LeHavreV1, Istex, Corpus, bibRecord, 000A05

Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

Identifieur interne : 000A05 ( Istex/Corpus ); précédent : 000A04; suivant : 000A06

Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

Auteurs : David Coquire ; Stphane Le Gac ; Ulrich Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr-Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France. ; Olivier Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs-Cea-Ujf Rue Des Martyrs Grenoble Cedex France. ; Ivan Jabin ; Olivia Reinaud

Source :

Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2009.

RBID : ISTEX:EABA382D532EB5EA33CD5C32B05A43E14B9ABC94

Abstract

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.

Url:

https://api.istex.fr/document/EABA382D532EB5EA33CD5C32B05A43E14B9ABC94/fulltext/pdf

DOI: 10.1039/b902456e

Links to Exploration step

ISTEX:EABA382D532EB5EA33CD5C32B05A43E14B9ABC94

Le document en format XML

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<front><div type="abstract">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.</div>
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<json:item><name>Olivier SnquePresent address: Laboratoire de Chimie et Biologie des Mtaux, UMR 5249 CNRS-CEA-UJF, 17 rue des Martyrs, 38054 Grenoble Cedex 9, France.</name>
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<abstract>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.</abstract>
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<notesStmt><note>Calix[6]arenes shaped into conic funnels through biomimetic coordination chemistry or self-assembling display remarkable hosting properties for a wide variety of neutral guest molecules. The versatility of the system allows tuning and switching behaviours.</note>
<note>Chem. Rev., 1997, 97, 12321734</note>
<note>Chem. Rev., 1998, 98, 17412076</note>
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<email>Olivia.reinaud@parisdescartes.fr</email>
<note type="biography">David Coquire obtained his PhD in 2006 under the supervision of Prof. O. Reinaud, at Paris Descartes University. Then, he moved to Groningen, The Netherlands, to join Prof. Feringa's group as a post-doctoral fellow for two years and worked on asymmetric catalysis based on biopolymer (DNA, protein) under the supervision of Dr Roelfes. He is now working in a biotech company at Lyon, France.</note>
<affiliation>David Coquire obtained his PhD in 2006 under the supervision of Prof. O. Reinaud, at Paris Descartes University. Then, he moved to Groningen, The Netherlands, to join Prof. Feringa's group as a post-doctoral fellow for two years and worked on asymmetric catalysis based on biopolymer (DNA, protein) under the supervision of Dr Roelfes. He is now working in a biotech company at Lyon, France.</affiliation>
<affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris, France</affiliation>
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<author xml:id="author-2"><persName><forename type="first">Stphane</forename>
<surname>Le Gac</surname>
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<note type="biography">Stphane Le Gac completed his PhD in organic chemistry in 2006 under the supervision of Prof. I. Jabin, at Le Havre University. After a first postdoctoral period at the Free University of Brussels, Belgium, he joined the group of Prof. R. Nolte in Nijmegen, The Netherlands, where he is currently working as a postdoctoral fellow on the selective functionalization of chromophoric nanowires.</note>
<affiliation>Stphane Le Gac completed his PhD in organic chemistry in 2006 under the supervision of Prof. I. Jabin, at Le Havre University. After a first postdoctoral period at the Free University of Brussels, Belgium, he joined the group of Prof. R. Nolte in Nijmegen, The Netherlands, where he is currently working as a postdoctoral fellow on the selective functionalization of chromophoric nanowires.</affiliation>
<affiliation>Unit de Recherche en Chimie Organique et Macromolculaire (URCOM), Universit du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France</affiliation>
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<author xml:id="author-3"><persName><forename type="first">Ulrich</forename>
