Spectroscopic behavior of bufotenine and bufotenine N-oxide: Solvent and pH effects and interaction with biomembrane models

• Published in: Biochimica et biophysica acta. Biomembranes 2024-04, Vol.1866 (4), p.184304, Article 184304
• Main Authors: Almeida e Silva, Gustavo, Galvão Wakui, Vinícius, Kato, Lucília, Marquezin, Cássia A.
• Format: Article
• Language: English
• Subjects: Bufotenine; Fluorescence; Liposome; Micelle; UV/visible spectroscopy
• ISSN: 0005-2736; 1879-2642; 1879-2642
• DOI: 10.1016/j.bbamem.2024.184304

Bufotenine is a fluorescent analog of Dimethyltryptamine (DMT) that has been widely studied due to its psychedelic properties and biological activity. However, little is known about its spectroscopic properties in different media. Thus, we present in this work, for the first time, the spectroscopic behavior of bufotenine and bufotenine N-oxide by means of their fluorescence properties. Both molecules exhibit changes in optical absorption and emission spectra with variations in pH of the medium and in different solvents. Assays in the presence of biomembranes models, like micelles and liposomes, were also performed. In surfactants titration experiments, the spectral shift observed in fluorescence shows the interaction of both molecules with pre-micellar structures and with micelles. Steady state anisotropy measurements show that both bufotenine and bufotenine N-oxide, in the studied concentration range, interact with liposomes without causing changes in the fluidity of the lipid bilayer. These results can be useful in studies that aim at searching for new compounds, inspired by bufotenine and bufotenine N-oxide, with relevant pharmacological activities and also in studies that use these molecules as markers of psychiatric disorders. [Display omitted] •For the first time: fluorescence properties of bufotenine and bufotenine N-oxide.•Bufotenine and its oxide interact with SDS and CTAB micelles and DMPC liposomes.•Deprotonation of the hydroxyl group of bufotenine was observed by fluorescence.