in an SH3 domain by protein signature analysis. , 1996, Chemistry & biology.

[62]  S. Bräse The virtue of the multifunctional triazene linkers in the efficient solid-phase synthesis of heterocycle libraries. , 2004, Accounts of chemical research.

[63]  T. Kigawa,et al.  Regioselective Carbon–Carbon Bond Formation in Proteins with Palladium Catalysis; New Protein Chemistry by Organometallic Chemistry , 2006, Chembiochem : a European journal of chemical biology.

[64]  Wei Zhang,et al.  Improving anticancer activity and selectivity of camptothecin through conjugation with releasable substance P. , 2011, Bioorganic & medicinal chemistry letters.

[65]  B. V. Timokhin,et al.  Levulinic acid in organic synthesis , 1999 .

[66]  Spencer J. Williams,et al.  Synthesis and Testing of Mechanism‐Based Protein‐Profiling Probes for Retaining Endo‐glycosidases , 2006, Chembiochem : a European journal of chemical biology.

[67]  O. Jahn,et al.  The binding protein of corticotropin-releasing factor: Ligand-binding site and subunit structure , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[68]  J. Shabanowitz,et al.  Enrichment and Site Mapping of O-Linked N-Acetylglucosamine by a Combination of Chemical/Enzymatic Tagging, Photochemical Cleavage, and Electron Transfer Dissociation Mass Spectrometry* , 2009, Molecular & Cellular Proteomics.

[69]  D. Boturyn,et al.  Activatable Fluorescent Probes for Tumour‐Targeting Imaging in Live Mice , 2006, ChemMedChem.

[70]  Preparation of oligonucleotide-biotin conjugates with cleavable linkers. , 1995, Bioconjugate chemistry.

[71]  N. Murthy,et al.  Polyketal nanoparticles: a new pH-sensitive biodegradable drug delivery vehicle. , 2005, Bioconjugate chemistry.

[72]  M. Bogyo,et al.  Activity-based probes as a tool for functional proteomic analysis of proteases , 2008, Expert review of proteomics.

[73]  V. Barton,et al.  Rationale design of biotinylated antimalarial endoperoxide carbon centered radical prodrugs for applications in proteomics. , 2010, Journal of medicinal chemistry.

[74]  D. Predescu,et al.  Endothelial transcytotic machinery involves supramolecular protein-lipid complexes. , 2001, Molecular biology of the cell.

[75]  J. Brodbelt,et al.  Chromogenic cross-linker for the characterization of protein structure by infrared multiphoton dissociation mass spectrometry. , 2008, Analytical chemistry.

[76]  Juan L. Vivero-Escoto,et al.  Photoinduced intracellular controlled release drug delivery in human cells by gold-capped mesoporous silica nanosphere. , 2009, Journal of the American Chemical Society.

[77]  L. Babe,et al.  Viral Proteases: Evolution of Diverse Structural Motifs to Optimize Function , 1997, Cell.

[78]  M. Bogyo,et al.  Tagging and detection strategies for activity-based proteomics. , 2007, Current opinion in chemical biology.

[79]  Scott E. Fraser,et al.  In vivo visualization of gene expression using magnetic resonance imaging , 2000, Nature Biotechnology.

[80]  The removal of fluorescence in sequencing-by-synthesis. , 2009, Biochemical and biophysical research communications.

[81]  T. Cech,et al.  Oxytricha telomere-binding protein: DNA-dependent dimerization of the alpha and beta subunits. , 1993, Proceedings of the National Academy of Sciences of the United States of America.

[82]  J. Bruce,et al.  A new maleimide-bound acid-cleavable solid-support reagent for profiling phosphorylation. , 2005, Rapid communications in mass spectrometry : RCM.

[83]  J. A. Fernandez,et al.  Manipulation of thrombin exosite I, by ligand‐directed covalent modification , 2007, Journal of thrombosis and haemostasis : JTH.

[84]  Ralph Weissleder,et al.  Optical Visualization of Cathepsin K Activity in Atherosclerosis With a Novel, Protease-Activatable Fluorescence Sensor , 2007, Circulation.

[85]  M. Remm,et al.  Fluoride-Cleavable, Fluorescently Labelled Reversible Terminators: Synthesis and Use in Primer Extension , 2011, Chemistry.