<surname>DarbostPresent address: ICBMS, Institut de Chimie et Biochimie Molculaire et Supramolculaire, UMR-CNRS 5246, Universit de Lyon, Universit Claude Bernard Lyon 1, CPE Lyon, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France.</surname>
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<note type="biography">Ulrich Darbost obtained his PhD in 2004 under the supervision of Prof. I. Jabin, at Le Havre University. Then he moved to Montreal, Canada, to join Prof. J. D. Wuest's group as a post-doctoral fellow to work on molecular tectonics. He went back to France in 2006 and he is currently assistant professor at the University of Lyon, where he is carrying out research on calixarenes.</note>
<affiliation>Ulrich Darbost obtained his PhD in 2004 under the supervision of Prof. I. Jabin, at Le Havre University. Then he moved to Montreal, Canada, to join Prof. J. D. Wuest's group as a post-doctoral fellow to work on molecular tectonics. He went back to France in 2006 and he is currently assistant professor at the University of Lyon, where he is carrying out research on calixarenes.</affiliation>
<affiliation>Unit de Recherche en Chimie Organique et Macromolculaire (URCOM), Universit du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France</affiliation>
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<author xml:id="author-4"><persName><forename type="first">Olivier</forename>
<surname>SnquePresent address: Laboratoire de Chimie et Biologie des Mtaux, UMR 5249 CNRS-CEA-UJF, 17 rue des Martyrs, 38054 Grenoble Cedex 9, France.</surname>
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<email>Olivia.reinaud@parisdescartes.fr</email>
<note type="biography">Olivier Snque obtained a PhD from the University of Paris XI under the supervision of Prof. Olivia Reinaud in 2002. Then he spent two postdoctoral years in the group of Pascale Delangle at the CEA-Greanoble before being appointed as a CNRS researcher in 2004. His current interest is focused on metallopeptides.</note>
<affiliation>Olivier Snque obtained a PhD from the University of Paris XI under the supervision of Prof. Olivia Reinaud in 2002. Then he spent two postdoctoral years in the group of Pascale Delangle at the CEA-Greanoble before being appointed as a CNRS researcher in 2004. His current interest is focused on metallopeptides.</affiliation>
<affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris, France</affiliation>
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<author xml:id="author-5"><persName><forename type="first">Ivan</forename>
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</persName>
<email>ijabin@ulb.ac.be</email>
<note type="biography">Ivan Jabin was born in 1968 in France. He obtained his PhD in Organic Chemistry from the Pierre et Marie Curie University (ESPCI-UPMC) in 1996 and then spent two years as a post-doctoral fellow, first at Lehigh University (USA) and then at the Conservatoire National de Paris des Arts et Mtiers (Paris, France). In 1998, he was named an assistant Professor of Chemistry at the University of Le Havre (France). After eight years, he joined the Free University of Brussels (Belgium) as a full Professor. His current research interests include the synthesis and study of new classes of molecular receptors. Ivan Jabin and Olivia Reinaud have been collaborating since 2000.</note>
<affiliation>Ivan Jabin was born in 1968 in France. He obtained his PhD in Organic Chemistry from the Pierre et Marie Curie University (ESPCI-UPMC) in 1996 and then spent two years as a post-doctoral fellow, first at Lehigh University (USA) and then at the Conservatoire National de Paris des Arts et Mtiers (Paris, France). In 1998, he was named an assistant Professor of Chemistry at the University of Le Havre (France). After eight years, he joined the Free University of Brussels (Belgium) as a full Professor. His current research interests include the synthesis and study of new classes of molecular receptors. Ivan Jabin and Olivia Reinaud have been collaborating since 2000.</affiliation>
<affiliation>Unit de Recherche en Chimie Organique et Macromolculaire (URCOM), Universit du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France</affiliation>
