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

• Published in: Organic & biomolecular chemistry 2013-08, Vol.11 (29), p.4764-4777
• Main Authors: Alvim, Haline G O, Fagg, Emma L, de Oliveira, Aline L, de Oliveira, Heibbe C B, Freitas, Sonia M, Xavier, Mary-Ann E, Soares, Thereza A, Gomes, Alexandre F, Gozzo, Fabio C, Silva, Wender A, Neto, Brenno A D
• Format: Article
• Language: English
• Subjects: Animals; Cattle; Chalcone - chemical synthesis; Chalcone - chemistry; Crystallography, X-Ray; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Models, Molecular; Molecular Structure; Photochemical Processes; Quantum Theory; Serum Albumin, Bovine - chemistry
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c3ob27331h

In the present manuscript, a novel fluorescent chalcone derivative is synthesized and its photophysical properties are fully characterized. The designed fluorophore is applied as a probe to study protein-dye interactions with bovine serum albumin. Circular dichroism gave interesting results on the thermodynamics of the interaction. NMR spectroscopy, especially relaxation measurements, revealed the atoms in the chalcone derivative that interacts with the protein upon binding. Molecular docking calculations indicate that the most favourable binding sites are near the two tryptophan residues. Furthermore, ab initio and DFT calculations offer insights into the reactivity and physicochemical properties of this novel fluorophore.