Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2011-03-01
2011-03-01
Kosack, Joseph R. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S410000, C548S421000, C549S460000, C549S461000
Reexamination Certificate
active
07897638
ABSTRACT:
Inventors have developed a chromophore (nitrodibenzylfuranyl, or NBDF) for ultra efficient uncaging of a caged substrate (e.g., an organic molecule such as, for example, an amino acid, a biological molecules, such as, for example, second messengers inside cells). Photolysis of a NBDF derivative of EGTA (i.e. caged calcium) is about 50 times more efficient than others calcium cages (the quantum yield of photolysis is 0.6 and the extinction coefficient is 18,400. NDBF-EGTA has a 2-photon cross section of about 0.3-0.6 GM).
REFERENCES:
patent: 4981985 (1991-01-01), Kaplan et al.
patent: 5034613 (1991-07-01), Denk et al.
patent: 5430175 (1995-07-01), Hess et al.
patent: 5446186 (1995-08-01), Ellis-Davies et al.
patent: 5498765 (1996-03-01), Carpenter et al.
patent: 5587509 (1996-12-01), Hess et al.
patent: WO2004085394 (2004-10-01), None
Keumi et al. J. Org. Chem. 1991, 56, 4671-4677.
Merriam-Webster Online Dictionary entry for “derivative”, (http://www.merriam-webster.com/dictionary/derivative), last accessed May 12, 2010.
Momotake et al. Nature Methods, 2006, 3, 35-40.
Kaplan, J. H. (1990) Annu. Rev. Physiol. 52, 897-914.
Adams, S. R., Kao, J. P. Y., Grynkiewicz, G., Minta, A., & Tsien, R. Y. (1988) J. Am. Chem. Soc. 110, 3212-3220.
Keumi, T., J. Org. Chem. (1991) vol. 56, pp. 4671-4677.
Wieboldt, R., Gee, K.Y., Niu, L., Ramash, D., Carpenter, B.K., and Hess, G.P. (1994b) “Photolabile presurors of glutamate: Synthesis, photochemical properties, activation of glutamate receptors in the microsecond time scale.”Proc. Natl. Acad. Sci. (USA) (1994) vol. 91, pp. 8752-8756).
Patchornik A., J. Am. Chem. Soc. (1970) vol. 92, pp. 6333-6335).
Jasuja, et al., Biophysical Journal (1999) vol. 76, pp. 1706-1719.
Brewster, Organic Syntheses Collected vol. 2. pp. 445-446.
Ellis-Davies G.C.R. , (2005) in Imaging in Neuroscience and Development (Eds.: R. Yuste, A. Konnerth), Cold Spring Harbor Laboratory Press, Cold Spring Harbor, 2005, 367-374.
Corrie, J.E.T. et al., (1993) “Caged nucleotides and neurotransmitters” In Bioorganic Photochemistry 2 (ed. H. Morrison) John Wiley and Son, New York, pp. 243-305.
Corrie J.E.T., (2005) “Photoremovable Protecting Groups Used for the Caging of Biomolecules” in Dynamic Studies in Biology (eds Maurice Goeldner (Editor), Richard Givens) Wiley.
Ellis-Davies G.C.R et al., (1994) “Nitrophenyl-EGTA, a photolabile chelator that selectively binds Ca2+ with high affinity and releases it rapidly upon photolysis” Proc. Natl. Acad. Sci. USA, 91: 187-191.
Ellis-Davies G.C.R et al., A new class of photolabile chelators for the rapid release of divalent cations: generation of caged Ca and caged Mg. J. Org. Chem. 53 (1988) 1966-1969.
Kaplan et al., Photolabile chelators for the rapid photorelease of divalent cations Proc. Natl. Acda. Sci. (USA) 85 (1988) 6571-6575.
Ellis-Davies G.C.R, Synthesis of photolabile EGTA derivatives. Tetrahedron Lett. 39 (1998) 953-957.
Matsuzaki M. et al., Dendritic spine morphology is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons, Nature Neuroscience 2001, 4, 1086-1092.
Adams S.R. et al., A new caged Ca2+, azid-1, is far more photosensitive than nitrobenzyl-based chelators. Chem & Biol. 4 (1997) 867-878.
Tsien R.Y. et al., Control of cytoplasmic calcium with photoabile tetracaroxylate 2-nitrobenhydrol chelators. Biophys. J. 50 (1986) 843-853.
Adams S.R. et al., Biologically useful chelators that release Ca2+ upon illumination. J. Am. Chem. Soc. 110 (1998) 3212-3220.
Kantevari S. et al., Synthesis and 2-photon photolysis of 6-(ortho-nitroveratryl)-caged IP3, ChemBioChem. 2006, 7, 174-182.
Engert F et al., A low cost UV laser for flash photolysis of caged compounds, J. Neurosci. Methods. 1996 66, 47-54.
Engels J. et al., Synthesis, structure and reactivity of adenosine cyclic 3′,5′-phosphate benzyl triesters, J. Med. Chem. 20, 907-911 (1977).
Kishimoto T. et al., Ion selectivities of the Ca2+ sensors for exocytosis in rat phaeochromocytoma cells., J. Physiol. 2001, 533, 627-637.
Delprincipe F. et al., Two-photon and UV-laser Flash Photolysis of the Ca2+ Cage, Dimethoxynitrophenyl-EGTA-4., Cell Calcium 1999, 25, 85-95.
Lipp P. et al., Fundamental calcium release events revealed by two-photon photolysis of caged calcium in guinea-pig cardiac myocytes., J. Physiol. 508 801-809 (1998).
Denk et al., Two-photon laser scanning fluorescence microscopy. Science 248, 73-76 (1990).
Denk, Two-photon scanning photochemical microscopy: mapping ligand-gated ion channel distributions., Proc. Natl. Acad. Sci. U. S. A. 1994, 91: 6629-6633.
Denk et al., Photo upmanship: why multiphoton imaging is more than a gimmick. Neuron 18, 351-357 (1997).
International Search Report for PCT/US2006/013634, 2006.
Ellis-Davies Graham
Momotake Atsuya
Caesar Rivise Bernstein Cohen & Pokotilow Ltd.
Coughlin Matthew P
Kosack Joseph R.
Philadelphia Health & Education Corporation
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