<affiliation>Laboratoire de Chimie Organique, Universit Libre de Bruxelles (U.L.B.), Avenue F. D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium</affiliation>
</author>
<author xml:id="author-6"><persName><forename type="first">Olivia</forename>
<surname>Reinaud</surname>
</persName>
<email>Olivia.reinaud@parisdescartes.fr</email>
<note type="biography">Olivia Reinaud completed a PhD in organic chemistry (1987, Dr M. Maumy, ESPCI-UPMC) and after a one-year postdoc in biochemistry (Dr D. Mansuy, Paris Descartes University), she was appointed CNRS researcher and developed novel biomimetic copper catalyzed processes (ESPCI). She took a two year sabbatical in inorganic chemistry (Delaware University, USA, Prof. K. Theopold). Upon return to France, she started a new project associating organic, inorganic and supramolecular chemistry with some bio-inspiration. Since 2001, she has had a full Professorship at Paris Descartes. Her current research interest lies in Supramolecular Bio-Inorganic Chemistry, dealing with biomimetic metal complexes based on calix[6]arene derivatives.</note>
<affiliation>Olivia Reinaud completed a PhD in organic chemistry (1987, Dr M. Maumy, ESPCI-UPMC) and after a one-year postdoc in biochemistry (Dr D. Mansuy, Paris Descartes University), she was appointed CNRS researcher and developed novel biomimetic copper catalyzed processes (ESPCI). She took a two year sabbatical in inorganic chemistry (Delaware University, USA, Prof. K. Theopold). Upon return to France, she started a new project associating organic, inorganic and supramolecular chemistry with some bio-inspiration. Since 2001, she has had a full Professorship at Paris Descartes. Her current research interest lies in Supramolecular Bio-Inorganic Chemistry, dealing with biomimetic metal complexes based on calix[6]arene derivatives.</affiliation>
<affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris, France</affiliation>
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 </published>
 <art-front>
 <titlegrp>
 <title>Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules</title>
 </titlegrp>
 <authgrp>
 <author aff="affa">
 <person>
 <persname>
 <fname>David</fname>
 <surname>Coquière</surname>
 </persname>
 <biography>
 <section>
 <plate id="plt1" src="plt1">
 </plate>
 <p>David Coquière obtained his PhD in 2006 under the supervision of Prof. O. Reinaud, at Paris Descartes University. Then, he moved to Groningen, The Netherlands, to join Prof. Feringa's group as a post-doctoral fellow for two years and worked on asymmetric catalysis based on biopolymer (DNA, protein) under the supervision of Dr Roelfes. He is now working in a biotech company at Lyon, France.</p>
 </section>
 </biography>
 </person>
 </author>
 <author aff="affb">
 <person>
 <persname>
 <fname>Stéphane</fname>
 <surname>Le Gac</surname>
 </persname>
 <biography>
 <section>
 <plate id="plt2" src="plt2">
 </plate>
 <p>Stéphane Le Gac completed his PhD in organic chemistry in 2006 under the supervision of Prof. I. Jabin, at Le Havre University. After a first postdoctoral period at the Free University of Brussels, Belgium, he joined the group of Prof. R. Nolte in Nijmegen, The Netherlands, where he is currently working as a postdoctoral fellow on the selective functionalization of chromophoric nanowires.</p>
 </section>
 </biography>
 </person>
 </author>
 <author aff="affb">
 <person>
 <persname>
 <fname>Ulrich</fname>
 <surname>Darbost<fnoteref></fnoteref>
<footnote id="fn1"><p>Present address: ICBMS, Institut de Chimie et Biochimie Moléculaire et Supramoléculaire, UMR-CNRS 5246, Université de Lyon, Université Claude Bernard Lyon 1, CPE Lyon, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France.</p>
</footnote>
</surname>
 </persname>
 <biography>
 <section>
 <plate id="plt3" src="plt3">
 </plate>
 <p>Ulrich Darbost obtained his PhD in 2004 under the supervision of Prof. I. Jabin, at Le Havre University. Then he moved to Montreal, Canada, to join Prof. J. D. Wuest's group as a post-doctoral fellow to work on molecular tectonics. He went back to France in 2006 and he is currently assistant professor at the University of Lyon, where he is carrying out research on calixarenes.</p>
