Aminonaphthalimide-based dipodal imidazolium/triazole receptors for fluorescent sensing of nucleoside polyphosphates

János B. Czirok, Márton Bojtár, Dóra Hessz, P. Baranyai, L. Drahos, M. Kubinyi, I. Bitter

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Novel aminonaphthalimide-based two-armed imidazolium/triazole receptors were synthesized to compare their fluorescent responses towards nucleoside polyphosphates with those of three-armed podands described recently. Our two constitutional isomer ligands comprised one imidazolium and an additional 1,2,3-triazole moiety in the binding site exhibited 'turn-on' fluorescence enhancements in HEPES buffer (pH 7.5) upon addition of ATP, GTP and UTP. The sensitivity of sensing was found to strongly depend on the order of heterocyclic subunits in the arms, when the imidazolium group was displaced to the vicinity of the naphthalimide marker significantly higher sensitivity was achieved. In aqueous solutions, however, the association constants were considered to be unreliable due to the occurrence of some colloidal precipitate (unvisible to the naked eye) that could be detected only by light scattering. The spectroscopic measurements repeated in HEPES-acetonitrile mixed solvent affording stable solutions gave association constants log K = 6.3-6.5 for ATP, GTP and UTP alike (1:2 ligand-triphosphate stoichiometry) retaining the selectivity over di-and monophosphates.

Original languageEnglish
Pages (from-to)280-287
Number of pages8
JournalSensors and Actuators, B: Chemical
Volume182
DOIs
Publication statusPublished - 2013

Fingerprint

HEPES
Polyphosphates
Uridine Triphosphate
nucleosides
Triazoles
adenosine triphosphate
Adenosinetriphosphate
Guanosine Triphosphate
Nucleosides
Naphthalimides
Adenosine Triphosphate
Ligands
Association reactions
ligands
sensitivity
Binding sites
retaining
Acetonitrile
Stoichiometry
Isomers

Keywords

  • ATP, GTP, UTP sensing
  • Click chemistry
  • Fluorescent sensor
  • Naphthalimide fluorophore
  • Nucleoside polyphosphates

ASJC Scopus subject areas

  • Instrumentation
  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Electrical and Electronic Engineering

Cite this

Aminonaphthalimide-based dipodal imidazolium/triazole receptors for fluorescent sensing of nucleoside polyphosphates. / Czirok, János B.; Bojtár, Márton; Hessz, Dóra; Baranyai, P.; Drahos, L.; Kubinyi, M.; Bitter, I.

In: Sensors and Actuators, B: Chemical, Vol. 182, 2013, p. 280-287.

Research output: Contribution to journalArticle

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