Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2007-09-11
2007-09-11
Gitomer, Ralph (Department: 1657)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C544S245000, C546S268400
Reexamination Certificate
active
10053482
ABSTRACT:
A method of measuring the enzymatic activity of a luciferase includes contacting a luminogenic protein, such as a luciferase, with a protected luminophore to form a composition; and detecting light produced from the composition. The protected luminophore provides increased stability and improved signal-to-background ratios relative to the corresponding unmodified coelenterazine.
REFERENCES:
patent: 3958938 (1976-05-01), Doonan et al.
patent: 4080265 (1978-03-01), Antonik
patent: 4349510 (1982-09-01), Kolehmainen et al.
patent: 4501813 (1985-02-01), Lovgren et al.
patent: 4604364 (1986-08-01), Kosak
patent: 4665022 (1987-05-01), Schaeffer et al.
patent: 4806415 (1989-02-01), Fossati
patent: 5023181 (1991-06-01), Inouye
patent: 5035999 (1991-07-01), Geiger et al.
patent: 5098828 (1992-03-01), Geiger et al.
patent: 5246834 (1993-09-01), Tsuji et al.
patent: 5374534 (1994-12-01), Zomer et al.
patent: 5374535 (1994-12-01), Zomer et al.
patent: 5518883 (1996-05-01), Soini
patent: 5541309 (1996-07-01), Prasher
patent: 5587286 (1996-12-01), Pahuski et al.
patent: 5641641 (1997-06-01), Wood
patent: 5648232 (1997-07-01), Squirrell
patent: 5650289 (1997-07-01), Wood
patent: 5650299 (1997-07-01), Lawman et al.
patent: 5700645 (1997-12-01), Pahuski et al.
patent: 5741668 (1998-04-01), Ward et al.
patent: 5770391 (1998-06-01), Foote et al.
patent: 5798263 (1998-08-01), Wood et al.
patent: 5811251 (1998-09-01), Hirose et al.
patent: 5814471 (1998-09-01), Wood
patent: 5831102 (1998-11-01), Bronstein et al.
patent: 5840572 (1998-11-01), Copeland et al.
patent: 5891659 (1999-04-01), Murakami et al.
patent: 5891702 (1999-04-01), Sakakibara et al.
patent: 5908751 (1999-06-01), Higo et al.
patent: 5965453 (1999-10-01), Skiffington et al.
patent: 6004767 (1999-12-01), Crouch et al.
patent: 6007996 (1999-12-01), McNamara et al.
patent: 6133459 (2000-10-01), Schaap et al.
patent: 6165734 (2000-12-01), Garini et al.
patent: 6171809 (2001-01-01), Roelant
patent: 6416960 (2002-07-01), Bryan
patent: 6436682 (2002-08-01), Bryan et al.
patent: WO 01/87853 (2001-11-01), None
patent: 8-294397 (1996-03-01), None
patent: 8-59686 (1996-11-01), None
patent: WO99/66324 (1999-12-01), None
Shimomura, O. “Cause of spectral variation in the luminescence of semisynthetic aequorins”Biochem J.(1995) 306, 537-543.
Nakamura, H. et al. “Design, Synthesis, and Evaluation of the Transition-State Inhibitors of Coelenterazine Bioluminescence: Probing the Chiral Environment of Active Site”J. Am. Chem. Soc.2001, 123, 1523-1524.
International Search Report for corresponding Patent Cooperation Treaty application No. PCT/US02/34972, dated Feb. 11, 2003, 5 pages.
Theodora W. Greene and Peter G. M. Wuts, “Monoprotection of Dicarbonyl Compounds”, in Protective Groups in Organic Synthesis—2ndedition (John Wiley 1991).
Shoji Inoue et al., “Complete Structure ofRenillaLuciferin and Luciferyl Sulfate”, Tetrahedron Letters No. 31, pp. 2685-2688 (1977).
R. Y. Tsien, “A non-disruptive technique for loading calcium buffers and indicators into cells”, Nature, vol. 290, pp. 527-528 (Apr. 9, 1981).
Peter R. Redden et al., “Acyloxymethyl acidic drug derivatives: in vitro hydrolytic reactivity”, International Journal of Pharmaceutics, vol. 180, pp. 151-160 (1999).
Katsunori Teranishi and Osamu Shimomura, “Coelenterazine Analogs as Chemiluminescent Probe for Superoxide Anion”, Analytical Biochemistry 249: pp. 37-43 (1997).
