4.7 Article

Bio-additive-based screening: toward evaluation of the biocompatibility of chemical reactions

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NATURE PROTOCOLS
卷 14, 期 9, 页码 2599-2626

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NATURE PUBLISHING GROUP
DOI: 10.1038/s41596-019-0190-2

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  1. Deutsche Forschungsgemeinschaft [RE2796/6-1]
  2. Fonds der Chemischen Industrie

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A requirement for biochemical labeling strategies is a pronounced biocompatibility of the underlying reaction methodology. This protocol enables a systematic evaluation of the biocompatibility of (new) reaction methodologies that are potentially attractive for biochemical applications. The cellular environment for in vitro and in vivo applications is mimicked by the one-by-one addition of diverse bio-additives to the reaction. The influence of the bio-additives on the product yield, termed bio-robustness, is quantified by gas chromatography (GC) or NMR techniques, whereas qualitative analysis of the level of biomolecule preservation by ultra-HPLC-mass spectrometry (UHPLC-MS) or gel electrophoresis enables monitoring of the effects of the reaction conditions on the biomolecule stability, e.g., bio-additive modification or degradation. The 22 chosen bio-additives and the required controls can be completely evaluated within 5-7 working days, depending on reaction time, instrument and the general equipment availability of the lab. We illustrate this protocol by assessing the reaction biocompatibility of a copper-catalyzed N-arylation of sulfonamides. The hereby obtained results are compared to those for a reaction that is characterized by high reaction biocompatibility: the energy-transfer-enabled disulfide-ene reaction.

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