click chemistry

Summary

Summary: Organic chemistry methodology that mimics the modular nature of various biosynthetic processes. It uses highly reliable and selective reactions designed to "click" i.e., rapidly join small modular units together in high yield, without offensive byproducts. In combination with COMBINATORIAL CHEMISTRY TECHNIQUES, it is used for the synthesis of new compounds and combinatorial libraries.

Top Publications

  1. Thirumurugan P, Matosiuk D, Jozwiak K. Click chemistry for drug development and diverse chemical-biology applications. Chem Rev. 2013;113:4905-79 pubmed publisher
  2. Kato A, Kuratani M, Yanagisawa T, Ohtake K, Hayashi A, Amano Y, et al. Extensive Survey of Antibody Invariant Positions for Efficient Chemical Conjugation Using Expanded Genetic Codes. Bioconjug Chem. 2017;28:2099-2108 pubmed publisher
    ..These results showed that our approach greatly enhanced the availability of antibodies for chemical conjugation and might aid in the development of new therapeutic antibodies...
  3. Senkevich T, Katsafanas G, Weisberg A, Olano L, Moss B. Identification of Vaccinia Virus Replisome and Transcriptome Proteins by Isolation of Proteins on Nascent DNA Coupled with Mass Spectrometry. J Virol. 2017;91: pubmed publisher
    ..We adapted newly developed procedures for click chemistry and iPOND (Isolation of proteins on nascent DNA) to investigate vaccinia ..
  4. Kiliszek A, Blaszczyk L, Kierzek R, Rypniewski W. Stabilization of RNA hairpins using non-nucleotide linkers and circularization. Nucleic Acids Res. 2017;45:e92 pubmed publisher
    ..Another method uses click chemistry to stitch the RNA ends with a triazole linker. Both techniques are efficient and easy to perform...
  5. Viswanath V, Santhakumar K. Perspectives on dendritic architectures and their biological applications: From core to cell. J Photochem Photobiol B. 2017;173:61-83 pubmed publisher
    ..This paper highlights the fascinating theoretical advances and principal mechanisms of dendrimer synthesis and their ability to capture light that strengthens its applicability from radiant energy to medical photonics. ..
  6. Fernandez M, Freed E. "Expand and Click": A New Method for Labeling HIV-1 Envelope Glycoproteins. Cell Chem Biol. 2017;24:548-550 pubmed publisher
    ..Env) glycoprotein complex by using genetic code expansion, bioorthogonal amino acids, synthetic dyes, and click chemistry. This minimally invasive approach allows the measurement of native Env cellular distribution and dynamics.
  7. Zeng D, Kuang G, Wang S, Peng W, Lin S, Zhang Q, et al. Discovery of Novel 11-Triazole Substituted Benzofuro[3,2-b]quinolone Derivatives as c-myc G-Quadruplex Specific Stabilizers via Click Chemistry. J Med Chem. 2017;60:5407-5423 pubmed publisher
    ..Our findings broadened the modification strategies of specific G-quadruplex stabilizers. ..
  8. Routh A, Ji P, Jaworski E, Xia Z, Li W, Wagner E. Poly(A)-ClickSeq: click-chemistry for next-generation 3?-end sequencing without RNA enrichment or fragmentation. Nucleic Acids Res. 2017;45:e112 pubmed publisher
    ..Moreover, we utilize PAC-seq to quantify and analyze APA events regulated by CFIm25 illustrating how this technology can be harnessed to identify alternatively polyadenylated RNA. ..
  9. Schneider M, Barnes C, Bryant S. Characterization of the chondrocyte secretome in photoclickable poly(ethylene glycol) hydrogels. Biotechnol Bioeng. 2017;114:2096-2108 pubmed publisher
    ..Biotechnol. Bioeng. 2017;114: 2096-2108. © 2017 Wiley Periodicals, Inc. ..

More Information

Publications56

  1. Hou W, Luo Z, Zhang G, Cao D, Li D, Ruan H, et al. Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids. Eur J Med Chem. 2017;138:1042-1052 pubmed publisher
    ..Preliminary mechanism studies indicated that compound 24 could induce apoptosis in MDA-MB-231 cells and was worth developing into a novel natural product-like anticancer lead by proper structure modification. ..
