New blue light-emitting isocyanobiphenyl based fluorophores: Their solvatochromic and biolabeling properties

Miklós Nagy, Dávid Rácz, Sándor Lajos Kovács, László Lázár, Péter Pál Fehér, Mihály Purgel, M. Zsuga, S. Kéki

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Abstract

The preparation and optical study of 4-amino-4′-isocyanobiphenyl (ICAB) and its mono-and dialkylated derivatives (monoMICAB and diMICAB) are reported. They were found to be effective blue light emitters with a solvatochromic range of Δλmax = 104 nm, 92 nm and 90 nm, respectively. All three compounds turned out to be promising candidates in protein-labeling, yielding ∼70-190× increase in their fluorescence intensity when mixed with 10× molar excess of bovine serum albumin (BSA). The binding constants for the BSA-fluorophore complexes were found to be KICAB-BSA = 3.8 × 104 ± 5.7 × 103 M-1, KmonoMICAB-BSA = 6.0 × 104 ± 3.9 × 103 M-1 and KdiMICAB-BSA = 2.3 × 104 ± 3.2 × 103 M-1. Time resolved fluorescence measurements revealed a nearly uniform ∼2 ns lifetime for all three BSA-complexed ICAB derivatives.

Original languageEnglish
Pages (from-to)124-134
Number of pages11
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume318
DOIs
Publication statusPublished - Mar 1 2016

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Keywords

  • BSA
  • DFT
  • Fluorescence
  • Isocyanobiphenyl
  • Solvatochromism

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

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