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Calixarenes in Molecular Recognition

Molecular Recognition

  1. Laura Baldini,
  2. Francesco Sansone,
  3. Alessandro Casnati,
  4. Rocco Ungaro

Published Online: 15 MAR 2012

DOI: 10.1002/9780470661345.smc052

Supramolecular Chemistry: From Molecules to Nanomaterials

Supramolecular Chemistry: From Molecules to Nanomaterials

How to Cite

Baldini, L., Sansone, F., Casnati, A. and Ungaro, R. 2012. Calixarenes in Molecular Recognition. Supramolecular Chemistry: From Molecules to Nanomaterials. .

Author Information

  1. Università di Parma, Parma, Italy

Publication History

  1. Published Online: 15 MAR 2012

Abstract

This chapter summarizes the most important aspects of the chemistry of calixarenes and their applications in supramolecular chemistry. The first section gives a short summary of the synthesis and conformational properties of calixarenes and of their functionalization at the phenolic OH groups (lower rim) and at the para-position of the aromatic nuclei (upper rim). The second section covers the properties of native and functionalized calixarenes (including chiral compounds) as receptors for the selective recognition of neutral molecules, cations, anions, and ion-pairs in the solid state, organic media, and water solution. In the third section, the calixarenes are viewed as scaffolds for the construction of multivalent ligands able to target biomacromolecules eliciting or inhibiting a biological process. Calixarene glycoclusters, operating as efficient and selective multivalent inhibitors of vegetal and mammalian lectins; peptidocalixarenes, capable of disrupting protein–protein interactions; and guanidino-calixarenes, able to target proteins or to condense DNA, acting, in this case, as efficient nonviral vectors for cell transfection, are discussed. When relevant, the use of calixarene receptors and multivalent ligands as active components of sensor devices for the detection of various analytes is also reported. Perspectives for future developments of calixarenes in supramolecular chemistry and bionanotechnology are indicated.

Keywords:

  • calixarenes;
  • carbohydrate recognition;
  • cavitands;
  • cell transfection;
  • glycocalixarenes;
  • ion recognition;
  • molecular inclusion;
  • multivalency;
  • peptidocalixarenes;
  • protein recognition