An antenna-sensitised 1-acyl-7-nitroindoline that has good solubility properties in the presence of calcium ions and is suitable for use as a caged l-glutamate in neuroscience

Photochemical and Photobiological Sciences

Volumn 7, Issue 4, 2008, Pages 423-432

  Papageorgiou, George ^a   Ogden, David ^b   Corrie, John E T ^a  

^a NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACYL 7 NITROINDOLINE; BENZOPHENONE; CALCIUM ION; DICARBOXYLIC ACID; GLUTAMIC ACID; INDOLE DERIVATIVE; PHOSPHATE; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ANTENNA; ARTICLE; CHEMOSENSITIZATION; MENTAL INSTABILITY; NEUROSCIENCE; NONHUMAN; PHOTOLYSIS; PRECIPITATION; PRIORITY JOURNAL; RAT; SOLUBILITY; STOICHIOMETRY; SYNTHESIS;

EID: 41749103096     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b800683k     Document Type: Article

References (25)

1. G. Papageorgiou D. C. Ogden A. Barth J. E. T. Corrie Photorelease of carboxylic acids from 1-acyl-7-nitroindolines in aqueous solution: rapid and efficient photorelease of l-glutamate J. Am. Chem. Soc. 1999 121 6503 6504
2. G. Papageorgiou J. E. T. Corrie Effects of aromatic substitution on the photocleavage of 1-acyl-7-nitroindolines Tetrahedron 2000 56 8197 8205
3. J. Morrison P. Wan J. E. T. Corrie G. Papageorgiou Mechanisms of photorelease of carboxylic acids from 1-acyl-7-nitroindolines in solutions of varying water content Photochem. Photobiol. Sci. 2002 1 960 969
4. G. Papageorgiou J. E. T. Corrie Synthesis of an anionically-substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors Tetrahedron 2007 63 9668 9676
5. G. Papageorgiou M. Lukeman P. Wan J. E. T. Corrie An antenna triplet sensitiser for 1-acyl-7-nitroindolines improves the efficiency of carboxylic acid photorelease Photochem. Photobiol. Sci. 2004 3 366 373
6. G. Papageorgiou D. Ogden J. E. T. Corrie An antenna-sensitized nitroindoline precursor to enable photorelease of l-glutamate in high concentrations J. Org. Chem. 2004 69 7228 7233
7. G. Papageorgiou J. E. T. Corrie Optimised synthesis and photochemistry of antenna-sensitised 1-acyl-7-nitroindolines Tetrahedron 2005 61 609 616
8. D. Ogden, unpublished data
9. M. Canepari L. Nelson G. Papageorgiou J. E. T. Corrie D. Ogden Photochemical and pharmacological evaluation of 7-nitroindolinyl and 4-methoxy-7-nitroindolinyl-caged neurotransmitters for use in neurophysiology J. Neurosci. Methods 2001 112 29 42
10. M. Matsuzaki G. C. R. Ellis-Davies T. Nemoto Y. Miyashita M. Iino M. Kasai Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons Nat. Neurosci. 2001 4 1086 1092
11. 2+ ion permeability and single-channel properties of the metabotropic slow EPSC of rat Purkinje neurons J. Neurosci. 2004 24 3563 3573
12. T. Wharton L. J. Wilson Highly-iodinated fullerene as a contrast agent for X-ray imaging Bioorg. Med. Chem. 2002 10 3545 3555
13. L. L. Costanzo G. DeGuidi G. Conderelli A. Cambria M. Fama Molecular mechanism of drug photosensitization. 2. Photohemolysis sensitized by ketoprofen Photochem. Photobiol. 1989 50 359 365
14. G. L. Hug M. Bonifačić K. D. Asmus D. A. Armstrong Fast decarboxylation of aliphatic amino acids induced by 4-carboxybenzophenone triplets in aqueous solution. A nanosecond laser flash photolysis study J. Phys. Chem. B 2000 104 6674 6682
15. R. S. Davidson P. R. Steiner Photosensitized decarboxylation of carboxylic acids by benzophenone and quinones J. Chem. Soc. C 1971 1682 1689
16. J. Maylie M. Irving N. L. Sizto G. Boyarski W. K. Chandler Calcium signals recorded from cut frog twitch fibers containing tetramethylmurexide J. Gen. Physiol. 1987 89 145 176
17. A. Barth S. R. Martin J. E. T. Corrie Decarboxylation is a significant reaction pathway for photolabile calcium chelators and related compounds Photochem. Photobiol. Sci. 2006 5 107 115
18. J. E. T. Corrie V. R. N. Munasinghe D. R. Trentham A. Barth Studies of decarboxylation in photolysis of α-carboxy-2-nitrobenzyl (CNB) caged compounds Photochem. Photobiol. Sci. 2008 7 84 97
19. V. Jayaraman S. Thiran D. R. Madden Fourier transform infrared spectroscopic characterization of a photolabile precursor of glutamate FEBS Lett. 2000 475 278 282
20. 15N isotopomers of a 1-acyl-7-nitroindoline J. Labelled Compd. Radiopharm. 2001 44 619 626
21. H. W. Thompson R. W. Needham D. Jameson The intensities of the carbonyl group vibration in some aromatic compounds Spectrochim. Acta 1957 9 208 215
22. J. W. Walker G. P. Reid J. A. McCray D. R. Trentham Photolabile 1-(2-nitrophenyl)ethyl phosphate esters of adenine nucleotide analogues. Synthesis and mechanism of photolysis J. Am. Chem. Soc. 1988 110 7170 7177
23. A. Barth J. E. T. Corrie M. J. Gradwell Y. Maeda W. Mäntele T. Meier D. R. Trentham Time-resolved infrared spectroscopy of intermediates and products from photolysis of 1-(2-nitrophenyl)ethyl phosphates: reaction of the 2-nitrosoacetophenone by-product with thiols J. Am. Chem. Soc. 1997 119 4149 4159
24. B. Diepold P. Eyer H. Kampffmeyer K. Reinhardt Reactions of aromatic nitroso compounds with thiols Adv. Exp. Med. Biol. 1982 136B 1173 1181
25. F. Troxler G. Bormann F. Seeman Synthesen von Mannich-Basen von Hydroxy-indolen. 3. Mitteilung über synthetische Indol-Verbindungen Helv. Chim. Acta 1968 51 1203 1213