Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biolog
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ORIGINAL PAPER
Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities Przemysław Krawczyk 1 Received: 30 June 2020 / Accepted: 13 September 2020 / Published online: 19 September 2020 # The Author(s) 2020
Abstract The study presents the influence of structure modulation by introducing selected donor and acceptor substituents on optical properties of benzofuran used in biological imaging. As the starting form, 2-(5-formylbenzofuran-2-yl)acetamide described experimentally was used. This molecule contains an aldehyde group as reactive site, through which conjugation with protein occurs. Structure modulation was carried out by attaching additional electron-donating and electron-withdrawing substituents to the amino group, namely -NH2, -NHCH3, -NO2, -OH, and -OCH3. Studies have shown that the -NH2, -NHCH3, -OH, and -OCH3 substituents do not induce a significant change in the position of maximum absorption and fluorescence relative to each other. They also do not change the parameters describing the nonlinear response. Only the presence of the -NO2 substituent results in significant solvatochromic shifts. Changing substituents also does not significantly affect the LD50 value, and all tested fluorescent probes should not be considered toxic to humans. Modulation of the benzofuran derivative structure also does not change the active center in which the biocomplex with the protein is formed. In each case, the conjugation takes place via LYS114. In addition, the study was prompted to analyze the linear and nonlinear optical properties of conjugates formed after the reaction with Concanavalin A.
Keywords Linear and nonlinear optical properties . Bioimaging . Conjugation with proteins . Biological activities . Toxicology . Solvatochromism . Benzofuran Abbreviations XCon Marker determination after conjugation ConA Concanavalin A THF Tetrahydrofuran MeAc Acetone MeCN Acetonitrile DMF n,n-Dimethylformamide DMSO Dimethylsulfoxide
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00894-020-04539-6) contains supplementary material, which is available to authorized users. * Przemysław Krawczyk [email protected] 1
Collegium Medicum, Faculty of Pharmacy, Department of Physical Chemistry, Nicolaus Copernicus University, Kurpińskiego 5, 85-950 Bydgoszcz, Poland
Introduction Benzofuran, because of its structure made of fused benzene and furan rings, can be classified as a heterocyclic organic compound. It is mainly utilized in the production of coumarone resins and it occurs naturally in the form of a colorless, oily liquid. Light oils obtained during coal tar distillation are the main source of this compound. There are several fields of application of benzofuran including organic synthesis, where it is used as a constituent for more complex systems, as well as material science. It is also widely found in many molecules that are biologically significant. Several different biological activities can be attribu
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