title: Raman optical activity spectra and conformational elucidation of chiral drugs. The case of the antiangiogenic aeroplysinin-1.
abstract: We present the determination of the conformational properties of aeroplysinin-1 in aqueous solution by means of a combined experimental and theoretical Raman optical activity (ROA) and vibrational circular dichroism (VCD) study. Aeroplysinin-1 is an antiangiogenic drug extracted from the sponge Aplysina cavernicola which has been proved to be a valuable candidate for the treatment of cancer and other antiangiogenic diseases. Our study shows that this molecule possesses the 1S,6R absolute configuration in aqueous solution, where only two conformers are present to a significant level. We discuss in detail the relationships between the chiro-optical ROA and VCD features, and the structural properties of various energy accessible conformers are described. The present work is one of the first studies in which both ROA and VCD have been used as complementary tools for the determination of absolute configuration and dominant solution-state conformations of an unknown therapeutically significant molecule.
authors.affiliation: Departamento de Quimica Fisica, Universidad de Málaga, 29071 Málaga, Spain.
authors.forename: Belén
authors.initials: B
authors.lastname: Nieto-Ortega
authors.forename: Juan
authors.initials: J
authors.lastname: Casado
authors.forename: Ewan W
authors.initials: EW
authors.lastname: Blanch
authors.forename: Juan T
authors.initials: JT
authors.lastname: López Navarrete
authors.forename: Ana R
authors.initials: AR
authors.lastname: Quesada
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Ramírez
mesh_terms: D000097:Acetonitriles / Q000737:chemistry*; D020533:Angiogenesis Inhibitors / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013059:Spectrum Analysis, Raman; D013237:Stereoisomerism
chemical_list: D000097:Acetonitriles; D020533:Angiogenesis Inhibitors; D053138:Cyclohexenes; C042151:aeroplysinin I