Recognition in water of bioactive substrates by a sulphonato p-tert-butylcalix[5]arene

REFERENCES

• (a) Gringrich, J.A.; Caron, M.G. Annu. Rev. Neurosci. 1993, 16, 299–321; (b) Jackson, D.M.; Westlind-Danielsson, A. Pharmacol. Ther. 1994, 64, 291–370; (c) Lefkowitz, R.J. Angew. Chem. Int. Ed. 2013, 52, 6367–6378; (d) Kobilka, B. Angew. Chem. Int. Ed. 2013, 52, 6380–6388.
   Google Scholar
• (a) Ni, X.-L.; Rahman, S.; Wang, S.; Jin, C.-C.; Zeng, X.; Hughes, D.L.; Redshaw, C.; Yamato, T. Org. Biomol. Chem. 2012, 10, 4618–4626; (b) Perraud, O.; Lefevre, S.; Robert, V.; Martinez, A.; Dutasta, J.-P. Org. Biomol. Chem. 2012, 10, 1056–1059; (c) Le Gac, S.; Picron, J.-F.; Reinaud, O.; Jabin, I. Org. Biomol. Chem. 2011, 9, 2387–2396; (d) Givelet, C.; Bibal, B. Org. Biomol. Chem. 2011, 9, 7457–7460; (e) Späth, A.; König, B. Beilstein J. Org. Chem. 2010, 6, No. 32; (f) Chui, J.K.W.; Fyles, T.M. Supramol. Chem. 2008, 20, 397–405; (g) Saijo, R.; Tsunekawa, S.; Murakami, H.; Shirai, N.; Ikeda, S.-I.; Odashima, K. Biorg. Med. Chem. Lett. 2007, 17, 767–771; (h) Kim, J.; Raman, B.; Ahn, K.H. J. Org. Chem. 2006, 71, 38–45; (i) Secor, K.E.; Glass, T.E. Org. Lett. 2004, 6, 3727–3730; (j) Molt, O.; Rübeling, D.; Schäfer, G.; Schrader, T. Chem. Eur. J. 2004, 10, 4225–4232; (k) Katsu, T.; Ido, K.; Tsubaki, K.; Fuji, K. Electroanalysis 2003, 15, 287–293; (l) Paugam, M.-F.; Bien, J.T.; Smith, B.D.; Chrisstoffels, L.A.J.; de Jong, F.; Reinhoudt, D.N. J. Am. Chem. Soc. 1996, 118, 9820–9825.
   Google Scholar
• (a) Sotnikova, T.D.; Caron, M.G.; Gainetdinov, R.R. Mol. Pharmacol. 2009, 76, 229–235; (b) Hyland, K. Clin. Chem. 2008, 54, 633–641; (c) Davidson, D.F. Ann. Clin. Biochem. 2005, 42, 200–207.
   Google Scholar
• (a) Gargiulli, C.; Gattuso, G.; Notti, A.; Pappalardo, S., Parisi, M.F.; Puntoriero, F. Tetrahedron 2012, 53, 616–619; (b) Gattuso, G.; Liantonio, R.; Meyer, F.; Metrangolo, P.; Pappalardo, A.; Parisi, M.F.; Pilati, T.; Pisagatti, I.; Resnati, G. Supramol. Chem. 2006, 18, 235–243; (c) Ferguson, G.; Gallagher, J.F.; Lough, A.J.; Notti, A.; Pappalardo, S.; Parisi, M.F. J. Org. Chem. 1999, 64, 5876–5885.
   Google Scholar
• (a) Lupo, F.; Capici, C.; Gattuso, G.; Notti, A.; Parisi, M.F.; Pappalardo, A.; Pappalardo, S.; Gulino, A. Chem. Mater. 2010, 22, 2829–2834; (b) Gargiulli, C.; Gattuso, G.; Liotta, C.; Notti, A.; Parisi, M.F.; Pisagatti, I.; Pappalardo, S. J. Org. Chem. 2009, 74, 4350–4353; (c) Ballisteri, F.P.; Notti, A.; Pappalardo, S.; Parisi, M.F.; Pisagatti, I. Org. Lett. 2003, 5, 1071–1074; (d) Arnaud-Neu, F.; Fuangswasdi, S.; Notti, A.; Pappalardo, S.; Parisi, M.F. Angew. Chem. Int. Ed. 1998, 37, 112–114.
   Google Scholar
• Gattuso, G. ; Notti, A. ; Pappalardo, A. ; Pappalardo, S. ; Parisi, M.F. ; Puntoriero, F. Tetrahedron Lett. 2013, 54, 188–191.
   Web of Science ®Google Scholar
• Wang, C. ; Wang, Z. ; Zhang, X. Acc. Chem. Res. 2012, 45, 608–618.
   PubMed Web of Science ®Google Scholar
• For a recent example of a calix[6]arene-based receptor, capable of forming ternary complexes in water with primary amines and other biologically relevant amines in the presence of zinc(II), see: (a) Bistri, O.; Colasson, B.; Reinaud, O. Chem. Sci. 2012, 3, 811–818. For pertinent reviews on the properties of p-sufonatocalix[n]arenes, see: (b) Perret, F.; Lazar, A.N., Coleman, A.W. Chem. Commun. 2011, 47, 7303–7319; (c) Guo, D.-S.; Wang, K.; Liu, Y. J. Inclusion Phenom. Macrocyclic Chem. 2008, 62, 1–21.
   Google Scholar
• Henderson, T.J. Anal. Chem. 2002, 74, 191–198.
   PubMed Web of Science ®Google Scholar
• (a) Capici, C.; Gattuso, G.; Notti, A.; Parisi, M.F.; Pappalardo, S.; Brancatelli G.; Geremia, S. J. Org. Chem. 2012, 77, 9668–9675; (b) Gattuso, G.; Notti, A.; Pappalardo S.; Parisi, M.F.; Pilati T.; Terraneo, G. CrystEngComm 2012, 14, 2621–2625; (c) Gattuso, G.; Notti, A.; Pappalardo S.; Parisi, M.F.; Pilati T.; Resnati, G.; Terraneo, G. CrystEngComm 2009, 11, 1204–1206.
   Google Scholar
• Brancatelli, G. ; Capici, C. ; Gattuso, G. ; Geremia, S. ; Notti, A. ; Parisi, M.F. ; Pappalardo, S. ; Parisi, M.F. ; Sortino, S. ; Vittorino, E. Chem. Asian J. 2012, 7, 50–54.
   PubMed Web of Science ®Google Scholar
• The self-assembly of an anionic surfactant, promoted by a hydrotropic salt (benzylammonium chloride), has recently been described. See: Lin, Y.; Qiao, Y.; Cheng, X.; Yan, Y.; Li, Z.; Huang, J. J. Coll. Interface Sci. 2012, 369, 238–244.
   Google Scholar
• In organic solvents, p-tert-butylcalix[5]arenes are known to selectively bind inside the π-rich cavity only unbranched primary alkylammonium ions. See: Giannetto, M.; Mori, G.; Notti, A.; Pappalardo, S.; Parisi, M.F. Anal. Chem. 1998, 70, 4631–4635; as well as Ref. (5d).
   Google Scholar