Click synthesis of triazole-linked calix[4]arene ionophores. Potentiometric and ESI-MS screening of ion-selectivity

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 78, Issue 1-4, 2014, Pages 207-215

  Czirok, János B ^a   Jágerszki, Gyula ^a   Tóth, Klára ^a   Révész, Ágnes ^b   Drahos, László ^b   Bitter, István ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

1,2,3 Triazole; Calix 4 arene ionophore; Click chemistry; ESI MS; Ion selectivity; PVC membrane electrode

Indexed keywords

EID: 84893781848     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-013-0289-y     Document Type: Article

References (33)

1. Kolb, H.C.; Finn, M.G.; Sharpless, K.B.: Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021 (2001)
2. Bock, V.D.; Hiemstra, H.; van Maarseveen, J.H.: Cu(I)-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 1, 51-68 (2006)
3. Finn, M.G.; Fokin, V. (eds.): Applications of click chemistry themed issue. Chem. Soc. Rev. 39, 1231-1405 (2010)
4. Moses, J.E.; Moorhouse, A.D.: The growing application of click chemistry. Chem. Soc. Rev. 36, 1249-1262 (2007)
5. Morales-Sanfrutos, J.; Ortega-Muñoz, M.; Lopez-Jaramillo, J.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F.: Synthesis of calixarene-based cavitands and nanotubes by click chemistry. J. Org. Chem. 73, 7768-7771 (2008)
6. 2+ ions. Tetrahedron Lett. 48, 7274-7278 (2007)
7. 2+ based on triazole coupled ortho- methoxyphenylazocalix[4]arene. Tetrahedron 67, 8131-8139 (2011)
8. - switched INHIBIT logic gate with a YES logic function. Eur. J. Org. Chem. 24, 4700-4704 (2010)
9. 2+ in blood serum milieu. Chem. Commun. 46, 4345-4347 (2010)
10. 2+ and as biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein. J. Org. Chem. 76, 10039-10049 (2011)
11. 2+. J. Org. Chem. 73, 8212-8218 (2008)
12. Li, H.; Zhan, J.; Chen, M.; Tian, D.; Zou, Z.: Metal ions recognition by 1,2,3-triazolium calix[4]arene esters synthesized via click chemistry. J. Incl. Phenom. Macrocycl. Chem. 66, 43-47 (2010)
13. Kim, J.S.; Park, S.Y.; Kim, S.H.; Thuery, P.; Souane, R.; Matthews, S.E.; Vicens, J.: A pyrenyl-appended triazole-based calix[4]arene as a fluorescent sensor for iodine ion. Bull. Korean Chem. Soc. 31, 624-629 (2010)
14. Di Marco, V.B.; Bombi, G.G.: Electrospray mass spectrometry (ESI-MS) in the study of metal-ligand solution equilibria. Mass Spectrom. Rev. 25, 347 (2006)
15. Daniel, J.M.; Friess, S.D.; Rajagopalan, S.; Wendt, S.; Zenobi, R.: Quantitative determination of noncovalent binding interactions using soft ionization mass spectrometry. Int. J. Mass Spectrom. 216, 1-27 (2002)
16. Veenstra, T.D.: Electrospray ionization mass spectrometry in the study of biomolecular non-covalent interactions. Biophys. Chem. 79, 63-79 (1999)
17. Brodbelt, J.S.: Probing molecular recognition by mass spectrometry. Int. J. Mass Spectrom. 200, 57-69 (2000)
18. Loo, J.A.: Studying noncovalent protein complexes by electrospray ionization mass spectrometry. Mass Spectrom. Rev. 16, 1-23 (1997)
19. Wang, K.; Gokel, G.W.: The use of mass spectrometry to assess complexation phenomena in receptor compounds. Pure Appl. Chem. 68, 1267-1272 (1996)
20. Leize, E.; Jaffrezic, A.; Van Dorsselaer, A.: Correlation between solvation energies and electrospray mass spectrometric response factors. Study by electrospray mass spectrometry of supramolecular complexes in thermodynamic equilibrium in solution. J. Mass Spectrom. 31, 537-544 (1996)
21. Blair, S.M.; Kempen, E.C.; Brodbelt, J.S.: Determination of binding selectivities in host-guest complexation by electrospray/quadrupole ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 9, 1049 (1998)
22. Rosu, F.; De Pauw, E.; Gabelica, V.: Electrospray mass spectrometry to study drug-nucleic acids interactions. Biochimie 90, 1074 (2008)
23. Rosu, F.; Gabelica, V.; Claude, H.; De Pauw, E.: Determination of affinity, stoichiometry and sequence selectivity of minor groove binder complexes with double-stranded oligodeoxynucleotides by electrospray ionization mass spectrometry. Nucleic Acids Res. 30, e82 (2002)
24. Wang, W.; Kitova, E.N.; Klassen, J.S.: Influence of solution and gas phase processes on protein-carbohydrate binding affinities determined by nanoelectrospray Fourier transform ion cyclotron resonance mass spectrometry. Anal. Chem. 75, 4945-4955 (2003)
25. Révész, Á.; Schröder, D.; Svec, J.; Wimmerova, M.; Sindelar, V.: Anion binding by bambus[6]uril probed in the gas phase and in solution. J. Phys. Chem. A 115, 11378-11386 (2011)
26. Umezawa, Y.; Bühlmann, P.; Umezawa, K.; Tohda, K.; Amemiya, S.: Potentiometric selectivity coefficients of ion-selective electrodes part I. Inorganic cations (Technical Report). Pure Appl. Chem. 72, 1851-2082 (2000)
27. Girard, C.; Önen, E.; Aufort, M.; Beauvière, S.; Samson, E.; Herscovici, J.: Reusable polymer-supported catalyst for the [3 + 2] Huisgen cycloaddition in automation protocols. Org. Lett. 8, 1689-1692 (2006)
28. Asfari, Z.; Bilyk, A.; Bond, C.; Harrowfield, J.M.; Koutsantonis, G.A.; Lengkeek, N.; Mocerino, M.; Skelton, B.W.; Sobolev, A.N.; Strano, S.; Vicens, J.; White, A.H.: Factors influencing solvent adduct formation by calixarenes in the solid state. Org. Biomol. Chem. 2, 387-396 (2004)
29. Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C.J.; Russell, T.P.; Wu, P.; Fokin, V.V.: Structurally diverse dendritic libraries: a highly efficient functionalization approach using click chemistry. Macromolecules 38, 3663-3678 (2005)
30. Sa, M.M.; Ramos, M.D.; Fernandes, L.: Fast and efficient preparation of Baylis-Hillman-derived (E)-allylic azides and related compounds in aqueous medium. Tetrahedron 62, 11652-11656 (2006)
31. +-selective sensors with nanomolar detection limit. Chem. Commun. 46, 607-609 (2010)
32. Jágerszki, G.; Takács, Á.; Bitter, I.; Gyurcsányi, E.R.: Solid-state ion channels for potentiometric sensing. Angew. Chem. Int. Ed. 50, 1-5 (2011)
33. + complexes generated by electrospray ionization. Int. J. Mass Spectrom. 219, 729-738 (2002)