 </section>
 </biography>
 </person>
 </author>
 <author aff="affa">
 <person>
 <persname>
 <fname>Olivier</fname>
 <surname>Sénèque<fnoteref></fnoteref>
<footnote id="fn2"><p>Present address: Laboratoire de Chimie et Biologie des Métaux, UMR 5249 CNRS-CEA-UJF, 17 rue des Martyrs, 38054 Grenoble Cedex 9, France.</p>
</footnote>
</surname>
 </persname>
 <biography>
 <section>
 <plate id="plt4" src="plt4">
 </plate>
 <p>Olivier Sénèque obtained a PhD from the University of Paris XI under the supervision of Prof. Olivia Reinaud in 2002. Then he spent two postdoctoral years in the group of Pascale Delangle at the CEA-Greanoble before being appointed as a CNRS researcher in 2004. His current interest is focused on metallopeptides.</p>
 </section>
 </biography>
 </person>
 </author>
 <author aff="affb affc" role="corres">
 <person>
 <persname>
 <fname>Ivan</fname>
 <surname>Jabin</surname>
 </persname>
 <biography>
 <section>
 <plate id="plt5" src="plt5">
 </plate>
 <p>Ivan Jabin was born in 1968 in France. He obtained his PhD in Organic Chemistry from the Pierre et Marie Curie University (ESPCI-UPMC) in 1996 and then spent two years as a post-doctoral fellow, first at Lehigh University (USA) and then at the Conservatoire National de Paris des Arts et Métiers (Paris, France). In 1998, he was named an assistant Professor of Chemistry at the University of Le Havre (France). After eight years, he joined the Free University of Brussels (Belgium) as a full Professor. His current research interests include the synthesis and study of new classes of molecular receptors. Ivan Jabin and Olivia Reinaud have been collaborating since 2000.</p>
 </section>
 </biography>
 </person>
 </author>
 <author aff="affa" role="corres">
 <person>
 <persname>
 <fname>Olivia</fname>
 <surname>Reinaud</surname>
 </persname>
 <biography>
 <section>
 <plate id="plt6" src="plt6">
 </plate>
 <p>Olivia Reinaud completed a PhD in organic chemistry (1987, Dr M. Maumy, ESPCI-UPMC) and after a one-year postdoc in biochemistry (Dr D. Mansuy, Paris Descartes University), she was appointed CNRS researcher and developed novel biomimetic copper catalyzed processes (ESPCI). She took a two year sabbatical in inorganic chemistry (Delaware University, USA, Prof. K. Theopold). Upon return to France, she started a new project associating organic, inorganic and supramolecular chemistry with some “bio-inspiration”. Since 2001, she has had a full Professorship at Paris Descartes. Her current research interest lies in “Supramolecular Bio-Inorganic Chemistry”, dealing with biomimetic metal complexes based on calix[6]arene derivatives.</p>
 </section>
 </biography>
 </person>
 </author>
 <aff id="affa">
 <org>
 <orgname>
 <nameelt>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques</nameelt>
 <nameelt>UMR CNRS 8601</nameelt>
 <nameelt>Université Paris Descartes (Paris 5)</nameelt>
 </orgname>
 </org>
 <address>
 <addrelt>45 rue des Saints-Pères</addrelt>
 <city>75006 Paris</city>
 <country>France</country>
 </address>
 <email>Olivia.reinaud@parisdescartes.fr</email>
 <fax>+33-1-42-86-21-83</fax>
 </aff>
 <aff id="affb">
 <org>
 <orgname>
 <nameelt>Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM)</nameelt>
 <nameelt>Université du Havre</nameelt>
 </orgname>
 </org>
 <address>
 <addrelt>25 rue Philippe Lebon</addrelt>
 <addrelt>BP 540</addrelt>
 <city>76058 Le Havre cedex</city>
 <country>France</country>
 </address>
 </aff>
 <aff id="affc">
 <org>
 <orgname>
 <nameelt>Laboratoire de Chimie Organique</nameelt>
 <nameelt>Université Libre de Bruxelles (U.L.B.)</nameelt>
 </orgname>
 </org>
 <address>
 <addrelt>Avenue F. D. Roosevelt 50</addrelt>
 <addrelt>CP160/06</addrelt>
 <city>B-1050 Brussels</city>
 <country>Belgium</country>
 </address>
 <email>ijabin@ulb.ac.be</email>
 <fax>+32-2-650-27-98</fax>
 </aff>
 </authgrp>
 <art-toc-entry>
 <ictext>Calix[6]arenes shaped into conic <it>funnels</it>
 through biomimetic coordination chemistry or self-assembling display remarkable hosting properties for a wide variety of neutral guest molecules. The versatility of the system allows tuning and switching behaviours.</ictext>
