Literature DB >> 19538051

Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research.

Kido Nwe1, Martin W Brechbiel.   

Abstract

This update summarizes the growing application of "click" chemistry in diverse areas such as bioconjugation, drug discovery, materials science, and radiochemistry. This update also discusses click chemistry reactions that proceed rapidly with high selectivity, specificity, and yield. Two important characteristics make click chemistry so attractive for assembling compounds, reagents, and biomolecules for preclinical and clinical applications. First, click reactions are bio-orthogonal; neither the reactants nor their product's functional groups interact with functionalized biomolecules. Second, the reactions proceed with ease under mild nontoxic conditions, such as at room temperature and, usually, in water. The copper-catalyzed Huisgen cycloaddition, azide-alkyne [3 + 2] dipolar cycloaddition, Staudinger ligation, and azide-phosphine ligation each possess these unique qualities. These reactions can be used to modify one cellular component while leaving others unharmed or untouched. Click chemistry has found increasing applications in all aspects of drug discovery in medicinal chemistry, such as for generating lead compounds through combinatorial methods. Bioconjugation via click chemistry is rigorously employed in proteomics and nucleic research. In radiochemistry, selective radiolabeling of biomolecules in cells and living organisms for imaging and therapy has been realized by this technology. Bifunctional chelating agents for several radionuclides useful for positron emission tomography and single-photon emission computed tomography imaging have also been prepared by using click chemistry. This review concludes that click chemistry is not the perfect conjugation and assembly technology for all applications, but provides a powerful, attractive alternative to conventional chemistry. This chemistry has proven itself to be superior in satisfying many criteria (e.g., biocompatibility, selectivity, yield, stereospecificity, and so forth); thus, one can expect it will consequently become a more routine strategy in the near future for a wide range of applications.

Entities:  

Mesh:

Year:  2009        PMID: 19538051      PMCID: PMC2811415          DOI: 10.1089/cbr.2008.0626

Source DB:  PubMed          Journal:  Cancer Biother Radiopharm        ISSN: 1084-9785            Impact factor:   3.099


  68 in total

1.  Inhibitors of HIV-1 protease by using in situ click chemistry.

Authors:  Matthew Whiting; John Muldoon; Ying-Chuan Lin; Steven M Silverman; William Lindstrom; Arthur J Olson; Hartmuth C Kolb; M G Finn; K Barry Sharpless; John H Elder; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-20       Impact factor: 15.336

Review 2.  Chemistry in living systems.

Authors:  Jennifer A Prescher; Carolyn R Bertozzi
Journal:  Nat Chem Biol       Date:  2005-06       Impact factor: 15.040

Review 3.  Transition metal catalyzed methods for site-selective protein modification.

Authors:  John M Antos; Matthew B Francis
Journal:  Curr Opin Chem Biol       Date:  2006-05-12       Impact factor: 8.822

4.  "Click to chelate": synthesis and installation of metal chelates into biomolecules in a single step.

Authors:  Thomas L Mindt; Harriet Struthers; Luc Brans; Todor Anguelov; Christian Schweinsberg; Veronique Maes; Dirk Tourwé; Roger Schibli
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

Review 5.  Novel strategies for the site-specific covalent labelling of nucleic acids.

Authors:  Samuel H Weisbrod; Andreas Marx
Journal:  Chem Commun (Camb)       Date:  2008-09-25       Impact factor: 6.222

6.  In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors.

Authors:  J H Condra; W A Schleif; O M Blahy; L J Gabryelski; D J Graham; J C Quintero; A Rhodes; H L Robbins; E Roth; M Shivaprakash
Journal:  Nature       Date:  1995-04-06       Impact factor: 49.962

7.  In vivo tumor cell targeting with "click" nanoparticles.

Authors:  Geoffrey von Maltzahn; Yin Ren; Ji-Ho Park; Dal-Hee Min; Venkata Ramana Kotamraju; Jayanthi Jayakumar; Valentina Fogal; Michael J Sailor; Erkki Ruoslahti; Sangeeta N Bhatia
Journal:  Bioconjug Chem       Date:  2008-07-09       Impact factor: 4.774

8.  Design, synthesis and structure-activity relationships of azole acids as novel, potent dual PPAR alpha/gamma agonists.

