Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing saccharide radical
Reexamination Certificate
2011-03-22
2011-03-22
Woolwine, Samuel C (Department: 1637)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing compound containing saccharide radical
C435S091200, C536S023100
Reexamination Certificate
active
07910335
ABSTRACT:
The present invention relates to methods for the labeling of nucleic acid polymers in vitro and in vivo. In particular, the methods include a [3+2] cycloaddition between a nucleotide analogue incorporated into a nucleic acid polymer and a reagent attached to a label. Such methods do not require fixation and denaturation and therefore can be applied to the labeling of nucleic acid polymers in living cells and in organisms. Also provided are methods for measuring cellular proliferation. In these methods, the amount of label incorporated into the DNA is measured as an indication of cellular proliferation. The methods of the invention can be used in a wide variety of applications including clinical diagnosis of diseases and disorders in which cellular proliferation is involved, toxicity assays, and as a tool for the study of chromosomes' ultrastructures.
REFERENCES:
patent: 5705622 (1998-01-01), McCapra
patent: 5874532 (1999-02-01), Pieken
patent: 5958696 (1999-09-01), Crute
patent: 6083699 (2000-07-01), Leushner et al.
patent: 6255475 (2001-07-01), Kwiatkowski
patent: 6664047 (2003-12-01), Haughland et al.
patent: 6737236 (2004-05-01), Pieken
patent: 7375234 (2008-05-01), Sharpless
patent: 7427678 (2008-09-01), Pieken
patent: 7763736 (2010-07-01), Sharpless
patent: 2001/0007747 (2001-07-01), Bochkariov et al.
patent: 2003/0171570 (2003-09-01), Schweitzer
patent: 2003/0175728 (2003-09-01), Belousov et al.
patent: 2004/0209317 (2004-10-01), Ting
patent: 2004/0259135 (2004-12-01), Cleary et al.
patent: 2005/0148032 (2005-07-01), Saxon et al.
patent: 2006/0147963 (2006-07-01), Barone et al.
patent: 2007/0099222 (2007-05-01), Gee et al.
patent: 2008/0199872 (2008-08-01), Barnard et al.
patent: 2008/0268462 (2008-10-01), Kosmeder et al.
patent: 2009/0215635 (2009-08-01), Carell
patent: WO-89/02475 (1989-03-01), None
patent: WO-96/09316 (1996-03-01), None
patent: WO-96/20289 (1996-07-01), None
patent: WO-96/34984 (1996-11-01), None
patent: WO-98/30575 (1998-07-01), None
patent: WO-02/29003 (2002-04-01), None
patent: WO-03/101972 (2003-12-01), None
patent: WO-2004/018497 (2004-03-01), None
patent: WO-2006/038184 (2006-04-01), None
patent: WO-2006/116629 (2006-11-01), None
patent: WO-2006/117161 (2006-11-01), None
Seo et al. Click chemistry to construct fluorescent oligonucleotides for DNA sequencing. J. Org. Chem 68:609-612 (2003).
Mao et al. Profound astrogenesis in the striatum of adult mice following nigrostriatal dopaminergic lesion by repeated MPTP administration. Developmental Brain Research 131:57-65 (2001).
Gallo et al. Oligodendrocyte progenitor cell proliferation and lineage progression are regulated by glutamate receptor-mediated K+ channel block. Journa of Neuroscience 16(8):2659-2670 (1996).
Van Rompay et al. Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases. Pharmacology & Therapeutics 87:189-198 (2000).
De Clercq, E. Antiviral activity of 5-substituted pyrimidine nucleoside analogues. Pure & Applied Chemistry 55(4):623-636 (1983).
De Clercq et al. Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 2′-deoxyuridines on mouse leukemia L1210 cell growth. Molecular Pharmacology 19:321-330 (1981).
Summerer et al. 4′C-ethynyl-thymidine acts as a chain terminator during DNA-synthesis catalyzed by HIV-1 reverse transcriptase. Bioorganic & Medicinal Chemistry Letters 15:869-871 (Jan. 19, 2005).
Akerblom, L. Azidocytidine is incorporated into RNA of 3T6 mouse fibroblasts. FEBS Letters 193(2):203-207 (1985).
Agard et al., “A Strain-Promoted [3+2] Azide-Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems”,J. Am. Chem. Soc., 2004, 126: 15046-15047.
Aguilera et al., “Permeabilizing action of an antimicrobial lactoferricin-derived peptide on bacterial and artificial membranes”,FEBS Lett.1999, 462: 273-277.
