title: Rigid multivalent scaffolds based on adamantane.
abstract: We present two new synthetic strategies to rigid multivalent scaffolds of the general structure 1 based on adamantane. Both routes start from arylated adamantane derivatives and give the target compounds 12 and 18 in 5 and 7 steps, respectively. These scaffolds have been designed for the assembly of multivalent binders for cell surface epitopes. The adamantane nucleus exposes three carboxylic acid groups in a well-defined tripodal geometry for conjugation of targeting ligands. In addition, an amino group at the fourth bridgehead position provides a flexible linker for attachment of effector molecules such as contrast agents, radiotracers, or cytotoxins without interfering with the cell binding process.
authors.affiliation: Division of Hematology/Oncology, Department of Medicine, Beth Israel Deaconess Medical Center, SL-B05, 330 Brookline Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Khaled
authors.initials: K
authors.lastname: Nasr
authors.forename: Nadine
authors.initials: N
authors.lastname: Pannier
authors.forename: John V
authors.initials: JV
authors.lastname: Frangioni
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Maison
mesh_terms: D000218:Adamantane / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure
chemical_list: D008024:Ligands; D000218:Adamantane