Reverse solvatochromism in a family of probes having 2,6–di–tert–butylphenolate as electron–donor and 4–nitrophenyl as electron–acceptor groups

Melo, Carlos E. A. de; Nicoleti, Celso R.; Ferreira, Misael; Santos, Miriã C. dos; Kreuz, Adrian; Schneider, Felipe S. S.; Oliboni, Robson S.; Caramori, Giovanni F.; Machado, Vanderlei G.

doi:10.1016/j.dyepig.2022.110376

Cited by 7 publications

(1 citation statement)

References 83 publications

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“…In lower polarity solvents, positive solvatochromism occurs as the solvents become more polar (moving from right to left in Figure 3 a). At some medium polarity points, a reversal is seen and a negative solvatochromism trend follows as the solvents become more polar (again moving from right to left in Figure 3 a) [ 40 ]. The trends seen for Cy5.5-mannotetraose in dilutions of DMSO are similar to that of increasing concentrations of PEG-ConA.…”

Section: Resultsmentioning

confidence: 99%

A Polarity-Sensitive Far-Red Fluorescent Probe for Glucose Sensing through Skin

Colvin

Dunlap

et al. 2023

Biosensors

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The field of glucose biosensors for diabetes management has been of great interest over the past 60 years. Continuous glucose monitoring (CGM) is important to continuously track the glucose level to provide better management of the disease. Concanavalin A (ConA) can reversibly bind to glucose and mannose molecules and form a glucose biosensor via competitive binding. Here, we developed a glucose biosensor using ConA and a fluorescent probe, which generated a fluorescent intensity change based on solvatochromism, the reversible change in the emission spectrum dependent on the polarity of the solvent. The direction in which the wavelength shifts as the solvent polarity increases can be defined as positive (red-shift), negative (blue-shift), or a combination of the two, referred to as reverse. To translate this biosensor to a subcutaneously implanted format, Cyanine 5.5 (Cy5.5)-labeled small mannose molecules were used, which allows for the far-red excitation wavelength range to increase the skin penetration depth of the light source and returned emission. Three Cy5.5-labeled small mannose molecules were synthesized and compared when used as the competing ligand in the competitive binding biosensor. We explored the polarity-sensitive nature of the competing ligands and examined the biosensor’s glucose response. Cy5.5-mannotetraose performed best as a biosensor, allowing for the detection of glucose from 25 to 400 mg/dL. Thus, this assay is responsive to glucose within the physiologic range when its concentration is increased to levels needed for an implantable design. The biosensor response is not statistically different when placed under different skin pigmentations when comparing the percent increase in fluorescence intensity. This shows the ability of the biosensor to produce a repeatable signal across the physiologic range for subcutaneous glucose monitoring under various skin tones.

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Section: Resultsmentioning

confidence: 99%

A Polarity-Sensitive Far-Red Fluorescent Probe for Glucose Sensing through Skin

Colvin

Dunlap

et al. 2023

Biosensors

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Empirical Hydrogen Bonding Donor (HBD) Parameters of Organic Solvents Using Solvatochromic Probes – A Critical Evaluation

Spange

Weiß

2023

ChemPhysChem

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The solvatochromicity of established solvatochromic UV/Vis probes, which appear to be sensitive to the so-called hydrogen bond donor (HBD) property of the solvent, is analysed using the hydroxyl group density of alcoholic solvents D HBD as a physical parameter in comparison to the pKa, the chemical benchmark for acidity. Reichardt's dye B30, Kosowers Z-indicator 1-ethyl-4-(methoxycarbonyl) pyridinium iodide (K), Kamlet-Tafts α, Dragos S parameter, Catalans SA scale, the cis-dicyano-bis (1,10phenanthroline) iron II complex (Schilt's Ferrocyphen dye, Fe) and Gutmann's acceptor number (AN) have been investigated. The observed dependencies of the empirical polarity parameters as a function of D HBD for several alcoholic solvent families requires a ompletely new physicochemical understanding of these established HBD parameters. Only the AN scale (or Fe) is able to bridge the gap between global polarity and acidity, provided the values are interpreted correctly and applied accordingly.

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Exploring solvatochromism: A comprehensive analysis of research data

Homocianu

2024

Microchemical Journal

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Reverse solvatochromism in a family of probes having 2,6–di–tert–butylphenolate as electron–donor and 4–nitrophenyl as electron–acceptor groups

Cited by 7 publications

References 83 publications

A Polarity-Sensitive Far-Red Fluorescent Probe for Glucose Sensing through Skin

A Polarity-Sensitive Far-Red Fluorescent Probe for Glucose Sensing through Skin

Empirical Hydrogen Bonding Donor (HBD) Parameters of Organic Solvents Using Solvatochromic Probes – A Critical Evaluation

Exploring solvatochromism: A comprehensive analysis of research data

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