Bioorthogonal marking

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The bioorthogonal labeling includes biochemical methods for the molecular marker in which a selective chemical reaction takes place to disturb possible in a cell without the biological processes. Bioorthogonal labeling is a combination of metabolic labeling and a subsequent selective response used in vivo or in vitro . The bioorthogonal labeling enables in vivo signal molecules (reporter molecules) to be coupled to the molecule to be labeled which cannot be generated by cellular reactions, e.g. B. a synthetic fluorophore .

properties

Bioorthogonal labeling is based on the use of very selective chemical reactions in which few side reactions occur in order not to react with biomolecules . A non-specific reaction can inhibit cellular processes and reactions , which can lead to toxicity and would therefore be less suitable for use in vivo , e.g. B. in cell cultures . For this purpose, in the context of metabolic labeling , cell cultures are usually fed with a culture medium that contains labeled molecules with a specific functional group . These labeled molecules are converted by the metabolism or incorporated into other molecules. The functional group can then react further with a selective chemical reaction in the context of bioorthogonal labeling. In order to avoid rapid degradation of the label, the bond created in this way should also be resistant to the metabolism and have a sufficient reaction rate .

Various reactions of bioorthogonal labeling have been described, e.g. B. the 1,3-dipolar cycloaddition of azides and cyclooctynes ​​(synonymous with copper-free click chemistry ), or between nitrones and cyclooctynes, the formation of oximes or hydrazones from aldehydes or ketones , the tetrazine ligation, the isocyanide- based click reaction , the quadricyclane ligation, the Sonogashira coupling , the copper-catalyzed alkyne-azide cycloaddition , the Heck reaction , the cyclopropene-azide coupling, the myristylation , the cyanobenzothiazole condensation or the tetrazole-alkene cycloaddition. After biosynthesis, membrane proteins can be enzymatically coupled with azides, which in turn are coupled with reporter molecules via the Staudinger reaction.

application

With a bioorthogonal marking glycans , proteins , and lipids can be marked.

history

From the year 2000 bioorthogonal labeling was carried out using the Staudinger reaction of azides with triarylphosphines. The term 'bioorthogonal marking' was coined in 2003 by Carolyn Bertozzi .

Individual evidence

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  2. ↑ Jennifer A. Prescher, Danielle H. Dube, Carolyn R. Bertozzi: Chemical remodeling of cell surfaces in living animals . In: Nature . 430, No. 7002, 2004, pp. 873-877. doi : 10.1038 / nature02791 . PMID 15318217 .
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