Fast and simple access to N-arylated 3-hydroxyquinolin-4(1H)-ones starting from easily available 1-methyl-2-iodoterephthalate and variously substituted anilines is presented. N-Alkylated anthranilic acid derivatives represent important intermediates. They can be advantageously prepared by solid-phase synthesis, by Buchwald-Hartwig amination or reductive amination with wide substrate scope and with excellent crude purities.

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The glutathione cleavable conjugates of amino-BODIPY dye with model drugs have been tested for monitoring the drug release via ratiometric fluorescence based on two excitation and one emission wavelength. As a self-immolative linker was used for the construction of conjugates, free amino-BODIPY was released with the drug. Different excitation profiles of the dye before and after conjugate cleavage and similar emission wavelengths that enabled monitoring the release of the drug via the OFF-ON effect were successfully tested inside the cancer cells. UV/Vis spectrometry could be used in the quantification of the conjugate/drug in an analyte irrespective of the cleavage grade. As the system functionality was based only on the altered acylamino-BODIPY present in the conjugate to amino-BODIPY released during the cleavage, the method could be applied as a ratiometric fluorescence theranostic system to other non-fluorescent drugs. Moreover, the present conjugates demonstrated their potential application in molecular electronics as a "power supply" selector enabling the application of two power sources for one "bulb" to maintain its light intensity.

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