 <icgraphic id="ga" src="ga" pos="fixed"></icgraphic>
 </art-toc-entry>
 <abstract>
 <p>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 <it>via</it>
 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.</p>
 </abstract>
 </art-front>
 <art-back>
 <ack>
 <p>We acknowledge support from the CNRS, Ministère de la Recherche (O.S., D.C. and S.L.G.), Région Haute-Normandie (Doctoral f. for U. D.), and l′Agence Nationale pour la Recherche (Calixzyme project: ANR-05-BLAN-0003) for funding. We also acknowledge fruitful collaborations with Marie-Noëlle Rager, Michel Luhmer, Michel Giorgi, Jérôme Marrot and Thierry Prangé for NMR and XRD analyses.</p>
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<mods version="3.6"><titleInfo><title>Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules</title>
</titleInfo>
<titleInfo type="alternative" contentType="CDATA"><title>Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules</title>
</titleInfo>
<name type="personal"><namePart type="given">David</namePart>
<namePart type="family">Coquire</namePart>
<affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris, France</affiliation>
<affiliation>E-mail: Olivia.reinaud@parisdescartes.fr</affiliation>
<description>David Coquire obtained his PhD in 2006 under the supervision of Prof. O. Reinaud, at Paris Descartes University. Then, he moved to Groningen, The Netherlands, to join Prof. Feringa's group as a post-doctoral fellow for two years and worked on asymmetric catalysis based on biopolymer (DNA, protein) under the supervision of Dr Roelfes. He is now working in a biotech company at Lyon, France.</description>
</name>
<name type="personal"><namePart type="given">Stphane</namePart>
<namePart type="family">Le Gac</namePart>
<affiliation>Unit de Recherche en Chimie Organique et Macromolculaire (URCOM), Universit du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France</affiliation>
<description>Stphane Le Gac completed his PhD in organic chemistry in 2006 under the supervision of Prof. I. Jabin, at Le Havre University. After a first postdoctoral period at the Free University of Brussels, Belgium, he joined the group of Prof. R. Nolte in Nijmegen, The Netherlands, where he is currently working as a postdoctoral fellow on the selective functionalization of chromophoric nanowires.</description>
</name>
<name type="personal"><namePart type="given">Ulrich</namePart>
<namePart type="family">DarbostPresent address: ICBMS, Institut de Chimie et Biochimie Molculaire et Supramolculaire, UMR-CNRS 5246, Universit de Lyon, Universit Claude Bernard Lyon 1, CPE Lyon, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France.</namePart>
<affiliation>Unit de Recherche en Chimie Organique et Macromolculaire (URCOM), Universit du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France</affiliation>
<description>Ulrich Darbost obtained his PhD in 2004 under the supervision of Prof. I. Jabin, at Le Havre University. Then he moved to Montreal, Canada, to join Prof. J. D. Wuest's group as a post-doctoral fellow to work on molecular tectonics. He went back to France in 2006 and he is currently assistant professor at the University of Lyon, where he is carrying out research on calixarenes.</description>
</name>
<name type="personal"><namePart type="given">Olivier</namePart>
<namePart type="family">SnquePresent address: Laboratoire de Chimie et Biologie des Mtaux, UMR 5249 CNRS-CEA-UJF, 17 rue des Martyrs, 38054 Grenoble Cedex 9, France.</namePart>
<affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris, France</affiliation>
<affiliation>E-mail: Olivia.reinaud@parisdescartes.fr</affiliation>
<description>Olivier Snque obtained a PhD from the University of Paris XI under the supervision of Prof. Olivia Reinaud in 2002. Then he spent two postdoctoral years in the group of Pascale Delangle at the CEA-Greanoble before being appointed as a CNRS researcher in 2004. His current interest is focused on metallopeptides.</description>
</name>
<name type="personal"><namePart type="given">Ivan</namePart>
<namePart type="family">Jabin</namePart>
<affiliation>Unit de Recherche en Chimie Organique et Macromolculaire (URCOM), Universit du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France</affiliation>
