Complexing photolabile cholinergic ligands with synthetic and biological receptors: A dynamic survey

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 65, Issue 1, 2009, Pages 157-163

  Specht, A ^a   Loudwig, S ^b   Peng, L ^c   Goeldner, M ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b SOUTHWESTERN UNIVERSITY   (United States)

^c AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

Bioorganic chemistry; Calixarenes; Ligand receptor interactions; Photochemistry

Indexed keywords

EID: 76349086423     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9603-0     Document Type: Article

References (38)

1. Pillai, N. R.: Photoremovable protecting groups in organic synthesis. Synthesis. 1-26 (1980).
2. Bochet, C. G.: Photolabile protecting groups and linkers. J. Chem. Soc. Perkin Trans. 1(2), 125-142 (2002).
3. Pelliccioli, A. P., Wirz, J.: Photoremovable protecting groups: reaction mechanisms and applications. Photochem. Photobio. Sci. 1(7), 441-458 (2002).
4. Marriott, G. (ed.): Caged Compounds, Methods in Enzymol., vol. 291. Academic Press, New York (1998).
5. Goeldner, M., Givens, R. (eds.): Dynamic Studies in Biology. Wiley-VCH, weinheim (2005).
6. Ellis-Davies, G. C.: Caged compounds: photorelease technology for control of cellular chemistry and physiology. Nat. Methods. 4(8), 619-628 (2007).
7. Mayer, G., Heckel, A.: Biologically active molecules with a "light switch". Angew. Chem. Int. Ed. Engl. 45(30), 4900-4921 (2006).
8. Bourgeois, D., Weik, M.: New perspectives in kinetic protein crystallography using caged compounds. In: Goeldner, M., Givens, R. (eds.) Dynamic Studies in Biology, Phototriggers, Photoswitches and Caged Biomolecules, pp. 410-434. Wiley-VCH, Weinheim (2005).
9. Taylor, P., Radic, Z.: The cholinesterases: from genes to proteins. Annu. Rev. Pharmacol. Toxicol. 34, 281-320 (1994).
10. Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L., Silman, I.: Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein. Science 253, 872-879 (1991).
11. Harel, M., Schalk, I., Ehret-Sabatier, L., Bouet, F., Goeldner, M., Hirth, C., Axelsen, P. H., Silman, I., Sussman, J. L.: Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase. Proc. Natl. Acad. Sci. USA. 90, 9031-9035 (1993).
12. Nicolet, Y., Lockridge, O., Masson, P., Fontecilla-Camps, J.-C., Nachon, F.: Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J. Biol. Chem. 278, 41141-41147 (2003).
13. Peng, L., Goeldner, M.: Photoregulation of cholinesterase activities with caged cholinergic ligand. Methods Enzymol. 291, 265-278 (1998).
14. Gutsche, C. D.: Calixarene. Royal Society of Chemistry, Cambridge (1989).
15. Gutsche, C. D.: Calixarene Revisited. Royal Society of Chemistry, Cambridge (1998).
16. Vicens, J., Böhmer, V. (eds.): Calixarenes: A versatile class of macrocyclic compounds (Topics in inclusion science), vol. 3, Kluwer, Dordrecht (1991).
17. Böhmer, V.: Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. 34, 713 (1995).
18. Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.): Calixarene 2001. Kluwer, Dordrecht (2001).
19. Ikeda, A., Shinkai, S.: Novel cavity design using calix[n]arene skeletons: toward molecular recognition and metal binding. Chem. Rev. 97, 1713-1734 (1997).
20. Sansone, F., Baldini, L., Casnati, A., Lazzarotto, M., Ugozzoli, F., Ungaro, R.: Biomimetic macrocyclic receptors for carboxylate anion recognition based on C-linked peptidocalix[4]arenes. Proc. Natl. Acad. Sci. U. S. A. 99, 4842-4847 (2002).
21. Rebek, J.: Host-guest chemistry of calixarene capsules. Chem. Commun. 8, 637-643 (2000).
