PMID- 31160696 OWN - NLM STAT- PubMed-not-MEDLINE DCOM- 20200408 LR - 20210109 IS - 2045-2322 (Electronic) IS - 2045-2322 (Linking) VI - 9 IP - 1 DP - 2019 Jun 3 TI - Amino-isocyanoacridines: Novel, Tunable Solvatochromic Fluorophores as Physiological pH Probes. PG - 8250 LID - 10.1038/s41598-019-44760-9 [doi] LID - 8250 AB - 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 (Phi(F) = 2.9-0.4%) in water, reduced basicity (pK(a) = 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. FAU - Nagy, Miklos AU - Nagy M AD - Department of Applied Chemistry, University of Debrecen, 4010, Debrecen, Hungary. FAU - Racz, David AU - Racz D AD - Department of Applied Chemistry, University of Debrecen, 4010, Debrecen, Hungary. FAU - Nagy, Zsolt Laszlo AU - Nagy ZL AD - Department of Applied Chemistry, University of Debrecen, 4010, Debrecen, Hungary. FAU - Feher, Peter Pal AU - Feher PP AD - Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117 Budapest, Magyar tudosok korutja 2, Budapest, Hungary. FAU - Kovacs, Sandor Lajos AU - Kovacs SL AD - Department of Applied Chemistry, University of Debrecen, 4010, Debrecen, Hungary. FAU - Banko, Csaba AU - Banko C AD - University of Debrecen, Medical and Health Science Center, Faculty of Medicine, Department of Biophysics and Cell Biology, 4010, Debrecen, Hungary. FAU - Bacso, Zsolt AU - Bacso Z AD - University of Debrecen, Medical and Health Science Center, Faculty of Medicine, Department of Biophysics and Cell Biology, 4010, Debrecen, Hungary. FAU - Kiss, Alexandra AU - Kiss A AD - Department of Biotechnology and Microbiology, Faculty of Science, University of Debrecen, Debrecen, 4010, Hungary. FAU - Zsuga, Miklos AU - Zsuga M AD - Department of Applied Chemistry, University of Debrecen, 4010, Debrecen, Hungary. FAU - Keki, Sandor AU - Keki S AD - Department of Applied Chemistry, University of Debrecen, 4010, Debrecen, Hungary. keki.sandor@science.unideb.hu. LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20190603 PL - England TA - Sci Rep JT - Scientific reports JID - 101563288 SB - IM PMC - PMC6547668 COIS- The authors declare no competing interests. EDAT- 2019/06/05 06:00 MHDA- 2019/06/05 06:01 PMCR- 2019/06/03 CRDT- 2019/06/05 06:00 PHST- 2018/12/06 00:00 [received] PHST- 2019/05/23 00:00 [accepted] PHST- 2019/06/05 06:00 [entrez] PHST- 2019/06/05 06:00 [pubmed] PHST- 2019/06/05 06:01 [medline] PHST- 2019/06/03 00:00 [pmc-release] AID - 10.1038/s41598-019-44760-9 [pii] AID - 44760 [pii] AID - 10.1038/s41598-019-44760-9 [doi] PST - epublish SO - Sci Rep. 2019 Jun 3;9(1):8250. doi: 10.1038/s41598-019-44760-9.