Experimental and computational studies of protolytic and tautomeric equilibria of Erythrosin B and Eosin Y in water/DMSO

Vanzin, Douglas; Freitas, Camila Fabiano de; Pellosi, Diogo Silva; Batistela, Vagner Roberto; Machado, Antônio Eduardo da Hora; Pontes, Rodrigo M.; Caetano, Wilker; Hioka, Noboru

doi:10.1039/c6ra12198e

Cited by 33 publications

(42 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The p K a value for the anionic dye of the stronger acid, i.e., erythrosin B, eosin Y, and fluorescein, is lower, indicating that the dye possesses a more negative charge. 12−15 The p K a values for the proton dissociation between the anion and dianion for erythrosin B, eosin Y, and fluorescein are 3.79, 3.80, and 6.43, respectively. 13,14 The adsorption or deposition of the neutral or cationic dye (rhodamine B) and cationic dye (rhodamine 6G) did not significantly increase.…”

Section: Resultsmentioning

confidence: 99%

“…11 There are several xanthene dyes possessing different charge or p K a values, which are available to probe the titania surface. 12−15 In this study, titania films were prepared by a simple sol–gel method to observe changes in the titania surface charge during UV irradiation. The dye molecules were “adsorbed” and “deposited” on the titania films from their aqueous solutions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

In Situ Probing of Photoinduced Hydrophilicity on Titania Surface Using Dye Molecules

et al. 2019

View full text Add to dashboard Cite

The titania film surface exhibits superhydrophilicity after UV irradiation due to its photocatalytic function. This is caused by a change in the density of the surface hydroxyl groups, which affects the surface charge density. Titania films were prepared to observe the change in the surface charge during UV irradiation. The amounts of some xanthene dyes adsorbed and deposited on the titania films after UV irradiation were evaluated as a function of the irradiation time. The increase in the adsorption and deposition amounts of the more negative dye versus the UV irradiation time was greater. These results indicated that the titania surface charge became more positive by the UV irradiation. It was reported that basic hydroxyl groups formed on the titania particle surface during the UV irradiation. The surface dissociates hydroxyl ions into the water phase and has a positive charge, which was supported by the present study.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In Situ Probing of Photoinduced Hydrophilicity on Titania Surface Using Dye Molecules

et al. 2019

View full text Add to dashboard Cite

show abstract

“…S20c). A lower LUMO energy means the compound could also be more easily reduced to the radical anion, which is known to occur with xanthene dyes 29,30 This may explain why rose bengal, which has the most electropositive charge density, is able to bind in a very positive protein pocket -if in fact it must first be reduced to the radical anion. Indeed, xanthenes like eosin Y and rose bengal have been reported to act as strong electron acceptors when they are in a photoexcited state, oxidizing thiols to thiyl radicals 27 , and oxidizing lysine and arginine residues 28 .…”

Section: Discussionmentioning

confidence: 99%

Discovery and characterization of halogenated xanthene inhibitors of DUSP5 as potential photodynamic therapeutics

Bongard

Lepley

Gastonguay³

et al. 2019

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

to protein characterization and interpretation of results; Aided in manuscript preparation. Rachel A. Jones Lipinsky: Conducted chemical synthesis and characterization. Noah R. Leigh: Contributed to the automation aspect of the screen, and helped facilitate the screen. Raman G. Kutty: Contributed to the development and optimization of the pNPP assay; intellectual contribution to project design and interpretation of results. Daniel S. Sem: Key role in guiding group members in the characterization of DUSP5 enzyme kinetics and activity; aided in all aspects of project direction, compiled, prepared and edited the manuscript. Rajendra Rathore: Key role in guiding group members in the characterization of DUSP5/ERK interactions via molecular dynamic simulations. Ramani Ramchandran: Key role in guiding group members in the characterization of DUSP5 activity and purification; aided in all aspects of project direction, compiled, prepared and edited the manuscript.

show abstract

“…In solution, eosin Y can exist in three different forms as neutral (H2R), monoanionic (HR -) and di anionic (R 2-) forms, where R denotes the anionic part of the eosin Y as explained in fig. 3 [3][4]. The ionization constants (pKa1 and pKa2) of eosin Y were reported as 2.9 and 4.5 [5].…”

Section: Fig 1: Structure Of Eosinsmentioning

confidence: 99%

Utilization of Eosin Dye as an Ion Pairing Agent for Determination of Pharmaceuticals: A Brief Review

Rahman

2017

Int J Pharm Pharm Sci

View full text Add to dashboard Cite

Globally, dyes are widely used in the pharmaceutical, food, textile, cosmetics, plastics, leather, paint, ink and paper industries. Eosin is an acidic orange-pink dye and has very strong staining properties. Haematoxylin and eosin Y (H and E) combination is the most common staining and primary diagnostic technique in histo-pathological laboratories. This review mainly discussed the utility of eosin dye in quality control laboratories as an ion pairing agent for drug analysis. Eosin Y is one the most common ion pairing agent and its mono and di anionic forms are capable of interacting with many drug molecules to form colored/fluorescent binary or ternary complexes that can be analyzed with or without extraction by spectrofluorimetry and/or spectrophotometry. Quenching fluorescence and advantages of spectrofluorimetry over spectrophotometry were also discussed. Fluorescence detection greatly enhances the sensitivity and providing a sensitive and relatively inexpensive instrumental method of analysis using eosin Y for various important drugs in pure, commercial dosage forms and biological fluids.

show abstract

Experimental and computational studies of protolytic and tautomeric equilibria of Erythrosin B and Eosin Y in water/DMSO

Abstract: The pKa of Eosin Y and Erythrosin B were experimentally and computationally studied in water/DMSO mixtures using UV-Vis spectra, orbital and electrostatic properties to understand the tautomers contribution in the protolithic equilibria.

Cited by 33 publications

References 59 publications

In Situ Probing of Photoinduced Hydrophilicity on Titania Surface Using Dye Molecules

In Situ Probing of Photoinduced Hydrophilicity on Titania Surface Using Dye Molecules

Discovery and characterization of halogenated xanthene inhibitors of DUSP5 as potential photodynamic therapeutics

Utilization of Eosin Dye as an Ion Pairing Agent for Determination of Pharmaceuticals: A Brief Review

Contact Info

Product

Resources

About