A naphthalimide-tyrosine-based dicationic amphiphile for intracellular ‘turn-on’ simultaneous detection of ATP and CTP

Abstract

We have developed a new naphthalimide-based amphiphile (YN-1) for the simultaneous detection of ATP and CTP. In YN-1, the cationic tyrosine-linked polyamine (+2 charge, hydrophilic unit) is appended at the -peri position of naphthalimide (hydrophobic unit). YN-1 and its Boc-protected compound 4 were characterized using state-of-the-art spectroscopic and optical techniques such as NMR, IR, UV-vis and fluorescence. The fluorescence data revealed that YN-1 showed a ‘turn-on’ (λ_em = 440 nm) fluorescence response for nanomolar detection of nucleoside triphosphates such as ATP and CTP in 20% HEPES buffer-DMSO solution. YN-1 also showed a concentration-based discrimination between ATP and CTP. YN-1 has been successfully applied for bioimaging of nucleoside triphosphates in MCF-7 live cancer cells with good compatibility. Therefore, the important findings from the present work will provide insight for future development of fluorescent probes to detect various kinds of essential nucleoside triphosphates.