  2. Bhardwaj A, Kaur J, Wuest M, Wuest F. In situ click chemistry generation of cyclooxygenase-2 inhibitors. Nat Commun. 2017;8:1 pubmed publisher
    ..Herein, with the use of kinetic target-guided synthesis, also termed as in situ click chemistry, we describe the discovery of two highly potent and selective cyclooxygenase-2 isozyme inhibitors...
  3. Yamamura H. Chemical Modification of Cyclodextrin and Amylose by Click Reaction and Its Application to the Synthesis of Poly-alkylamine-Modified Antibacterial Sugars. Chem Pharm Bull (Tokyo). 2017;65:312-317 pubmed publisher
    ..This review will describe the results of our microwave-assisted click reaction for the poly-modification of CD and amylose molecules, and its application to the study of synthetic membrane active antibacterial derivatives. ..
  4. Galibert M, Renaudet O, Dumy P, Boturyn D. Access to biomolecular assemblies through one-pot triple orthogonal chemoselective ligations. Angew Chem Int Ed Engl. 2011;50:1901-4 pubmed publisher
  5. Fu N, Wang S, Zhang Y, Zhang C, Yang D, Weng L, et al. Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design and synthesis as potential antifungal drugs for Candida albicans. Eur J Med Chem. 2017;136:596-602 pubmed publisher
    ..including converting the commercial available alkyl bromide to alkyl azide, consequently with a typical click chemistry method, copper(II) sulfate and sodium ascorbate as catalyst in water to furnish ATCs with mild to good yields...
  6. Wang T, Yuan C, Dai B, Liu Y, Li M, Feng Z, et al. Click-Chemistry-Mediated Rapid Microbubble Capture for Acute Thrombus Ultrasound Molecular Imaging. Chembiochem. 2017;18:1364-1368 pubmed publisher
    ..Tetrazine-modified microbubbles (tetra-MBs) could be uniquely and rapidly captured by subsequent click chemistry of thrombus tagged with a trans-cyclooctene-pretreated CD62p antibody...
  7. Zhang J, Wang J, Lee Y, Lim T, Lin Q, Shen H. Proteomic Profiling of De Novo Protein Synthesis in Starvation-Induced Autophagy Using Bioorthogonal Noncanonical Amino Acid Tagging. Methods Enzymol. 2017;588:41-59 pubmed publisher
    ..We believe that this approach is effective in identification of newly synthesized proteins in the process of autophagy and provides useful insights to the molecular mechanisms and biological functions of autophagy. ..
  8. Yang L, Chumsae C, Kaplan J, Moulton K, Wang D, Lee D, et al. Detection of Alkynes via Click Chemistry with a Brominated Coumarin Azide by Simultaneous Fluorescence and Isotopic Signatures in Mass Spectrometry. Bioconjug Chem. 2017;28:2302-2309 pubmed publisher
    Alkynes are a key component of click chemistry and used for a wide variety of applications including bioconjugation, selective tagging of protein modifications, and labeling of metabolites and drug targets...
  9. Zheng T, Jiang H, Gros M, Del Amo D, Sundaram S, Lauvau G, et al. Tracking N-acetyllactosamine on cell-surface glycans in vivo. Angew Chem Int Ed Engl. 2011;50:4113-8 pubmed publisher
  10. Wang C, Song X, Xiao Y. SNAP-Tag-Based Subcellular Protein Labeling and Fluorescent Imaging with Naphthalimides. Chembiochem. 2017;18:1762-1769 pubmed publisher
    ..naphthalimide-BG derivatives, TNI-BG, QNI-BG, and ONI-BG, were conveniently synthesized through modular "click chemistry" in high yields...
  11. Piras M, Testa A, Fleming I, Dall Angelo S, Andriu A, Menta S, et al. High-Affinity "Click" RGD Peptidomimetics as Radiolabeled Probes for Imaging ?v ?3 Integrin. ChemMedChem. 2017;12:1142-1151 pubmed publisher
    Nonpeptidic Arg-Gly-Asp (RGD)-mimic ligands were designed and synthesized by click chemistry between an arginine-azide mimic and an aspartic acid-alkyne mimic...
