Uridine analogs and techniques for making and using

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S026100, C536S026200, C536S026210, C536S026800, C536S028400, C536S028540, C536S124000

Reexamination Certificate

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06987180

ABSTRACT:
Uridine analogs and techniques for making and using uridine analogs are disclosed in this invention. These uridine analogs include nucleoside phosphates having a 5-aminouracil group. These nucleotides can be incorporated into a nucleic acid as an unnatural base, as a substitute for uridine or thymine. The nucleic acid can then be treated with an oxidizing agent and an alkaline solution, which causes cleavage of the nucleic acid at the position of the unnatural base. The nucleoside phosphate analogs can be used in many ways, including measuring chemical interactions between nucleic acids and other compounds, or sequencing nucleic acids. Additional compounds can also be derivitized onto the amino group, allowing other functionalities to be added to the nucleoside phosphate, or to the nucleic acid incorporating the nucleoside phosphate.

REFERENCES:
patent: 4672111 (1987-06-01), Haley et al.
patent: 4983727 (1991-01-01), Bergstrom et al.
patent: 5215882 (1993-06-01), Bahl et al.
patent: 5241060 (1993-08-01), Engelhardt et al.
patent: 137 110 (1979-08-01), None
patent: WO 98/00433 (1998-01-01), None
patent: WO 99/08110 (1999-02-01), None
patent: WO 00/18967 (2000-04-01), None
patent: WO 01/07087 (2001-02-01), None
patent: WO 01/07088 (2001-02-01), None
Ferrer et al., “Preparation of Oligonucleotides Containing 5-Bromouracil and 5-Methyolcytidine”,Nucleosides&Nucleotides, vol. 15, No. 4, 1996, pp. 907-921.
Desgranges et al., “Phosphorolysis of )E)-5-(2-Bromovinyl)-2′-Deoxyuridine (BVDU) and Other 5-Substituted-2′-Deoxyuridines by Purified Human Thymidine Phosphorylase and Intact Blood Platelets”,Biochemical Pharmacology, vol. 32, No. 23, 1983, pp. 3583-3590.
Roy-Burman, et al., “Studies on the Effect of Triphosphates of 5-Aminouridine and 5-Hydroxydeoxyuridine of Ribonucleic Acid and Deoxyribonucleic Acid Polymerases”,Biochemical Pharmacolog, vol. 19, 1970, pp. 2745-2756.
Leunget al., “ Characteristics of Deoxythymidine Transport and Deoxythymidine Kinase in 3T3 Cells”,Biochemical Medicine, vol. 16, 1976, pp. 127-137.
Cinatl et al., “2′,3′-Dideoxycytidine Preferentially Inhibits in vitro Growth of Granulocyte-Macrophage Colony-Forming Cells from Patients with Chronic Myeloid Leukemia”,Chemotherapy, vol. 37, 1991, pp. 128-133.
Balzarini et al., “5-Substituted 2′-Deoxyuridines: Correlation Between Inhibition of Tumor Cell Growth and Inhibition of Thymidine Kinase and Thymidylate Synthetase”,Biochemical Pharmacoloy, vol. 31, No. 22, 1982, pp. 3673-3682.
Barawkar et al., “Solid Phase Synthesis of DNA Containing 5-NH2-2′-Deoxyuridine”,Bioorg. Med. Chem. Lett., vol. 3, 1993, pp. 347-352.
Cheng et al., “Mouse Ascites Sarcoma 180 Deoxythymidine Kinase. General Properties and Inhibition Studies”,Biochemistry, vol. 13, No. 6, 1974, pp. 1179-1185.
Eriksson et al., “Comparison of the Substrate Specificities of Human Thymidine Kinase 1 and 2 and Deoxycytidine Kinase Toward Antiviral and Cytostatic Nucleoside Analogs”,Biochemical and Biophysical Research Communications, vol. 176, No. 2, 1991, pp. 586-592.
Ferrer et al., “Preparation and Properties of Oligodeoxynucleotides Containing 5-Iodouracil and 5-Bromo-and 5-lodocytosine”,Bionconjugate Chem., vol. 8, No. 5, 1997, pp. 757-761.