22. Lehn, J. M., Meric, R., Vigneron, J. P., Cesario, M., Guilhem, J., Pascard, C., Asfari, Z., Vicens, J.: Binding of acetylcholine and other quaternary ammonium cations by sulfonated calixarenes. Crystal structure of a [choline-tetrasulfonated calix[4]arene] complex. Supramol. Chem 5, 97-103 (1995).
23. Peng, L., Goeldner, M.: Synthesis and characterisation of photolabile choline precursors as reversible inhibitors of cholinesterases: release of choline in the microsecond time range. J. Org. Chem. 61, 185-191 (1996).
24. Peng, L., Silman, I., Sussman, J. L., Goeldner, M.: Biochemical evaluation of photolabile precursors of choline and of carbamylcholine for potential time-resolved crystallographic studies on cholinesterases. Biochemistry 35, 10854-10861 (1996).
25. Specht, A., Goeldner, M.: 1-(o-Nitrophenyl)-2, 2, 2-trifluoroethyl ether derivatives as stable and efficient photoremovable alcohol-protecting groups. Angew. Chem. Int. Ed. 43, 2008-2012 (2004).
26. Peng, L., Nachon, F., Wirz, J., Goeldner, M.: 2-nitrobenzylarsonium compounds that photorelease heavy-atom cholinergic ligands for time-resolved crystallographic studies on cholinesterases. Angew. Chem. Int. Ed. 37, 2691-2693 (1998).
27. Milburn, T., Matsubara, N., Billigton, A. P., Udgaonkar, J. B., Walker, J. W., Carpenter, B. K., Webb, W. W., Marque, J., Denk, W., McCray, J. A., Hess, G. P.: Synthesis, photochemistry, and biological activity of a caged photolabile acetylcholine receptor ligand. Biochemistry. 28, 49-55 (1989).
28. Specht, A., Ziarelli, F., Bernard, P., Goeldner, M., Peng, L.: para-sulfonated calixarenes used as synthetic receptors for complexing photolabile cholinergic ligand. Helv. Chim. Acta. 88, 2641-2653 (2005).
29. Specht, A., Goeldner, M., Wirz, J., Peng, L.: Characterization of caged cholinergic ligand-sulphonated calix[4]arene inclusion complex. Synlett. S1, 981-983 (1999).
30. Specht, A., Bernard, P., Goeldner, M., Peng, L.: Mutually induced formation of host-guest complexes between p-sulfonated calix[8]arene and photolabile cholinergic ligands. Angew. Chem. Int. Ed. Engl. 41, 4706-4708 (2002).
31. Gilson, M. K., Straatsma, T. P., McCammon, J. A., Ripoll, D. R., Faerman, C. H., Axelsen, P. H., Silman, I., Sussman, J. L.: Open back door in a molecular dynamics simulation of acetylcholinesterase. Science. 263, 1276-1278 (1994).
32. Loudwig, S., Goeldner, M.: N-Methyl-N-(o-nitrophenyl)carbamates as photolabile alcohol protecting groups. Tetrahedron Lett. 42, 7957-7959 (2001).
33. Loudwig, S., Nicolet, Y., Masson, P., Fontecilla-Camps, J. C., Bon, S., Nachon, F., Goeldner, M.: Photoreversible inhibition of cholinesterases: catalytic serine-labeled caged butyrylcholinesterase. ChemBioChem. 4, 762-767 (2003).
34. Moffat, K., Ren, Z.: Synchrotron radiation applications to macromolecular crystallography. Curr. Opin. Struct. Biol. 7, 689-696 (1997).
35. Bourgeois, D., Royant, A.: Advances in kinetic protein crystallography. Curr. Opin. Struct. Biol. 15(5), 538-547 (2005).
36. Specht, A., Ursby, T., Weik, M., Peng, L., Bourgeois, D., Goeldner, M.: Cryophotolysis of ortho-nitrobenzyl derivatives of enzyme ligands for the potential kinetic crystallography of macromolecules. ChemBioChem. 2, 845-848 (2001).
37. Ursby, T., Weik, M., Fioravanti, E., Delarue, M., Goeldner, M., Bourgeois, D.: Cryophotolysis of caged compounds: a technique for trapping intermediate states in protein crystals. Acta. Crystallogr. D. Biol. Crystallogr. 58(Pt 4), 607-614 (2002).
38. Colletier, JP., Royant, A., Specht, A., Sanson, B., Nachon, F., Masson, P., Zaccai, G., Sussman, JL., Goeldner, M., Silman, I., Bourgeois, D., Weik, M.: Use of a 'caged' analogue to study the traffic of choline within acetylcholinesterase by kinetic crystallography. Acta. Crystallogr. D. Biol. Crystallogr. 63(Pt 11), 1115-1128 (2007).