  12. Yakushiji F, Muguruma K, Hayashi Y, Shirasaka T, Kawamata R, Tanaka H, et al. Click strategy using disodium salts of amino acids improves the water solubility of plinabulin and KPU-300. Bioorg Med Chem. 2017;25:3623-3630 pubmed publisher
    ..With this flexibility, we are approaching to the in vivo study using water-soluble derivative. ..
  13. Liang K, Such G, Zhu Z, Yan Y, Lomas H, Caruso F. Charge-shifting click capsules with dual-responsive cargo release mechanisms. Adv Mater. 2011;23:H273-7 pubmed publisher
  14. Swiderska K, Szlachcic A, Czyrek A, Zakrzewska M, Otlewski J. Site-specific conjugation of fibroblast growth factor 2 (FGF2) based on incorporation of alkyne-reactive unnatural amino acid. Bioorg Med Chem. 2017;25:3685-3693 pubmed publisher
    ..The detergent-based optimization approach may help overcome problems with the CuAAC reaction yield for protein modification with hydrophobic compounds, such as MMAE. ..
  15. Steinhagen M, Holland Nell K, Meldal M, Beck Sickinger A. Simultaneous "one pot" expressed protein ligation and CuI-catalyzed azide/alkyne cycloaddition for protein immobilization. Chembiochem. 2011;12:2426-30 pubmed publisher
  16. Kitamura Y, Asakura R, Terazawa K, Shibata A, Ikeda M, Kitade Y. Nucleobase azide-ethynylribose click chemistry contributes to stabilizing oligonucleotide duplexes and stem-loop structures. Bioorg Med Chem Lett. 2017;27:2655-2658 pubmed publisher
  17. Dovgan I, Ursuegui S, Erb S, Michel C, Kolodych S, Cianférani S, et al. Acyl Fluorides: Fast, Efficient, and Versatile Lysine-Based Protein Conjugation via Plug-and-Play Strategy. Bioconjug Chem. 2017;28:1452-1457 pubmed publisher
    ..This translates into better control of the DoC and enables the efficient and fast functionalization of delicate biomolecules at low temperature...
  18. Vermonden T, Censi R, Hennink W. Hydrogels for protein delivery. Chem Rev. 2012;112:2853-88 pubmed publisher
  19. Diner I, Dooyema J, Gearing M, Walker L, Seyfried N. Generation of Clickable Pittsburgh Compound B for the Detection and Capture of β-Amyloid in Alzheimer's Disease Brain. Bioconjug Chem. 2017;28:2627-2637 pubmed publisher
  20. Farzan V, Ulashchik E, Martynenko Makaev Y, Kvach M, Aparin I, Brylev V, et al. Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters. Bioconjug Chem. 2017;28:2599-2607 pubmed publisher
    ..The approach is suitable for high-throughput synthesis of oligonucleotide conjugates ranging from fluorescent DNA probes to various multi-GalNAc derivatives of 2'-modified siRNA...
  21. Masuya T, Murai M, Ito T, Aburaya S, Aoki W, Miyoshi H. Pinpoint Chemical Modification of the Quinone-Access Channel of Mitochondrial Complex I via a Two-Step Conjugation Reaction. Biochemistry. 2017;56:4279-4287 pubmed publisher
    ..a bulky ring-strained cycloalkyne possessing a rhodamine fluorophore directly reacts (via strain-promoted click chemistry) with the azido group incorporated (via ligand-directed tosyl chemistry) into Asp160 in the 49 kDa subunit of ..
  22. Dasari R, La Clair J, Kornienko A. Irreversible Protein Labeling by Paal-Knorr Conjugation. Chembiochem. 2017;18:1792-1796 pubmed publisher
    ..Although these are fundamental tools, there is a need for the discovery of reactions that can label native proteins. We report herein the adaptation of the Paal-Knorr reaction to label lysine residues in proteins via pyrrole linkages. ..
  23. Lee D, Kim T, Kim K, Ham J, Jang T, Kang K, et al. Evaluation of guggulsterone derivatives as novel kidney cell protective agents against cisplatin-induced nephrotoxicity. Bioorg Med Chem Lett. 2017;27:3156-3161 pubmed publisher
    Guggulsterone derivatives were prepared using [3+2] click chemistry with aryl and alkyl acetylene...
