New quinolone-based thiol-reactive lanthanide luminescent probes

Luminescent lanthanide ion complexes are distinguished by unique light emitting properties that enable both highly sensitive detection of lanthanide labels attached to biomolecules and contrast imaging of various micro objects (cells, nanoparticles, etc.). Previously, we synthesized amine-reactive cs124-based luminescent lanthanide chelates with improved brightness and metal retention. Here we report the synthesis of new thiol-reactive derivatives of the same compounds including bromoacetamido-, and maleimido-forms of cs124 and cs124CF3 fluorophores. Maleimido-compounds displayed exceptional reactivity instantaneously coupling to thiols at physiological conditions at micromolar probes concentrations. Surprisingly, they displayed strong quenching by adjacent maleimido-group, which was completely eliminated after reaction with thiols, thereby enabling their simple detection by monitoring the light emission of the reaction mixture. This reaction can be used for hyper-sensitive determination of biologically important sulphydryl compounds (e.g. glutathione, co-enzyme A, etc.) in time-resolved mode.

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► Thiol-reactive maleimide and bromoacetamide Eu3+ and Tb3+ chelates were synthesized.
► The maleimide chelates possessed exceptionally high reactivity towards thiols.
► Tb3+ maleimide chelates were quenched but lightened after reaction with thiols.
► This effect can be used for hyper-sensitive thiol detection in time-resolved mode.