Xanthene dyes (fluoresceins, rhodamines and rhodols) containing linkers for bio-conjugation are used extensively as fluorescent labels and probes to study biological systems. The classic synthesis of functionalized xanthenes from trimellitic anhydride produces symmetrical dyes possessing a reactive carboxyl group suitable for bio-conjugation.  However, this method also produces a mixture of 5- and 6-carboxy substituted regioisomers which are difficult to separate and makes spectroscopic characterization problematic.<br/>      We have found that the need of a “reactive carboxyl” is unnecessary for conjugation.  Activation of simple 2-carboxyl containing rhodamine dyes derived from symmetrical phthalic anhydride proceeds under unexpectedly mild reaction conditions. We have synthesized unsymmetrical, single isomer, bright, photo-stable rhodamine dyes and evaluated their use in immunoassays and in super-resolution imaging. The asymmetric nature of the dye also allowed us to introduce two chemically orthogonal functional groups into the rhodamine dye system. We have also demonstrated the use of a bi-functional rhodamine system as a linker.<br/>

Synthesis and evaluation of unsymmetrical single-isomer rhodamine dyes for use in immunoassays and super-resolution imaging

251st National Meeting (2016)

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