[86]  Edward W. Tate,et al.  Getting a chemical handle on protein post-translational modification. , 2010, Organic & biomolecular chemistry.

[87]  M. Bradley,et al.  Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. , 2000, Chemical reviews.

[88]  B. Cravatt,et al.  Activity-based protein profiling: from enzyme chemistry to proteomic chemistry. , 2008, Annual review of biochemistry.

[89]  Daniela C Dieterich,et al.  Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT). , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[90]  C. Holmes Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. , 1997, The Journal of organic chemistry.

[91]  R. Krämer,et al.  Templated metal catalysis for single nucleotide specific DNA sequence detection. , 2005, Journal of the American Chemical Society.

[92]  T. Kan,et al.  2,4-Dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines , 1997 .

[93]  F M Richards,et al.  Chemical cross-linking: reagents and problems in studies of membrane structure. , 1977, Annual review of biochemistry.

[94]  J. Kopeček,et al.  Intracellular targeting of polymer-bound drugs for cancer chemotherapy. , 2005, Advanced drug delivery reviews.

[95]  Identification of cross-linked amino acids in the protein pair HmaL23-HmaL29 from the 50S ribosomal subunit of the archaebacterium Haloarcula marismortui. , 1993, Biochemistry.

[96]  K. Medzihradszky,et al.  Enrichment of O-GlcNAc modified proteins by the periodate oxidation-hydrazide resin capture approach. , 2010, Journal of proteome research.

[97]  Martin Kussmann,et al.  Chemical cross‐linking with thiol‐cleavable reagents combined with differential mass spectrometric peptide mapping—A novel approach to assess intermolecular protein contacts , 2000, Protein science : a publication of the Protein Society.

[98]  P. Herdewijn,et al.  Cleavage of DNA without loss of genetic information by incorporation of a disaccharide nucleoside. , 2003, Nucleic acids research.

[99]  G. Charron,et al.  Comparative analysis of cleavable azobenzene-based affinity tags for bioorthogonal chemical proteomics. , 2010, Chemistry & biology.

[100]  R. Tsien,et al.  Activatable cell penetrating peptides linked to nanoparticles as dual probes for in vivo fluorescence and MR imaging of proteases , 2010, Proceedings of the National Academy of Sciences.

[101]  Yoshihisa Suzuki,et al.  Thrombin-Sensitive Peptide Linkers for Biological Signal-Responsive Drug Release Systems , 1998, Peptides.

[102]  K. Kataoka,et al.  pH-responsive oligodeoxynucleotide (ODN)-poly(ethylene glycol) conjugate through acid-labile beta-thiopropionate linkage: preparation and polyion complex micelle formation. , 2003, Biomacromolecules.

[103]  I. Fournier,et al.  Tag-mass: specific molecular imaging of transcriptome and proteome by mass spectrometry based on photocleavable tag. , 2007, Journal of proteome research.

[104]  Shiyue Fang,et al.  Scalable synthetic oligodeoxynucleotide purification with use of a catching by polymerization, washing, and releasing approach. , 2010, Organic letters.

[105]  M. Karol,et al.  Intra- and intermolecular reactions of 4,4'-diisocyanatodiphenylmethane with human serum albumin. , 1988, Chemical research in toxicology.

[106]  Jinbo Li,et al.  Chemistry and biological applications of photo-labile organic molecules. , 2010, Chemical Society reviews.

[107]  P. Senter,et al.  New heterobifunctional protein cross linking reagent that forms an acid labile link , 1985 .

[108]  L. J. Mueller,et al.  pH-responsive nanogated ensemble based on gold-capped mesoporous silica through an acid-labile acetal linker. , 2010, Journal of the American Chemical Society.

[109]  K. Johnsson,et al.  Photoactivatable and photoconvertible fluorescent probes for protein labeling. , 2010, ACS chemical biology.

[110]  J. DeSimone,et al.  Tunable bifunctional silyl ether cross-linkers for the design of acid-sensitive biomaterials. , 2010, Journal of the American Chemical Society.

[111]  P. Couvreur,et al.  Prodrug-based intracellular delivery of anticancer agents. , 2011, Advanced drug delivery reviews.

[112]  J. F. Stoddart,et al.  pH-operated nanopistons on the surfaces of mesoporous silica nanoparticles. , 2010, Journal of the American Chemical Society.

