Host-guest chemistry of aromatic-amide-linked bis- and tris-calix[4] pyrroles with bis-carboxylates and citrate anion

Grazia Cafeo, Giuseppe Gattuso, Franz H. Kohnke, Georgia Papanikolaou, Aldo Profumo, Camillo Rosano

Research output: Contribution to journalArticlepeer-review

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 1H NMR complexation studies. Calixpyrrole receptors: Compounds 1 a and 1 b with p- or m-phthaloyl or trimesic chloride have been used to prepare bis-and tris-calixpyrrole receptors (see figure). The polytopic receptors were tested as ligands of various bis-carboxylates and citrate (see structure on the right). The binding modes in the complexes were explored and depend on the stereochemical match between the host and guest.

Original languageEnglish
Pages (from-to)1658-1668
Number of pages11
JournalChemistry - A European Journal
Volume20
Issue number6
DOIs
Publication statusPublished - Feb 3 2014

Keywords

  • calixarenes
  • carboxylate ligands
  • hydrogen bonds
  • molecular modeling
  • molecular recognition

ASJC Scopus subject areas

  • Chemistry(all)

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