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These complexes were very weakly emissive owing to rapid C=N isomerization of the nitrone moiety, but exhibited significant emission enhancement upon strain\u2010promoted alkyne\u2013nitrone cycloaddition (SPANC) reaction with bicyclo[6.1.0]nonyne (BCN)\u2010modified substrates. The modification of nitrone with a dicationic ruthenium(II) polypyridine unit at the \u03b1\u2010<jats:italic>C<\/jats:italic>\u2010position and a phenyl ring at the <jats:italic>N<\/jats:italic>\u2010position led to remarkably accelerated reaction kinetics, which are substantially greater (up to \u2248278 fold) than those of other acyclic nitrone\u2013BCN systems. Interestingly, the complexes achieved specific cell membrane\/cytosol staining upon specific labeling of an exogenous substrate, BCN\u2010modified decane (BCN\u2010C10), in live cells. Importantly, the in situ generation of the more lipophilic isoxazoline adduct in the cytoplasm resulted in increased cytotoxicity, highlighting a novel approach to apply the SPANC labeling technique in drug activation.<\/jats:p>","DOI":"10.1002\/chem.201601332","type":"journal-article","created":{"date-parts":[[2016,6,7]],"date-time":"2016-06-07T07:01:52Z","timestamp":1465282912000},"page":"9649-9659","source":"Crossref","is-referenced-by-count":31,"title":["Structural Manipulation of Ruthenium(II) Polypyridine Nitrone Complexes to Generate Phosphorogenic Bioorthogonal Reagents for Selective Cellular Labeling"],"prefix":"10.1002","volume":"22","author":[{"given":"Tommy Siu\u2010Ming","family":"Tang","sequence":"first","affiliation":[{"name":"Department of Biology and Chemistry City University of Hong Kong  Tat Chee Avenue, Kowloon Hong Kong P.R. 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