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

Márton Bojtár, Adrien Paudics, Dóra Hessz, Miklós Kubinyi, István Bitter

Research output: Contribution to journalArticle

15 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)86269-86275
Number of pages7
JournalRSC Advances
Volume6
Issue number89
DOIs
Publication statusPublished - Jan 1 2016

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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