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image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Spectrochimica Acta ...arrow_drop_down
image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao
Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy
Article . 2017 . Peer-reviewed
License: Elsevier TDM
Data sources: Crossref
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Solvatochromism and linear solvation energy relationship of the kinase inhibitor SKF86002

Authors: Muhammad Khattab; Madeline Van Dongen; Feng Wang; Andrew H.A. Clayton;

Solvatochromism and linear solvation energy relationship of the kinase inhibitor SKF86002

Abstract

We studied the spectroscopic characteristics of SKF86002, an anti-inflammatory and tyrosine kinase inhibitor drug candidate. Two conformers SKF86002A and SKF86002B are separated by energy barriers of 19.68kJ·mol(-1) and 6.65kJ·mol(-1) due to H-bonds, and produce the three major UV-Vis absorption bands at 325nm, 260nm and 210nm in cyclohexane solutions. This environment-sensitive fluorophore exhibited emission in the 400-500nm range with a marked response to changes in environment polarity. By using twenty-two solvents for the solvatochromism study, it was noticed that solvent polarity, represented by dielectric constant, was well correlated with the emission wavelength maxima of SKF86002. Thus, the SKF86002 fluorescence peak red shifted in aprotic solvents from 397.5nm in cyclohexane to 436nm in DMSO. While the emission maximum in hydrogen donating solvents ranged from 420nm in t-butanol to 446nm in N-methylformamide. Employing Lippert-Mataga, Bakhshiev and Kawski models, we found that one linear correlation provided a satisfactory description of polarity effect of 18 solvents on the spectral changes of SKF86002 with R(2) values 0.78, 0.80 and 0.80, respectively. Additionally, the multicomponent linear regression analysis of Kamlet-Taft (R(2)=0.94) revealed that solvent acidity, basicity and polarity accounted for 31%, 24% and 45% of solvent effects on SKF86002 emission, respectively. While Catalán correlation (R(2)=0.92) revealed that solvatochromic change of SKF86002 emission was attributed to changes in solvent dipolarity (71%), solvent polarity (12%), solvent acidity (11%) and solvent basicity (6%). Plot of Reichardt transition energies and emission energies of SKF86002 in 18 solvents showed also a linear correlation with R(2)=0.90. The dipole moment difference between excited and ground state was calculated to be 3.4-3.5debye.

Country
Australia
Related Organizations
Keywords

Imidazoles, Molecular Conformation, Hydrogen Bonding, 541, Solutions, Thiazoles, Spectrometry, Fluorescence, Cyclohexanes, Linear Models, Solvents, Thermodynamics, Spectrophotometry, Ultraviolet, Protein Kinase Inhibitors

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
4
Average
Average
Average
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