Click chemistry bioconjugation

Gopin A, Ebner S, Attali B, Shabat D. Enzymatic activation of second-generation dendritic prodrugs Conjugation of self-immolative dendrimers with poly(ethylene glycol) via click chemistry. Bioconjugate Chem 2006 17 1432-1440. 

Hong V, Steinmetz NF, Manchester M, Finn MG (2010) Labeling live cells by copper-catalyzed alkyne-azide click chemistry. Bioconjug Chem 21 1912 1916... 

Jolck RL Berg RH, Andresen TL (2010) Solid-phase synthesis of PEGylated lipopeptides using click chemistry. Bioconjugate Chem 21 807-810... 

Hiki S, Kataoka K (2010) Versatile and selective synthesis of click chemistry compatible heterobifunctional poly(ethylene glycol)s possessing azide and alkyne functionalities. Bioconjug Chem 21 248-254... 

Click chemistry refers to the reaction between an azido functional group and an alkyne to form a [3 + 2] cycloaddition product, a 5-membered triazole ring. This reaction has been used for many years in organic synthesis to form heterocyclic rings. Normally, the click reaction requires high temperatures, and this was the main reason that it was not used as a bioconjugation tool. However, it was discovered that in aqueous solutions and in the presence of Cu(I), the reaction kinetics are dramatically accelerated to provide high yields even at room temperature and ambient pressures (Rostovtsev et al., 2002 Tornoe et al., 2002 Sharpless et al., 2005). 

Bonnet, D., Ilien, B., Galzi, J.-L., Riche, S., Antheaune, C., and Hibert, M. (2006) A rapid and versatile method to label receptor ligands using click chemistry Validation with the muscarinic Ml antagonist pirenzepine. Bioconjugate Chem. 17, 1618-1623. 

Lutz, J.F., Borner, H.G., and Weichenhan, K. "Combining ATRP and click chemistry a promising platform toward functional biocompatible polymers and polymer bioconjugates". Macromolecules 39(19), 6376-6383 (2006). 

Key words Liposome, Azide-alkyne cycloaddition, Bioconjugation chemistry. Click chemistry. 

Lutz JF, Zarafshani Z (2008) Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne click chemistry. Adv Drug Deliv Rev 60 958-970... 

Synthesis of triazoles and tetrazoles by 1,3-dipolar cycloaddition ( click chemistry ) in bioconjugate chemistry 06CJ01640. 

M. van Dijk, D.T. Rijkers, R.M. Liskamp, C.F. van Nostmm, W.E. Hennink, Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies. Bioconjug. Chem. 20, 2001-2016 (2009)... 

FIGURE 3.34 Examples of reactions of click chemistry used in bioconjugation... 

Li, M., et al. 2008. Responsive polymer-protein bioconjugates prepared by RAFT polymerization and copper-catalyzed azide-alkyne click chemistry. Macromolecular Rapid Communications 29(12-13) 1172-1176. 

McKay CS, Einn MG (2014) Click chemistry in complex nuxtures bioorthogonal bioconjugation. Chem Biol 21(9) 1075-1101. doi 10.1016/j.chembiol.2014.09.002... 

Marks IS, Kang JS, Jones BT, Landmark KJ, Cleland AJ, Taton TA (2011) Strain-promoted click chemistry for terminal labeling of DNA. Bioconjug Chem 22(7) 1259-1263. doi 10.1021/ bcl003668... 

Xiong H, Leonard P, Seela F (2012) Construction and assembly of branched Y-shaped DNA click chemistry performed on dendronized 8-aza-7-deazaguanine oUgonucleotides. Bioconjug Chem 23(4) 856-870. doi 10.1021/bc300013k... 

Jiang X, Lok MC, Hennink WE (2007) Degradable-brushed pHEMA-pDMAEMA synthesized via ATRP and click chemistry for gene delivtay. Bioconjug Chem 18 2077—2084... 

C.S. McKay, M.G. Finn, Click chemistry in complex mixtures bioorthogonal bioconjugation, Chem. Biol. 21 (September 18, 2014) 1075-1101. 

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