Osamu Shimomura et al., “Semi-synthetic aequorins with improved sensitivity to Ca2+ions”, Biochem. J. 261: pp. 913-920 (1989).
Satoshi Inouye and Osamu Shimomura, “The Use ofRenillaLuciferase,OplophorusLuciferase, and Apoaequorin as Bioluminescent Reporter Protein in the Presence of Coelenterazine Analogues as Substrate”, Biochemical and Biophysical Research Communications 233: 349-353 (1997).
Keith Jones et al., “Glowing jellyfish, luminescence and molecule called coelenterazine”, Tibtech vol. 17, pp. 477-481 (1999).
Osamu Shimomura and Katsunori Teranishi, “Light-emitters involved in thE luminescence of coelenterazine”, Luminescence 15: 51-58 (2000).
Osamu Shimomura et al., “The relative rate of aequorin regulation from apoaequorin and coelenterazine analogues”, Biochem. J. 296: 549-551 (1993).
Osamu Shimomura, “Membrane permeability of coelenterazine analogues measured with fish eggs”, Biochem. J. 326: 297-298 (1997).
“Coelenterazine and Coelenterazine Derivatives”, Molecular Probes—Product Information, pp. 1-3 (Apr. 4, 2000).
“Coelenterazine Sampler Kit”, Molecular Probes—Product Literature, pp. 1-3, (Oct. 16, 2000).
Dubuisson, M. L. et al., “Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress”, Biochem-Pharmacol. 60(4): pp. 471-478 (2000).
Angers, S. et al., “Detection of beta 2-adrenergic receptor dimerization in living cells using bioluminescence resonance energy transfer (BRET)”, Prod. Natl. Acad. Sci. USA 97(7): pp. 3684-3689 (2000).
Liu, J. and Escher, A., “Improved assay sensitivity of an engineered secretedRenillaluciferase”, Gene 237(1): pp. 153-9 (1999).
Srikantha, T. et al., “The sea pansyRenillareniformis luciferase serves as a sensitive bioluminescent reporter for differential gene expression inCandida albicans”, J. Bacteriol. 178(1): pp. 121-129 (1996).
Skarpidi, E. et al., “Novel in vitro assay for the detection of pharmacologic inducers of fetal hemoglobin”, Blood 96(1): pp. 321-326 (2000).
Parsons, S.J. et al., “Use of a dual firefly andRenillaluciferase reporter gene assay to simultaneously determine drug selectivity at human corticotrophin releasing hormone 1 and 2 receptors”, Anal. Biochem. 281(2): pp. 187-192 (2000).
Stables, J. et al., “Development of a dual glow-signal firefly andRenillaluciferase assay reagent for the analysis of G-protein coupled receptor signalling”, J. Recept. Signal Transduct. Res. 19(1-4): pp. 395-410 (1999)—Abstract Only.
Grentzmann, G. et al., “A dual-luciferase reporter system for studying recording signals”, RNA 4(4): pp. 479-486 (1998).
Liu, J. et al, “Visualizing and quantifying protein secretion using aRenillaLuciferase-GFP fusion protein”, luminescence 15(1): pp. 45-49 (2000).
Craig, Frank F. et al. “Membrane-permeable luciferin esters for assay of firefly luciferase in live intact cells” Biochem. J. 276 pp. 637-641 (1991).
Mitani, M. et al Analytical Sciences (1995) 11(6), 1013-1015.
Mitani, M. et al Analytical Sciences (1994) 10(5), 813-814.
Sakaki, H. et al Chem. Abstract No. 1997:48722.
Mitani, M. et al Chem. Abstract No. 1996:335963.
Inoue, S. Chemistry Letters (1987) (2) 417-418.
Inoue, S. Tetrahedron Letters (1977) (31), 2685-8.
Hawkins, E. Bioluminescence & Chemiluminescence: Progress & Current Applications, “Processing of the Symposium on Bioiluminescence and Chemiluminescence,” 12th, Cambridge, United Kingdom, Apr. 5-9, 2002, 149-152. Editor(s) Stanley, Philip, E.; Kricka, Larry, J., 2002, XP008056546.
Supplementary partial European Search Report (Jan. 16, 2006).
Hawkins Erika
Klaubert Dieter
Scurria Mike
Wood Keith
Brinks Hofer Gilson & Lione
Gitomer Ralph
Promega Corporation
LandOfFree
Compounds to co-localize luminophores with luminescent proteins does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Compounds to co-localize luminophores with luminescent proteins, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Compounds to co-localize luminophores with luminescent proteins will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3768582