Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

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 -NH(2), -NHCH(3), -NO(2), -OH, and -OCH(3). Studies have shown that the -NH(2), -NHCH(3), -OH, and -OCH(3) 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 -NO(2) substituent results in significant solvatochromic shifts. Changing substituents also does not significantly affect the LD(50) 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. Graphical abstract [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00894-020-04539-6) contains supplementary material, which is available to authorized users.