title: Human serum albumin as vehicle for the solubilization of perylene diimides in aqueous solutions.
abstract: The chemical, physical and photophysical properties of perylene diimides have attracted substantial attention for the potential applications in diverse fields ranging from advanced materials to biomedical applications. Some applications require the diimides to be in aqueous environment where they tend to dissolve poorly. We investigated the use of human serum albumin as a vehicle to increase the aqueous exposure of monomeric perylene diimides. Since studies on the interactions of these compounds with protein is scarce we characterized the binding and the possible effects on the protein. In order to increase the affinity of the dyes to the protein we have used perylene diimides with substituents that replicate the side chains of natural amino acids. The results show that only the dyes containing the side chain of leucine and phenylalanine yield measurable binding. Only the phenylalanine analogue promotes energy transfer with the lone tryptophan residue of albumin indicating different binding modalities for the dyes. In addition, this analogue is the only one which shows photochemical activity that prompts its release from the protein upon laser irradiation.
authors.affiliation: Department of Physics and Astronomy, University of Texas at San Antonio, San Antonio, TX, USA.
authors.forename: Mohammed J
authors.initials: MJ
authors.lastname: Farooqi
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, TX, USA.
authors.forename: Mark A
authors.initials: MA
authors.lastname: Penick
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, TX, USA.
authors.forename: George R
authors.initials: GR
authors.lastname: Negrete
authors.affiliation: Department of Physics and Astronomy, University of Texas at San Antonio, San Antonio, TX, USA. Electronic address: lorenzo.brancaleon@utsa.edu.
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Brancaleon
mesh_terms: D006801:Humans; D007094:Imides / Q000737:chemistry*; D062105:Molecular Docking Simulation; D010569:Perylene / Q000737:chemistry*; D011485:Protein Binding; D012709:Serum Albumin / Q000737:chemistry*; D012995:Solubility; D012996:Solutions
chemical_list: D007094:Imides; D012709:Serum Albumin; D012996:Solutions; D010569:Perylene
keywords: Perylene diimides; Protein binding; Resonance energy transfer