Hampton et al., Design of Species- or Isozyme-Specific Enzyme Inhibitors. 2. Differences between a Bacterial and a Mammalian Thymidine Kinase in the Effect of Thymidine Substituents on Affinity for the Thymidine Site,J. Med. Chem., vol. 22, No. 12, 1979, pp. 1524-1528.
Hampton et al., “Design of Species- or Isozyme-Specific Enzyme Inhibitors. 1. Effect of Thymdine Substituents on Affinity for the Thymidine Site of Hamster Cytoplasmic Thymidine Kinase”,J. Med. Chem. Soc., vol. 22, No. 6, 1979, pp. 621-631.
Hampton et al., “Species- or Isozyme-Specific Enzyme Inhibitors. 5. Differential Effects of Thymidine Substituents on Affinity for Rat Thymidine Kinase Isozymes”,J. Med. Chem., vol. 25, No. 6, 1982, pp. 644-649.
Hayashibara et al., “Template-Directed Interference Footprinting of Cytosine Contacts in a Protein-DNA Complex: Potent Interference by 5-Aza-2′-deoxycytidine”,Biochemistry, vol. 31, No. 46, 1992, pp. 11265-11273.
Hayashibara et al., “Template-Directed Interference Footprinting of Protein-Guanine Contacts in DNA”,J. Am. Chem. Soc., vol. 113, No. 13, 1991, pp. 5104-5106.
Lee et al., “Human Deoxythymidine Kinase II: Substrate Specificity and Kinetic Behavior of the Cytoplasmic and Mitochondrial Isozymes Derived from Blast Cells of Acute Myelocytic Leukemia”,Biochemistry, vol. 15, No. 17, 1976, pp. 3686-3690.
Mascarenas et al., “Template-Directed Interference Footprinting of Protein-Thymine Contacts”,J. Med. Chem. Soc., vol. 115, No. 1, 1993, pp. 373-374.
Wigerinck et al., “Synthesis and Antiviral Activity of 5-Heteroaryl-Substituted 2′-Deoxyuridines”,J. Med. Chem., vol. 34, No. 6, 1991, pp. 1767-1772.
Barawkar et al., “Effect of C5-Amino Substituent on 2′-Deoxyuridine base pairing with 2′-Deoxyadenosine: Investigation by H and C NMR Spectroscopy”,Tetrahedron, vol. 48, No. 39, 1992, pp. 8505-8514.
Evans et al. “Synthesis and Biological Properties of 5-Azido-2′-deoxyuridine 5′-Triphosphate, a Photoactive Nucleotide Suitable for Making Light-Sensitive DNA”,Biochemistry, vol. 26, No. 1, 1987, pp. 269-276.
Evans et al., “5-Azido-2′-deoxyuridine 5′-triphosphate: A photoaffinity-labeling reagent and tool for the enzymatic synthesis of photoactive DNA”,Proc. Natl. Acad. Sci. USA, vol. 83, 1986, pp. 5382-5386.
Kumar et al., “Nonradioactive Labeling of Synthetic Oligonucleotide Probes with Terminal Deoxynucleotidyl Transferase”,Analytical Biochemistry, vol. 169, 1988, pp. 376-382.
Jadhav et al., “5-Amido-(Carboxyfluorescein)-2′-dU-Oligonucleotides: Novel Primers for Fluorescent Detection of PCR Amplified DNA”,Nucleosides&Nucleotides, vol. 16, No. 1&2, 1997, pp. 107-114.
Dyatkina et al, “Terminating substrates of DNA polymerases: synthesis and functional study”,Symposium Series, No. 8, 1987, pp. 117-120.
Beck et al., “Enhancement of Methotrexate Cytotoxicity by Uracil Analogues that Inhibit Deoxyuridine Triphosphate Nucleotidohydrolase (duTPhase) Activity”,Adv. Ext. Med. Biol., vol. 195B, 1996, pp. 97-104.
Balzarini et al., “Strucutre-Function Relationship of the Antitumor Cell Activity of Pyrimidine and Pyradine Derivatives”,Proc. Int. Roundtable Nucleosides, Nucleosides Bio. Appl., vol. 4, 1982, pp. 275-291.
Barawkar et al., “Effect of C5-amino substituent on 2′-deoxyuridine base pairing with 2′-deoxyadenosine: Investigation by H and C NMR spectroscopy”,Tetrahedron, vol. 48, No. 39, 1992, pp. 8505-8514.

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