Amino-isocyanoacridines: Novel, Tunable Solvatochromic Fluorophores as Physiological pH Probes

Miklós Nagy, Dávid Rácz, Zsolt László Nagy, Péter Pál Fehér, Sándor Lajos Kovács, Csaba Bankó, Z. Bacsó, Alexandra Kiss, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

Abstract

Amino-isocyanoacridines (ICAAcs), as first members of their class, turned out to be a novel, multifunctional acridine orange (AO) type dye family with a number of additional favorable properties. They have enhanced solvatochromic emission range, low quantum yields (ΦF = 2.9–0.4%) in water, reduced basicity (pKa = 7.05–7.58), and their optical behavior could be fine-tuned by complexation with Ag(I) ions, too. Based on both their vibronic absorption and the charge transfer bands, ICAAcs can be applied as stable pH-probes with great precision (2–3% error) in the physiological pH range of 6–8 using UV-vis and fluorescence detection. The dyes are also able to sense pH change in different microenvironments, such as the Stern layer, as it was demonstrated on sodium lauryl sulfate micelles. The optical behavior of the ICAAc derivatives is discussed based on high-level quantum chemical calculations. All three dyes are well-applicable with conventional epifluorescence imaging. Furthermore, at the blue excitation, diMICAAc is optimally suited as a whole-cell probe for both the conventional microscopic and the laser-illumination studies, like flow- and imaging cytometric, or confocal laser-scanning microscopic examinations.

Original languageEnglish
Article number8250
JournalScientific reports
Volume9
Issue number1
DOIs
Publication statusPublished - Dec 1 2019

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Coloring Agents
Lasers
Acridine Orange
Micelles
Lighting
Sodium Dodecyl Sulfate
Fluorescence
Ions
Water

ASJC Scopus subject areas

  • General

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Amino-isocyanoacridines : Novel, Tunable Solvatochromic Fluorophores as Physiological pH Probes. / Nagy, Miklós; Rácz, Dávid; Nagy, Zsolt László; Fehér, Péter Pál; Kovács, Sándor Lajos; Bankó, Csaba; Bacsó, Z.; Kiss, Alexandra; Zsuga, M.; Kéki, S.

In: Scientific reports, Vol. 9, No. 1, 8250, 01.12.2019.

Research output: Contribution to journalArticle

Nagy, Miklós ; Rácz, Dávid ; Nagy, Zsolt László ; Fehér, Péter Pál ; Kovács, Sándor Lajos ; Bankó, Csaba ; Bacsó, Z. ; Kiss, Alexandra ; Zsuga, M. ; Kéki, S. / Amino-isocyanoacridines : Novel, Tunable Solvatochromic Fluorophores as Physiological pH Probes. In: Scientific reports. 2019 ; Vol. 9, No. 1.
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