title: Host-guest chemistry of aromatic-amide-linked bis- and tris-calix[4]pyrroles with bis-carboxylates and citrate anion.
abstract: A small library of polytopic receptors has been synthesized from meso-p- and meso-m-aminophenylcalix[4]pyrroles and p- or m-phthaloyl or trimesic chloride. Selected bis-carboxylates and the citrate anion, which either exhibit altered distribution profiles in cancerous tissues in comparison with healthy tissues or are metabolites of carcinogenic substances (for example, trans,trans-muconic acid from benzene exposure in humans) were tested as ligands. Varied affinities and binding modes were observed as a function of the number of calix[4]pyrroles and the topology of amide units present in each of the polytopic receptors. The structures of the 1:1 complexes derived by molecular modeling are in excellent agreement with the results of (1)H NMR complexation studies.
authors.affiliation: Dipartimento di Scienze Chiniche, Universitá di Messina viale F. Stagno D'Alcontres 31, 98166 Messina (Italy).
authors.forename: Grazia
authors.initials: G
authors.lastname: Cafeo
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Gattuso
authors.forename: Franz H
authors.initials: FH
authors.lastname: Kohnke
authors.forename: Georgia
authors.initials: G
authors.lastname: Papanikolaou
authors.forename: Aldo
authors.initials: A
authors.lastname: Profumo
authors.forename: Camillo
authors.initials: C
authors.lastname: Rosano
mesh_terms: D000577:Amides / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D019343:Citric Acid / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D011166:Porphyrins / Q000737:chemistry*
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D011166:Porphyrins; C469811:calix(4)pyrrole; D047250:Calixarenes; D019343:Citric Acid
keywords: calixarenes; carboxylate ligands; hydrogen bonds; molecular modeling; molecular recognition