title: Cyclic DGR-peptidomimetic containing a bicyclic reverse turn inducer as a selective alpha(v)beta (5) integrin ligand.
abstract: 3-Aza-6,8-dioxabicyclo[3.2.1]octane-based amino acids as reverse turn inducers have been introduced into cyclic peptidomimetics containing the RGD or DGR retro-sequence, in order to achieve a stereochemical scanning of the binding capability of the resulting molecules towards alpha(v)beta(3) and alpha(v)beta(5) integrins, resulting in retro-inverso DGR peptides as micromolar ligands. A comparative analysis between the conformational preferences of 4 and of its isomer 3, having the opposite RGD sequence, was reported with respect to the binding activity, giving insight into the factors affecting the preferential binding of 4 to the alpha(v)beta(5) integrin.
authors.affiliation: Dipartimento di Chimica Organica Ugo Schiff, Polo Scientifico di Sesto Fiorentino, Università degli Studi di Firenze, Sesto Fiorentino, Florence, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Trabocchi
authors.forename: G
authors.initials: G
authors.lastname: Menchi
authors.forename: E
authors.initials: E
authors.lastname: Danieli
authors.forename: D
authors.initials: D
authors.lastname: Potenza
authors.forename: N
authors.initials: N
authors.lastname: Cini
authors.forename: A
authors.initials: A
authors.lastname: Bottoncetti
authors.forename: S
authors.initials: S
authors.lastname: Raspanti
authors.forename: A
authors.initials: A
authors.lastname: Pupi
authors.forename: Antonio
authors.initials: A
authors.lastname: Guarna
mesh_terms: D005260:Female; D006801:Humans; D007700:Kinetics; D008024:Ligands; D010456:Peptides, Cyclic / Q000819:agonists / Q000138:chemical synthesis / Q000737:chemistry*; D010920:Placenta / Q000737:chemistry / Q000378:metabolism; D011247:Pregnancy; D011485:Protein Binding; D019030:Receptors, Vitronectin / Q000737:chemistry* / Q000378:metabolism
chemical_list: D008024:Ligands; D010456:Peptides, Cyclic; D019030:Receptors, Vitronectin; C507169:cyclic arginine-glycine-aspartic acid peptide; C064660:integrin alphaVbeta5