TY - JOUR
T1 - New quinolone-based thiol-reactive lanthanide luminescent probes
AU - Wirpsza, Laura
AU - Krasnoperov, Lev
AU - Mustaev, Arkady
N1 - Funding Information:
This study was supported by NIH grant RO1 GM-307-17-21 to A.M.
PY - 2013/2/1
Y1 - 2013/2/1
N2 - 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.
AB - 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.
KW - Detection
KW - Labeling
KW - Lanthanide
KW - Luminescence
KW - Reactive
KW - Thiol
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U2 - 10.1016/j.jphotochem.2012.12.008
DO - 10.1016/j.jphotochem.2012.12.008
M3 - Article
AN - SCOPUS:84872140330
SN - 1010-6030
VL - 253
SP - 30
EP - 37
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
ER -