[113]  O. Buchardt,et al.  The oxidative cleavability of protein cross-linking reagents containing organoselenium bridges. , 1990, Bioconjugate chemistry.

[114]  G. Charron,et al.  Palmitoylome profiling reveals S-palmitoylation-dependent antiviral activity of IFITM3. , 2010, Nature chemical biology.

[115]  Ruedi Aebersold,et al.  Quantitative Proteome Analysis by Solid-phase Isotope Tagging and Mass Spectrometry Beads Photocleavable Linker Isotope Tag Reactive Group , 2022 .

[116]  I. Tannock,et al.  Acid pH in tumors and its potential for therapeutic exploitation. , 1989, Cancer research.

[117]  C. Tung,et al.  Proteolysis: a biological process adapted in drug delivery, therapy, and imaging. , 2009, Bioconjugate chemistry.

[118]  Lin Yuan,et al.  Construction of a FRET-based ratiometric fluorescent thiol probe. , 2011, Chemical communications.

[119]  Günter Mayer,et al.  Biologically active molecules with a "light switch". , 2006, Angewandte Chemie.

[120]  Identification of a cross-link in the Escherichia coli ribosomal protein pair S13-S19 at the amino acid level. , 1988, The Journal of biological chemistry.

[121]  G. Blobel,et al.  125I-labeled crosslinking reagent that is hydrophilic, photoactivatable, and cleavable through an azo linkage. , 1984, Proceedings of the National Academy of Sciences of the United States of America.

[122]  P. Dawson,et al.  Bisaryl hydrazones as exchangeable biocompatible linkers. , 2010, Angewandte Chemie.

[123]  W. Shen,et al.  cis-Aconityl spacer between daunomycin and macromolecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. , 1981, Biochemical and biophysical research communications.

[124]  Michael E. Hahn,et al.  Simultaneous triggering of protein activity and fluorescence. , 2004, Journal of the American Chemical Society.

[125]  Tetsuo Nagano,et al.  Hypoxia-sensitive fluorescent probes for in vivo real-time fluorescence imaging of acute ischemia. , 2010, Journal of the American Chemical Society.

[126]  C. Jaffe,et al.  New clevable photoreactive heterobifunctional cross-linking reagents for studying membrane organization. , 1980, Biochemistry.

[127]  J. Levy,et al.  A chemically cleavable biotinylated nucleotide: usefulness in the recovery of protein-DNA complexes from avidin affinity columns. , 1985, Proceedings of the National Academy of Sciences of the United States of America.

[128]  V. Gerke,et al.  The Acidic C-terminal Domain of rna1p Is Required for the Binding of Ran·GTP and for RanGAP Activity* , 1997, The Journal of Biological Chemistry.

[129]  Y. Urano,et al.  Design and synthesis of an enzyme-cleavable sensor molecule for phosphodiesterase activity based on fluorescence resonance energy transfer. , 2002, Journal of the American Chemical Society.

[130]  M. Bogyo,et al.  A mild chemically cleavable linker system for functional proteomic applications. , 2007, Angewandte Chemie.

[131]  Daniela C Dieterich,et al.  Cleavable biotin probes for labeling of biomolecules via azide-alkyne cycloaddition. , 2010, Journal of the American Chemical Society.

[132]  Bernard Testa,et al.  Prodrugs: bridging pharmacodynamic/pharmacokinetic gaps. , 2009, Current opinion in chemical biology.

[133]  A. Gemeay Kinetics and mechanism of the reduction of some azo-dyes by inorganic oxysulfur compounds , 2002 .

[134]  Wanyi Tai,et al.  Prodrugs for improving tumor targetability and efficiency. , 2011, Advanced drug delivery reviews.

[135]  S. Sieber,et al.  A photolabile linker for the mild and selective cleavage of enriched biomolecules from solid support. , 2009, The Journal of organic chemistry.

[136]  C. Hou,et al.  A cross-linking study of the Ca2+, Mg2+-activated adenosine triphosphatase of Escherichia coli. , 1980, European journal of biochemistry.

[137]  K. G. Rajeev,et al.  Lipophilic siRNAs mediate efficient gene silencing in oligodendrocytes with direct CNS delivery. , 2010, Journal of controlled release : official journal of the Controlled Release Society.

[138]  F. Kratz,et al.  Development of protein-binding bifunctional linkers for a new generation of dual-acting prodrugs. , 2009, Bioconjugate chemistry.

