Cyclic phosphate-linked oligosaccharides (CyPLOS): Novel carbohydrate-based syntheticion transporters

Pure and Applied Chemistry

Volumn 84, Issue 1, 2012, Pages 87-96

  Montesarchio, Daniela ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Amphiphilic oligosaccharides; Glycomimetics; Ion transporters; Macrocycles; Phosphate bonds; Phosphate linked macrocycles; Self assembly; Synthetic ionophores

Indexed keywords

CARBOHYDRATES; DIMERS; ELECTROSPINNING; ETHERS; GLYCOLS; ION EXCHANGE; IONS; LIPID BILAYERS; MAGNETIC MOMENTS; OLIGOSACCHARIDES; PHOSPHOLIPIDS;

AMPHIPHILICS; CONFORMATIONAL PROPERTIES; CYCLIC DIMERS; FINE TUNING; FUNCTIONAL LEVELS; FUNCTIONALIZATIONS; FUNCTIONALIZED; GLYCOMIMETICS; ION CHANNEL; ION TRANSPORTERS; MACROCYCLES; MECHANISM OF ACTION; NATURALLY OCCURRING; PHOSPHODIESTERS; PHOSPHOLIPID BILAYER; PHOSPHOLIPID MEMBRANE; POLYETHER CHAINS; SPIN LABEL; SYNTHETIC IONOPHORES; SYNTHETIC MOLECULES; TETRAETHYLENE GLYCOLS;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

EID: 84930483572     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-11-09-19     Document Type: Article

References (27)

1. S. Matile, A. Vargas Jentzsch, J. Montenegro, A. Fin. Chem. Soc. Rev. 40, 2453 (2011)
2. N. Sakai, J. Mareda, S. Matile. Mol. BioSyst. 3, 658 (2007);
3. L. Adam, L. Sisson, M. Raza Shah, S. Bhosale, S. Matile. Chem. Soc. Rev. 35, 1269 (2006).
4. J. T. Davis, O. Okunola, R. Quesada. Chem. Soc. Rev. 39, 3843 (2010)
5. F. Sansone, L. Baldini, A. Casnati, R. Ungaro. New J. Chem. 34, 2715 (2010)
6. G. W. Gokel, I. A. Carasel. Chem. Soc. Rev. 36, 378 (2007).
7. I. Tabushi, Y. Kuroda, K. Yokota. Tetrahedron Lett. 23, 4601 (1982).
8. N. Madhavan, E. C. Robert, M. S. Gin. Angew. Chem., Int. Ed. 44, 7584 (2005).
9. F. Sallas, R. Darcy. Journal Eur. J. Org. Chem. 6, 957 (2008).
10. G. Gattuso, S. A. Nepogodiev, J. F. Stoddart. Chem. Rev. 98, 1919 (1998).
11. L. Fan, O. Hindsgaul. Org. Lett. 4, 4503 (2002).
12. B. Hoffmann, B. Bernet, A. Vasella. Helv. Chim. Acta 85, 265 (2002).
13. E. Locardi, M. Stockle, S. Gruner, H. Kessler. J. Am. Chem. Soc. 123, 8189 (2001)
14. M. Ménand, J.-C. Blais, L. Hamon, J.-M. Valéry, J. Xie. J. Org. Chem. 70, 4423 (2005).
15. M. Ménand, J.-C. Blais, J.-M. Valéry, J. Xie. J. Org. Chem. 71, 3295 (2006).
16. K. Bodine, D. Y. Gin, M. S. Gin. Org. Lett. 7, 4479 (2005).
17. D. Rodríguez-Lucena, J. M. Benito, E. Álvarez, C. Jaime, J. Perez-Miron, C. Ortiz Mellet, J. M. García Fernández. J. Org. Chem. 73, 2967 (2008).
18. G. Di Fabio, A. Randazzo, J. D'Onofrio, L. De Napoli, D. Montesarchio. J. Org. Chem. 71, 3395 (2006).
19. C. Coppola, J. D'Onofrio, G. Di Fabio, L. De Napoli, D. Montesarchio. Eur. J. Org. Chem. 23, 3849 (2007).
20. C. Coppola, V. Saggiomo, G. Di Fabio, L. De Napoli, D. Montesarchio. J. Org. Chem. 72, 9679 (2007).
21. G. Mangiapia, C. Coppola, G. Vitiello, G. D'Errico, L. De Napoli, A. Radulescu, D. Montesarchio, L. Paduano. J. Colloid Interface Sci. 354, 718 (2011).
22. S. Licen, C. Coppola, J. D'Onofrio, D. Montesarchio, P. Tecilla. Org. Biomol. Chem. 7, 1060 (2009).
23. For the HPTS assay, liposomes (100 nm diameter) incorporating the fluorescent dye are prepared in a 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) buffer (pH 7.0) containing NaCl (or MCl and NaX in the experiments for cation and anion selectivity, respectively; 100 mM) and, once the ionophore is added, the external pH is suddenly brought to 7.6 by addition of NaOH (or MOH in experiments for cation selectivity) and the fluorescence emission of the dye recorded. In brief, the increase in fluorescence may be directly correlated with an increase in H+ efflux and/or OH- influx through the liposomes in response to the pH gradient, mediated by the ionophore under investigation. For more details, see also refs. [17,19] in this list, and V. Gorteau, G. Bollot, J. Mareda, S. Matile. Org. Biomol. Chem. 5, 3000 (2007).
24. C. Coppola, A. Paciello, G. Mangiapia, S. Licen, M. Boccalon, L. De Napoli, L. Paduano, P. Tecilla, D. Montesarchio. Chem.-Eur. J. 16, 13757 (2010).
25. A. R. Katritzky, D. C. Fara, H. Yang, K. Tamm, T. Tamm, M. Karelson. Chem. Rev. 104, 175 (2004).
26. C. Coppola, L. Simeone, L. De Napoli, D. Montesarchio. Eur. J. Org. Chem. 6, 1155 (2011).
27. G. Vitiello, E. Busi, C. Coppola, D. Montesarchio, R. Basosi, L. Paduano, G. D'Errico. Manuscript in preparation.