Authors:  Hao Zhang; Denis E Ryono; Pratik Devasthale; Wei Wang; Kevin O'Malley; Dennis Farrelly; Liqun Gu; Thomas Harrity; Michael Cap; Cuixia Chu; Kenneth Locke; Litao Zhang; Jonathan Lippy; Lori Kunselman; Nathan Morgan; Neil Flynn; Lisa Moore; Vinayak Hosagrahara; Lisa Zhang; Pathanjali Kadiyala; Carrie Xu; Arthur M Doweyko; Aneka Bell; Chiehying Chang; Jodi Muckelbauer; Robert Zahler; Narayanan Hariharan; Peter T W Cheng
Journal:  Bioorg Med Chem Lett       Date:  2009-01-15       Impact factor: 2.823

9.  Synthesis of novel 1,4,7,10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds.

Authors:  Sebastian Knör; Armin Modlinger; Thorsten Poethko; Margret Schottelius; Hans-Jürgen Wester; Horst Kessler
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

10.  A versatile method for the preparation of conjugates of peptides with DNA/PNA/analog by employing chemo-selective click reaction in water.

Authors:  Khirud Gogoi; Meenakshi V Mane; Sunita S Kunte; Vaijayanti A Kumar
Journal:  Nucleic Acids Res       Date:  2007-11-02       Impact factor: 16.971

View more
  63 in total

Review 1.  Inorganic Complexes and Metal-Based Nanomaterials for Infectious Disease Diagnostics.

Authors:  Christine F Markwalter; Andrew G Kantor; Carson P Moore; Kelly A Richardson; David W Wright
Journal:  Chem Rev       Date:  2018-12-04       Impact factor: 60.622

2.  Water-Soluble Palladium Reagents for Cysteine S-Arylation under Ambient Aqueous Conditions.

Authors:  Anthony J Rojas; Bradley L Pentelute; Stephen L Buchwald
Journal:  Org Lett       Date:  2017-08-04       Impact factor: 6.005

3.  A modular, plasmin-sensitive, clickable poly(ethylene glycol)-heparin-laminin microsphere system for establishing growth factor gradients in nerve guidance conduits.

Authors:  Jacob L Roam; Ying Yan; Peter K Nguyen; Ian S Kinstlinger; Michael K Leuchter; Daniel A Hunter; Matthew D Wood; Donald L Elbert
Journal:  Biomaterials       Date:  2015-08-31       Impact factor: 12.479

Review 4.  Protein-Engineered Functional Materials.

Authors:  Yao Wang; Priya Katyal; Jin Kim Montclare
Journal:  Adv Healthc Mater       Date:  2019-04-02       Impact factor: 9.933

Review 5.  18 F-Labeling of Sensitive Biomolecules for Positron Emission Tomography.

Authors:  Hema S Krishnan; Longle Ma; Neil Vasdev; Steven H Liang
Journal:  Chemistry       Date:  2017-09-01       Impact factor: 5.236

Review 6.  Click Chemistry in the Development of Contrast Agents for Magnetic Resonance Imaging.

Authors:  Sudath Hapuarachchige; Dmitri Artemov
Journal:  Top Magn Reson Imaging       Date:  2016-10

7.  A practical guide to the construction of radiometallated bioconjugates for positron emission tomography.

Authors:  Brian M Zeglis; Jason S Lewis
Journal:  Dalton Trans       Date:  2011-03-25       Impact factor: 4.390

8.  Synthesis of novel (-)-epicatechin derivatives as potential endothelial GPER agonists: Evaluation of biological effects.

Authors:  Viviana Sarmiento; Israel Ramirez-Sanchez; Aldo Moreno-Ulloa; Diego Romero-Perez; Daniel Chávez; Miguel Ortiz; Nayelli Najera; Jose Correa-Basurto; Francisco Villarreal; Guillermo Ceballos
Journal:  Bioorg Med Chem Lett       Date:  2018-01-24       Impact factor: 2.823

9.  Design, Synthesis, and Evaluation of Novel 3-Carboranyl-1,8-Naphthalimide Derivatives as Potential Anticancer Agents.

Authors:  Sebastian Rykowski; Dorota Gurda-Woźna; Marta Orlicka-Płocka; Agnieszka Fedoruk-Wyszomirska; Małgorzata Giel-Pietraszuk; Eliza Wyszko; Aleksandra Kowalczyk; Paweł Stączek; Andrzej Bak; Agnieszka Kiliszek; Wojciech Rypniewski; Agnieszka B Olejniczak
Journal:  Int J Mol Sci       Date:  2021-03-09       Impact factor: 5.923

10.  Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.

Authors:  Alexander B Draganov; Ke Wang; Jalisa Holmes; Krishna Damera; Danzhu Wang; Chaofeng Dai; Binghe Wang
Journal:  Chem Commun (Camb)       Date:  2015-10-21       Impact factor: 6.222

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.