Squaraine rotaxanes are intensely colored and highly fluorescent dyes with deep-red absorption/emission wavelengths. We have subsequently shown that squaraine rotaxanes can be employed as targeted fluorescent molecular probes for cell microscopy and whole-body imaging of disease models in small living animals. To date, most of the squaraine rotaxane probes have been lipophilic or partially water soluble compounds. However, there is a need for squaraine rotaxanes that are highly water soluble. Eight squaraine rotaxanes were prepared and assessed for chemical stability and suitability as water soluble, fluorescent tracers. The most stable squaraine rotaxanes have four large stopper groups attached to the ends of the encapsulated squaraine, and two members of this structural class have promise as highly fluorescent tracers with rapid renal clearance and very low tissue uptake in living mice.

Water soluble, deep-red fluorescent squaraine rotaxanes

243rd National Meeting (2012)

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