Amino acid recognition by fine tuning the association constants: Tailored naphthalimides in pillar[5]arene-based indicator displacement assays

Bojtár, Márton Gáspár and Paudics, Adrien and Hessz, Dóra and Kubinyi, Miklós and Bitter, István (2016) Amino acid recognition by fine tuning the association constants: Tailored naphthalimides in pillar[5]arene-based indicator displacement assays. RSC Advances, 6. pp. 86269-86275. ISSN 2046-2069

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Abstract

Three aminonaphthalimide derivatives were synthesized bearing different anchoring groups in their 4-position in order to adjust the supramolecular interactions with carboxylato-pillar[5]arene (WP5), an anionic, water-soluble host. The modification of the anchor groups resulted in varying association constants embracing three orders of magnitude (Ka from ∼103 to ∼106) in buffered water. Since the fluorophore responded significantly to the electronic environment, large fluorescence quenching was observed with the anionic WP5 host. The naphthalimide indicator-WP5 supramolecular assemblies were used to detect arginine and lysine with complete selectivity over other non-basic α-amino acids by turn-on fluorescence. The same assemblies proved to be highly sensitive fluorescence displacement assays for the detection of cadaverine

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