<affiliation>Laboratoire de Chimie Organique, Universit Libre de Bruxelles (U.L.B.), Avenue F. D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium</affiliation>
<affiliation>E-mail: ijabin@ulb.ac.be</affiliation>
<description>Ivan Jabin was born in 1968 in France. He obtained his PhD in Organic Chemistry from the Pierre et Marie Curie University (ESPCI-UPMC) in 1996 and then spent two years as a post-doctoral fellow, first at Lehigh University (USA) and then at the Conservatoire National de Paris des Arts et Mtiers (Paris, France). In 1998, he was named an assistant Professor of Chemistry at the University of Le Havre (France). After eight years, he joined the Free University of Brussels (Belgium) as a full Professor. His current research interests include the synthesis and study of new classes of molecular receptors. Ivan Jabin and Olivia Reinaud have been collaborating since 2000.</description>
</name>
<name type="personal"><namePart type="given">Olivia</namePart>
<namePart type="family">Reinaud</namePart>
<affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris, France</affiliation>
<affiliation>E-mail: Olivia.reinaud@parisdescartes.fr</affiliation>
<description>Olivia Reinaud completed a PhD in organic chemistry (1987, Dr M. Maumy, ESPCI-UPMC) and after a one-year postdoc in biochemistry (Dr D. Mansuy, Paris Descartes University), she was appointed CNRS researcher and developed novel biomimetic copper catalyzed processes (ESPCI). She took a two year sabbatical in inorganic chemistry (Delaware University, USA, Prof. K. Theopold). Upon return to France, she started a new project associating organic, inorganic and supramolecular chemistry with some bio-inspiration. Since 2001, she has had a full Professorship at Paris Descartes. Her current research interest lies in Supramolecular Bio-Inorganic Chemistry, dealing with biomimetic metal complexes based on calix[6]arene derivatives.</description>
</name>
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<originInfo><publisher>The Royal Society of Chemistry.</publisher>
<dateIssued encoding="w3cdtf">2009</dateIssued>
<copyrightDate encoding="w3cdtf">2009</copyrightDate>
</originInfo>
<language><languageTerm type="code" authority="iso639-2b">eng</languageTerm>
<languageTerm type="code" authority="rfc3066">en</languageTerm>
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<abstract>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.</abstract>
<note>Calix[6]arenes shaped into conic funnels through biomimetic coordination chemistry or self-assembling display remarkable hosting properties for a wide variety of neutral guest molecules. The versatility of the system allows tuning and switching behaviours.</note>
<note displayLabel="cit6">Chem. Rev., 1997, 97, 12321734</note>
<note displayLabel="cit12">Chem. Rev., 1998, 98, 17412076</note>
<relatedItem type="host"><titleInfo><title>Organic & Biomolecular Chemistry</title>
</titleInfo>
<titleInfo type="abbreviated"><title>Org. Biomol. Chem.</title>
</titleInfo>
<genre type="journal">journal</genre>
<originInfo><publisher>The Royal Society of Chemistry.</publisher>
</originInfo>
<identifier type="ISSN">1477-0520</identifier>
<identifier type="eISSN">1477-0539</identifier>
<identifier type="coden">OBCRAK</identifier>
<identifier type="RSC sercode">OB</identifier>
<part><date>2009</date>
<detail type="volume"><caption>vol.</caption>
<number></number>
</detail>
<detail type="issue"><caption>no.</caption>
<number>12</number>
</detail>
<extent unit="pages"><start>2485</start>
<end>2500</end>
<total>16</total>
</extent>
</part>
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<identifier type="DOI">10.1039/b902456e</identifier>
<identifier type="ms-id">b902456e</identifier>
<accessCondition type="use and reproduction" contentType="copyright">This journal is © The Royal Society of Chemistry</accessCondition>
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<recordOrigin>The Royal Society of Chemistry</recordOrigin>
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Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

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