Synthesis and photolytic evaluation of a nitroindoline-caged glycine with a side chain of high negative charge for use in neuroscience

Tetrahedron

Volumn 67, Issue 29, 2011, Pages 5228-5234

  Papageorgiou, George ^a   Beato, Marco ^b   Ogden, David ^c  

^a NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c CNRS   (France)

Author keywords

Caged compounds; Nitroindolines; Phosphorylation; Photolysis

Indexed keywords

1 (2 AMINOACETYL) 4 [1,3 BIS(DIHYDROXYPHOSPHORYLOXY)PROPAN 2 YLOXY] 7 NITROINDOLIN; 1 (2 AZIDOACETYL) 4 (1,3 DIACETOXYPROPAN 2 YLOXY) 7 NITROINDOLINE; 1 (2 AZIDOACETYL) 4 (1,3 DIACETOXYPROPAN 2 YLOXY)INDOLINE; 1 (2 AZIDOACETYL) 4 (1,3 DIHYDROXYPROPAN 2 YLOXY)INDOLINE; 1 (2 AZIDOACETYL) 4 [1,3 BIS(DI TERT BUTOXYPHOSPHORYLOXY)PROPAN 2 YLOXY]INDOLINE; 1 (2 AZIDOACETYL) 4 [1,3 BIS(DIHYDROXYPHOSPHORYLOXY)PROPAN 2 YLOXY] 7 NITROINDOLINE; 1 (2 BROMOACETYL) 4 (1,3 DIACETOXYPROPAN 2 YLOXY)INDOLINE; 1 ACYL 7 NITROINDOLINE DERIVATIVE; 4 AMINOBUTYRIC ACID; GLYCINE; INDOLE DERIVATIVE; NITROINDOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; NEUROSCIENCE; PRIORITY JOURNAL; SYNTHESIS;

EID: 79958770247     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.045     Document Type: Article

References (33)

1. (a) Corrie, J. E. T. In Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules; Goeldner, M., Givens, R., Eds.; Wiley VCH: Weinheim, 2005; pp 1-28;
2. (b) Adams, S. R.; Tsien, R. Y. Annu. Rev. Physiol. 1993, 55, 755-784;
3. (c) Kaplan, J. H. Annu. Rev. Physiol. 1990, 52, 897-914;
4. (d) Methods in Enzymology; Marriott, G., Ed.; Academic: New York, NY, 1998; Vol. 291;
5. (e) Pelliccioli, A.; Wirz, J. Photochem. Photobiol. Sci. 2002, 1, 441-458.
6. Papageorgiou, G.; Ogden, D. C.; Barth, A.; Corrie, J. E. T. J. Am. Chem. Soc. 1999, 121, 6503-6504.
7. (a) Papageorgiou, G.; Corrie, J. E. T. Tetrahedron 2000, 56, 8197-8205;
8. (b) Papageorgiou, G.; Corrie, J. E. T. Synth. Commun. 2002, 32, 1571-1577.
9. Canepari, M.; Nelson, L.; Papageorgiou, G.; Corrie, J. E. T.; Ogden, D. J. Neurosci. Methods 2001, 112, 29-42.
10. Maier, W.; Corrie, J. E. T.; Papageorgiou, G.; Laube, B.; Grewer, C. J. Neurosci. Methods 2005, 142, 1-9.
11. Zhang, Z.; Papageorgiou, G.; Corrie, J. E. T.; Grewer, C. Biochemistry 2007, 46, 3872-3880.
12. Canepari, M.; Papageorgiou, G.; Corrie, J. E. T.; Watkins, C.; Ogden, D. J. Physiol. 2001, 533, 756-772.
13. (a) Matsuzaki, M.; Ellis-Davies, G. C. R.; Nemoto, T.; Miyashita, Y.; Iino, M.; Kasai, M. Nat. Neurosci. 2001, 4, 1086-1092;
14. (b) Smith, M. A.; Ellis-Davies, G. C. R.; Magee, J. C. J. Physiol. 2003, 548, 245-258;
15. (c) Canepari, M.; Ogden, D. J. Neurosci. 2003, 23, 4066-4071;
16. (d) Lowe, G. J. Neurophysiol. 2003, 90, 1737-1746;
17. (e) Shepherd, G. M. G.; Pologruto, T. A.; Svoboda, K. Neuron 2003, 38, 277-289;
18. (f) Canepari, M.; Auger, C.; Ogden, D. J. Neurosci. 2004, 24, 3563-3573;
19. (g) Matsuzaki, M.; Honkura, N.; Ellis-Davies, G. C. R.; Kasai, H. Nature 2004, 429, 761-766;
20. (h) Carter, A. G.; Sabatini, B. L. Neuron 2004, 44, 483-493;
21. (i) Bureau, I.; Shepherd, G. M. G.; Svoboda, K. Neuron 2004, 42, 789-801;
22. (j) Huang, Y. H. H.; Sinha, S. R.; Fedoryak, O. D.; Ellis-Davies, G. C. R.; Bergles, D. E. Biochemistry 2005, 44, 3316-3326;
23. (k) Bloodgood, B. L.; Sabatini, B. Science 2006, 310, 866-869;
24. (l) Canepari, M.; Ogden, D. J. Physiol. 2006, 573, 65-82.
25. Morrison, J.; Wan, P.; Corrie, J. E. T.; Papageorgiou, G. Photochem. Photobiol. Sci. 2002, 1, 960-969.
26. Papageorgiou, G.; Corrie, J. E. T. Tetrahedron 2007, 63, 9668-9676.
27. (a) Trigo, F. F.; Papageorgiou, G.; Corrie, J. E. T.; Ogden, D. J. Neurosci. Methods 2009, 181, 159-169;
28. (b) Trigo, F. F.; Bouhours, B.; Rostaing, P.; Papageorgiou, G.; Corrie, J. E. T.; Triller, A.; Ogden, D.; Marty, A. Neuron 2010, 66, 235-247.
29. Ueno, S.; Nabekura, J.; Ishbashi, H.; Akaike, N.; Mori, M.; Shiga, M. J. Neurosci. Methods 1995, 58, 163-166.
30. Papageorgiou, G.; Ogden, D.; Corrie, J. E. T. J. Org. Chem. 2004, 69, 7228-7233.
31. Kawada, A.; Takeda, S.; Yamashita, K.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 2002, 50, 1060-1065.
32. (a) Sangvi, S. Y.; Guo, Z.; Pfundheller, H. M.; Converso, A. Org. Process Res. Dev. 2000, 4, 175-181;
33. (b) Zhang, Y.; Heisen, M. H.; Kostic, M.; Pagani, G. M.; Riera, T. V.; Perovic, I.; Hedstrom, L.; Snider, B. B.; Pochapsky, T. C. Bioorg. Med. Chem. 2004, 12, 3847-3855.