Bergstrom and J.L. Ruth, “Letter: Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates”,J. Am. Chem. Soc., 1976, 98: 1587-1589.
Beutler, “Cladribine (2-chlorodeoxyadenosine)”,Lancet, 1992, 340: 952-956.
Bleackley et al., “The preparation of 5-cyanouracil and 5-cyano-2′-deoxyuridine from the corresponding 5-iodo derivative and cuprous cyanide”,Nucleic Acids Res., 1975, 2: 683-690.
Bussing et al., “Expression of mitochondrial Apo2.7 molecules and caspase-3 activation in human lymphocytes treated with the ribosome-inhibiting mistletoe lectins and the cell membrane permeabilizing viscotoxins”,Cytometry, 1999, 37: 133-139.
Goncalves et al., “The use of permeabilized cells to assay protein phosphorylation and catecholamine release”,Neurochem. Res.2000, 25: 885-894.
He et al., “Synthesis of 5-substituted 2′-deoxycytidine 5′-(alpha-P-borano)triphosphates, their incorporationinto DNA and effects on exonuclease”,Nucleic Acids Res., 1999, 8:1788-1798.
Held and Benner, “Challenging artificial genetic systems: thymidine analogs with 5-position sulfur functionality”,Nucleic Acids Res., 2002, 30: 3857-3869.
Hellerstein et al., “Directly measured kinetics of circulating T lymphocytes in normal and HIV-1-infected humans”,Nature Med., 1999, 5: 83-89.
Hellerstein, “Measurement of T-cell kinetics: recent methodologic advances”,Immunol. Today, 1999, 20: 438-441.
Hui and Reitz, “Gemcitabine: a cytidine analogue active against solid tumors”,Am. J. Health-Syst. Pharm., 1997, 54: 162-170.
Iwasaki et al., “Differential incorporation of ara-C, gemcitabine, and fludarabine into replicating and repairing DNA in proliferating human leukemia cells.”,Blood, 1997, 90: 270-278.
Jones et al., “A method for the rapid preparation of 5-vinyluracil in high yield”,Nucleic Acids Res., 1974, 1: 105-107.
Kanda et al., “Histone-GFP fusion protein enables sensitive analysis of chromosome dynamics in living mammalian cells”,Curr. Biol., 1998, 8: 377-385.
Kufe et al., “Relationships among Ara-CTP pools, formation of (Ara-C)DNA, and cytotoxicity of human leukemic cells”,Blood, 1984, 64: 54-58.
Lewis et al., “Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks”,Angew Chem. Int. Ed. Engl., 2002, 41: 1053-1057.
Macallan et al., “Measurement of cell proliferation by labeling of DNA with stable isotope-labeled glucose: studies in vitro, in animals, and in humans”,Proc. Natl. Acad. Sci. USA, 1998, 95: 708-713.
Maranto, “Neuronal mapping: a photooxidation reaction makes Lucifer yellow useful for electron microscopy”,Science, 1982, 217: 953-955.
Mutasa, “Osmium tetroxide-potassium ferrocyanide intensification of a diaminobenzidine product obtained by photoconversion of a fluorescent label: a study of human neutrophil granules”,Biotech. Histochem., 1995, 70: 194-201.
Ribeiro et al., “Modeling deuterated glucose labeling of T-lymphocytes”,Bull. Math. Biol., 2002, 64: 385-405.
Rostovtsev et al., “A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and.terminal alkynes”,Angew Chem., Int. Ed. Engl., 2002, 41: 2596-2599.
Shealy et al., Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity,J. Med. Chem., 1983, 26: 156-161.
Sunthankar et al., “Synthesis of 5-azido-UDP-N-acetylhexosamine photoaffinity analogs and radiolabeled UDP-N-acetylhexosamines”,Anal. Biochem., 1998, 258: 195-201.
Van de Bor and I. Davis, “mRNA localisation gets more complex”,Curr. Opin. Cell Biol., 2004, 16: 300-307.
Wang et al., “Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition”,J. Am. Chem. Soc., 2003, 125: 3192-3193.
U.S. Appl. No. 11/588,697, filed Oct. 27, 2006, Salic et al.
Chen, I., “Site-specific labeling of p
Mitchison Timothy J.
Salic Adrian
Choate Hall & Stewart LLP
Huck Emilie Porter
Life Technologies Corporation
Lyon Charles E.
President and Fellows of Harvard College
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