Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules.
The selective recognition of substrates or cofactors is a key feature of biological processes. It involves coordination bonds, hydrogen bonding, charge/charge and charge/dipole interactions. In this Perspective, we describe how the calix[6]arene core can be functionalized and shaped to act as a biomimetic molecular receptor. The strategy relies on the selective introduction of three amino arms on alternate phenolic positions. Upon metal ion binding or self-assembly via multiple ion-pairing and H-bonding, these amino arms are projected towards each other, thus closing the calixarene small rim. The resulting cone-shaped receptors act as molecular funnels displaying high affinities for a variety of neutral guests. Their hosting properties can be finely tuned by changing the small or the large rim or by allosteric effects. Induced-fit processes are also often observed as the cavity can expand for large guests or shrink for small ones. Hence, the different families of calix[6]arene-based receptors presented here highlight the importance of having a flexible and polarized hydrophobic structure to accommodate the guest.
Coquière
David
D
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université Paris Descartes (Paris 5), 45 rue des Saints-Pères, 75006 Paris, France.
Le Gac
Stéphane
S
Darbost
Ulrich
U
Sénèque
Olivier
O
Jabin
Ivan
I
Reinaud
Olivia
O
D032701:Biomimetics; D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D004798:Enzymes / Q000737:chemistry / Q000378:metabolism; D008670:Metals / Q000737:chemistry / Q000378:metabolism; D009942:Organometallic Compounds / Q000737:chemistry / Q000378:metabolism; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
D004798:Enzymes; D008670:Metals; D009942:Organometallic Compounds; D010636:Phenols; C476540:calix(6)arene; D047250:Calixarenes