Probing deep into the interaction of a fluorescent chalcone derivative and bovine serum albumin (BSA): an experimental and computational study

Haline G. O. Alvim, Emma L. Fagg, Aline L. de Oliveira, Heibbe C. B. de Oliveira, Sonia M. Freitas, Mary-Ann E. Xavier, Thereza A. Soares, Alexandre F. Gomes, Fabio C. Gozzo, Wender A. Silva, Brenno A. D. Neto
2013 Organic and biomolecular chemistry  
Materials and methods Chemicals and solvents were purchased from commercial sources and used without further purification. Synthesis of fluorescent chalcone 3 Chalcone derivative 3 was obtained from a classic aldol condensation (Claisen-Schmidt condensation) of aromatic aldehydes and aromatic ketones in excellent yield (90%) after purification. Ketone 1 (1 mmol) was added to a solution of NaOH (10% w/v or KOH) and ethanol (3 mL). The mixture was stirred for 20 min under ice bath cooling. After,
more » ... aldehyde 2 (1 mmol) was added and the resulting mixture was stirred for additional 12 hours at room temperature. The reaction mixture was acidified with HCl 10%. The precipitate was collected, washed with cold water, dried and purified by column chromatography (20% ethyl acetate/hexane). All NMR measurements were carried out on a Bruker Avance III spectrometer (11.75 T) operating at 500 MHz for 1 H and on a Varian Mercury Plus spectrometer (7.05 T) operating at 300 MHz for 1 H and at 75.46 MHz for 13 C.
doi:10.1039/c3ob27331h pmid:23680860 fatcat:hs6fjn4izbecrpvd4ot6cxrjfa