Evaluation of Antifungal Activity and Potential Application as Fluorescent Probes of Indolenine and Benzo[e]Indole-Based Squarylium Dyes

The antifungal performance and the possible use as fluorescent probes of a series of squarylium dyes derived from indolenine and benzo[e]indole previously synthesized was evaluated. Some photophysical properties were performed in ethanol and phosphate buffer, and the type of aggregates form in phosphate buffer was analyzed. Using the 1,3-diphenylisobenzofuran assay, a qualitative assessment of the capacity of dyes to produce singlet oxygen after irradiation was performed. Regarding the antifungal activity, this was studied through a broth microdilution assay using Saccharomyces cerevisiae PYCC 4072 as a biological model. The effect of irradiation of the dyes, with an appropriate light emitting diode system, on the antifungal activity was also evaluated, and it was verified that some of the dyes improve their activity after irradiation. Using fluorescence microscopy techniques, the colocalization of dyes in S. cerevisae cells was investigated and it was possible to verify that some of the squarylium dyes with a barbituric moiety in the four-membered central ring stained and accumulated preferentially in the mitochondrial web and perinuclear membrane of the cells. The possible use as a fluorescent probe for the detection of HSA was also evaluated for one of the dyes of the series, demonstrating a linear variation in the fluorescence intensity accompanied by the increase in the protein concentration.

Automated summary

The antifungal performance and fluorescent probe potential of a series of squarylium dyes derived from indolenine and benzo[e]indole were evaluated. Photophysical properties and aggregate formation in phosphate buffer were studied. Singlet oxygen production was assessed using the 1,3-diphenylisobenzofuran assay. Antifungal activity was tested using Saccharomyces cerevisiae PYCC 4072, and some of the dyes showed improved activity after irradiation. Colocalization in yeast cells and the potential as a fluorescent probe for HSA detection were investigated.