  24. Kalaoglu Altan O, Kirac Aydin A, Sümer Bolu B, Sanyal R, Sanyal A. Diels-Alder "Clickable" Biodegradable Nanofibers: Benign Tailoring of Scaffolds for Biomolecular Immobilization and Cell Growth. Bioconjug Chem. 2017;28:2420-2428 pubmed publisher
  25. Aziz Ali A, Gogoi D, Chaliha A, Buragohain A, Trivedi P, Saikia P, et al. Synthesis and biological evaluation of novel 1,2,3-triazole derivatives as anti-tubercular agents. Bioorg Med Chem Lett. 2017;27:3698-3703 pubmed publisher
    ..seventeen novel 1,2,3-triazole derivatives were efficiently synthesized in excellent yields by the popular 'click chemistry' approach and evaluated in vitro for their anti-tubercular activity against Mycobacterium tuberculosis H37Ra (..
  26. Patterson J, Gros E, Zhou H, Atassi G, Kerwin L, Carmody L, et al. Chemically generated IgG2 bispecific antibodies through disulfide bridging. Bioorg Med Chem Lett. 2017;27:3647-3652 pubmed publisher
    ..We report that an ?HER2/EGFR BsAb was successfully generated by this approach and retained the ability to bind both antigens with no significant loss of potency. ..
  27. Plass T, Milles S, Koehler C, Schultz C, Lemke E. Genetically encoded copper-free click chemistry. Angew Chem Int Ed Engl. 2011;50:3878-81 pubmed publisher
  28. Wang W, Zhu Y, Chen X. Selective Imaging of Gram-Negative and Gram-Positive Microbiotas in the Mouse Gut. Biochemistry. 2017;56:3889-3893 pubmed publisher
    ..This chemical method should be broadly applicable to different gut microbiota research fields and other bacterial communities studied in microbiology...
  29. Brabham R, Fascione M. Pyrrolysine Amber Stop-Codon Suppression: Development and Applications. Chembiochem. 2017;18:1973-1983 pubmed publisher
  30. Bjerknes M, Cheng H, McNitt C, Popik V. Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne-Azide Cycloaddition of Inorganic Azides. Bioconjug Chem. 2017;28:1560-1565 pubmed publisher
    ..The facile quenching of cyclooctynes demonstrated here should be useful in other bioorthogonal ligation techniques in which cyclooctynes are employed, including SPANC, Diels-Alder, and thiol-yne...
  31. Han Z, Chou C, Yang X, Bartlett M, Zheng Y. Profiling Cellular Substrates of Lysine Acetyltransferases GCN5 and p300 with Orthogonal Labeling and Click Chemistry. ACS Chem Biol. 2017;12:1547-1555 pubmed publisher
    ..These results demonstrate extensive engagement of GCN5 and p300 in cellular pathways and provide new insights into understanding their functions in specific biological processes. ..
  32. Paeth M, Stapleton J, Dougherty M, Fischesser H, Shepherd J, McCauley M, et al. Approaches for Conjugating Tailor-Made Polymers to Proteins. Methods Enzymol. 2017;590:193-224 pubmed publisher
    ..This reactive azide group can be conjugated to an alkyne-containing polymer using highly efficient click chemistry. These robust protocols can produce protein-polymer conjugates with various architectures and functionalities...
  33. Xie J, Bogliotti N. Synthesis and applications of carbohydrate-derived macrocyclic compounds. Chem Rev. 2014;114:7678-739 pubmed publisher
  34. Negwer I, Hirsch M, Kaloyanova S, Brown T, Peneva K, Butt H, et al. Modulation of Mitochondriotropic Properties of Cyanine Dyes by in Organello Copper-Free Click Reaction. Chembiochem. 2017;18:1814-1818 pubmed publisher
    ..This enhancement of a favorable property can be achieved by synthesis in organello, but not outside mitochondria. ..
  35. Martin F, Marconi D, Neamtu S, Radu T, Florescu M, Turcu R, et al. "Click" access to multilayer functionalized Au surface: A terpyridine patterning example. Mater Sci Eng C Mater Biol Appl. 2017;75:1343-1350 pubmed publisher
    ..DPN was used to direct pattern the terpyridine-ink on a pre-functionalized AuIDE electrode. The AFM topology resulted from DPN and PEIS demonstrated metal-coordinating ligand of Fe(II)-Terpy. ..
