Click bioconjugations

Figure 14.4. Surface functionalization and bioconjugation methods developed for GNRs (a) electrostatic physisorption onto PE-coated GNRs (b) covalent attachment via carbodiimide coupling (c) "click" bioconjugation (d) chemisorption using thiols (e) chemisorption using dithiocarbamates (DTCs).

Bemdl S, Herzig N, Kele P et al (2009) Comparison of a nucleosidic vs non-nucleosidic postsynthetic click modification of DNA with base-labile fluorescent probes. Bioconjug... 

Hiki S, Kataoka K (2007) A facile synthesis of azido-terminated heterobifunctional poly (ethylene glycol)s for click conjugation. Bioconjug Chem 18 2191-2196... 

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). 

The advantage of the click reaction for bioconjugation is that the reactant pair is not reactive with any other functional group encountered in biological systems. This property of... 

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... 

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. 

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

Bundy, B.C. and Swartz, J.R. (2010) Site-specific incorporation of p-propargyloxyphenylalanine in a cell-free environment for direct protein—protein click conjugation. Bioconjugate Chem., 21, 255-263. 

POC-click is formed by thermo-cross-linking the mixture of pre-POC-N (azide-containing POC prepolymer) and pre-POC-Al (alkyne-containing POC prepolymer) the process applies synchronous binary cross-link mechanism, esterification, and thermal click reaction, and the residual azide groups on the surface of POC-click film or scaffold paved the way of surface bioconjugation through strain-promoted alkyne-azide cycloaddition (SPAAC), another copper-free click reaction. 

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... 

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