Host–Guest Chemistry of Aromatic‐Amide‐Linked Bis‐ and Tris‐Calix[4]pyrroles with Bis‐Carboxylates and Citrate Anion |
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| Authors: | Dr Grazia Cafeo Dr Giuseppe Gattuso Prof Franz H Kohnke Dr Georgia Papanikolaou Dr Aldo Profumo Dr Camillo Rosano |
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| Affiliation: | 1. Dipartimento di Scienze Chiniche, Universitá di Messina viale F. Stagno D'Alcontres 31, 98166 Messina (Italy);2. IRCCS A.O.U. San Martino‐IST, Istituto Nazionale per la Ricerca sul Cancro, Largo R. Benzi 10, 16132 Genova (Italy) |
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| Abstract: | A small library of polytopic receptors has been synthesized from meso‐p‐ and meso‐m‐aminophenylcalix4]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 calix4]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. |
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| Keywords: | calixarenes carboxylate ligands hydrogen bonds molecular modeling molecular recognition |
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