Host–Guest Chemistry of Aromatic‐Amide‐Linked Bis‐ and Tris‐Calix[4]pyrroles with Bis‐Carboxylates and Citrate Anion. Issue 6 (8th January 2014)

• Record Type: Journal Article
• Authors: Cafeo, Grazia; Gattuso, Giuseppe; Kohnke, Franz H.; Papanikolaou, Georgia; Profumo, Aldo; Rosano, Camillo
• Is Part Of: Chemistry. Volume 20:Issue 6(2014)
• Page Start: 1658
• Page End: 1668
• Publication Date: 2014-01-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201303265
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A small library of polytopic receptors has been synthesized from <italic>meso</italic>‐<italic>p</italic>‐ and <italic>meso</italic>‐<italic>m</italic>‐aminophenylcalix[4]pyrroles and <italic>p</italic>‐ or <italic>m</italic>‐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, <italic>trans</italic>, <italic>trans</italic>‐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 ¹H NMR complexation studies.</p> </abstract>