Dataset Information

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

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.

SUBMITTER: Nagy M

PROVIDER: S-EPMC6547668 | biostudies-other | 2019 Jun

REPOSITORIES: biostudies-other

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Publications

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

Nagy Miklós M Rácz Dávid D Nagy Zsolt László ZL Fehér Péter Pál PP Kovács Sándor Lajos SL Bankó Csaba C Bacsó Zsolt Z Kiss Alexandra A Zsuga Miklós M Kéki Sándor S

Scientific reports 20190603 1

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 (Φ<sub>F</sub> = 2.9-0.4%) in water, reduced basicity (pK<sub>a</sub> = 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 ba ...[more]

PMID: 31160696

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Project description:Proper three-dimensional structures are essential for maintaining the functionality of proteins and for avoiding pathological consequences of improper folding. Misfolding and aggregation of proteins have been both associated with neurodegenerative disease. Therefore, a variety of fluorogenic tools that respond to both polarity and viscosity have been developed to detect protein aggregation. However, the rational design of highly sensitive fluorophores that respond solely to polarity has remained elusive. In this work, we demonstrate that electron-withdrawing heteroatoms with (d-p)-π* conjugation can stabilize lowest unoccupied molecular orbital (LUMO) energy levels and promote bathochromic shifts. Guided by computational analyses, we have devised a novel series of xanthone-based solvatochromic fluorophores that have rarely been systematically studied. The resulting probes exhibit superior sensitivity to polarity but are insensitive to viscosity. As proof of concept, we have synthesized protein targeting probes for live-cell confocal imaging intended to quantify the polarity of misfolded and aggregated proteins. Interestingly, our results reveal several layers of protein aggregates in a way that we had not anticipated. First, microenvironments with reduced polarity were validated in the misfolding and aggregation of folded globular proteins. Second, granular aggregates of AgHalo displayed a less polar environment than aggregates formed by folded globular protein represented by Htt-polyQ. Third, our studies reveal that granular protein aggregates formed in response to different types of stressors exhibit significant polarity differences. These results show that the solvatochromic fluorophores solely responsive to polarity represent a new class of indicators that can be widely used for detecting protein aggregation in live cells, thus paving the way for elucidating cellular mechanisms of protein aggregation as well as therapeutic approaches to managing intracellular aggregates.

Dataset Information

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

Publications

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

Similar Datasets

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