[139]  R. Traut,et al.  Disulfide cross-linking of Escherichia coli ribosomal proteins with 2-iminothiolane (methyl 4-mercaptobutyrimidate): evidence that the cross-linked protein pairs are formed in the intact ribosomal subunit. , 1978, Biochemistry.

[140]  Design and synthesis of a chemically cleavable fluorescent nucleotide, 3'-O-allyl-dGTP-allyl-bodipy-FL-510, as a reversible terminator for DNA sequencing by synthesis. , 2006, Journal of the American Chemical Society.

[141]  G. Heavner,et al.  Synthesis of a new photolabile support. 4-(2-Chloropropionyl)phenylacetamidomethyl-resin and its application in solid-phase peptide synthesis , 1983 .

[142]  Theodora W. Greene,et al.  Greene's Protective Groups in Organic Synthesis , 2006 .

[143]  P. K. Smith,et al.  A new cleavable reagent for cross-linking and reversible immobilization of proteins. , 1979, Biochemical and biophysical research communications.

[144]  F. Bach,et al.  Mapping of lymphocyte surface polypeptide antigens by chemical cross-linking with BSOCOES. , 1980, Journal of Immunology.

[145]  A. Okamoto,et al.  Phototriggered drug release from functionalized oligonucleotides by a molecular beacon strategy. , 2003, Angewandte Chemie.

[146]  R. Aebersold,et al.  Probing Native Protein Structures by Chemical Cross-linking, Mass Spectrometry, and Bioinformatics , 2010, Molecular & Cellular Proteomics.

[147]  D. Bergstrom,et al.  Fluoride-cleavable biotinylation phosphoramidite for 5'-end-labeling and affinity purification of synthetic oligonucleotides. , 2003, Nucleic Acids Research.

[148]  A. Wagner,et al.  Optimization of the Azobenzene Scaffold for Reductive Cleavage by Dithionite; Development of an Azobenzene Cleavable Linker for Proteomic Applications , 2010 .

[149]  Erin E. Carlson,et al.  Chemoselective probes for metabolite enrichment and profiling , 2007, Nature Methods.

[150]  Irving E. Vega,et al.  Synthesis of acid-cleavable light isotope-coded affinity tags (ICAT-L) for potential use in proteomic expression profiling analysis. , 2006, Bioconjugate chemistry.

[151]  Christoph H Borchers,et al.  BiPS, a Photocleavable, Isotopically Coded, Fluorescent Cross-linker for Structural Proteomics * , 2009, Molecular & Cellular Proteomics.

[152]  Gonen Ashkenasy,et al.  Light induced drug delivery into cancer cells. , 2011, Biomaterials.

[153]  Yong-Kweon Kim,et al.  Microbead‐based affinity chromatography chip using RNA aptamer modified with photocleavable linker , 2004, Electrophoresis.

[154]  J. Brockmöller,et al.  Cross-linked amino acids in the protein pair S13-S19 and sequence analysis of protein S13 of Bacillus stearothermophilus ribosomes. , 1988, Biochemistry.

[155]  Yujiang Fan,et al.  In Vivo Evaluation of a pH‐Sensitive Pullulan–Doxorubicin Conjugate , 2010 .

[156]  F. Dahlquist,et al.  Cross-linking of ubiquinone cytochrome c reductase (complex III) with periodate-cleavable bifunctional reagents. , 1978, Biochemistry.

[157]  T. Brown,et al.  Rapid mass spectrometric identification of human genomic polymorphisms using multiplexed photocleavable mass-tagged probes and solid phase capture. , 2007, Organic & biomolecular chemistry.

[158]  M. Metzker Sequencing technologies — the next generation , 2010, Nature Reviews Genetics.

[159]  G. Zheng,et al.  Design and synthesis of phospholipase C and A2-activatable near-infrared fluorescent smart probes. , 2010, Bioconjugate chemistry.

[160]  H. Fasold,et al.  Bifunctional reagents for the crosslinking of proteins. , 1971, Angewandte Chemie.

[161]  M. Bogyo,et al.  Proteomics Evaluation of Chemically Cleavable Activity-based Probes* , 2007, Molecular & Cellular Proteomics.

[162]  J W Hershey,et al.  Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome. , 1973, Biochemistry.