  36. Raddaoui N, Stazzoni S, Möckl L, Viverge B, Geiger F, Engelke H, et al. Dendrimer-Based Signal Amplification of Click-Labelled DNA in Situ. Chembiochem. 2017;18:1716-1720 pubmed publisher
  37. Isobe H, Fujino T. Triazole-linked analogues of DNA and RNA ((TL)DNA and (TL)RNA): synthesis and functions. Chem Rec. 2014;14:41-51 pubmed
    b>Click chemistry has provided us with access to DNA and RNA analogues with non-natural triazole internucleoside linkages...
  38. Rezki N, Aouad M. Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation. Acta Pharm. 2017;67:309-324 pubmed publisher
    ..Some of the designed 1,2,3-triazole conjugates 6a-o were recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains. ..
  39. Kosman J, Stanislawska A, Gluszynska A, Juskowiak B. Conjugation of hemin to G-quadruplex forming oligonucleotide using click chemistry. Int J Biol Macromol. 2017;101:799-804 pubmed publisher
    ..We report here the first attempt of conjugating hemin to the G-quadruplex DNA using click chemistry approach...
  40. Guttenplan A, Young L, Matak Vinkovic D, Kaminski C, Knowles T, Itzhaki L. Nanoscale click-reactive scaffolds from peptide self-assembly. J Nanobiotechnology. 2017;15:70 pubmed publisher
    ..Therefore, a general method is needed to conjugate proteins and other molecules to amyloid fibrils after the fibrils have self-assembled...
  41. Wu Y, Dong Y, Li J, Huang X, Cheng Y, Zhu C. A highly selective and sensitive polymer-based fluorescence sensor for Hg²?-ion detection via click reaction. Chem Asian J. 2011;6:2725-9 pubmed
  42. Rachel N, Toulouse J, Pelletier J. Transglutaminase-Catalyzed Bioconjugation Using One-Pot Metal-Free Bioorthogonal Chemistry. Bioconjug Chem. 2017;28:2518-2523 pubmed publisher
    ..Owing to the breadth of labels that MTG can use as a substrate, our results demonstrate the versatility of this system, with the researcher being able to combine specific protein substrates with a variety of labels...
  43. Sapsford K, Algar W, Berti L, Gemmill K, Casey B, Oh E, et al. Functionalizing nanoparticles with biological molecules: developing chemistries that facilitate nanotechnology. Chem Rev. 2013;113:1904-2074 pubmed publisher
  44. Elahipanah S, O Brien P, Rogozhnikov D, Yousaf M. General Dialdehyde Click Chemistry for Amine Bioconjugation. Bioconjug Chem. 2017;28:1422-1433 pubmed publisher
    ..We anticipate the broad utility of the general dialdehyde click chemistry to primary amines in all areas of chemical research, ranging from polymers and bioconjugation to material ..
  45. Sakin V, Hanne J, Dunder J, Anders Össwein M, Laketa V, Nikic I, et al. A Versatile Tool for Live-Cell Imaging and Super-Resolution Nanoscopy Studies of HIV-1 Env Distribution and Mobility. Cell Chem Biol. 2017;24:635-645.e5 pubmed publisher
    ..Introduction of a bio-orthogonal amino acid by genetic code expansion, combined with click chemistry, offers novel possibilities for site-specific, minimally invasive labeling...
  46. Richard E, Pifferi C, Fiore M, Samain E, Le Gouellec A, Fort S, et al. Chemobacterial Synthesis of a Sialyl-Tn Cyclopeptide Vaccine Candidate. Chembiochem. 2017;18:1730-1734 pubmed publisher
    ..several hundreds of milligrams, were then conjugated by using copper(I)-catalysed azide-alkyne cycloaddition click chemistry to a fully synthetic and immunogenic scaffold with the aim to create a candidate anticancer vaccine...
  47. Earla A, Braslau R. Covalently linked plasticizers: triazole analogues of phthalate plasticizers prepared by mild copper-free “click” reactions with azide-functionalized PVC. Macromol Rapid Commun. 2014;35:666-71 pubmed publisher
    Copper-free azide-alkyne click chemistry is utilized to covalently modify polyvinyl chloride(PVC)...