Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2005-01-18
2005-01-18
Wilson, James O. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S307000, C514S314000, C514S339000, C514S374000, C514S422000, C514S432000, C514S538000, C424S001650, C435S018000, C536S017200, C536S017300, C536S017400, C536S017700, C536S017800, C536S017900, C536S018100, C536S018400
Reexamination Certificate
active
06844346
ABSTRACT:
The subject invention discloses materials and methods for the design, synthesis, and biochemical evaluation of chromogenic substrate compounds for sialidases of bacterial, viral, protozoa, and vertebrate (including humans) origin. These compounds are based upon N-acetylneuraminic acid glycosides. In particular, this invention provides a novel class of these compounds as chromogenic substrates of these sialidases which yield chromogenic products after reactions catalyzed by sialidase take place. Also provided are methods of making these substrate compounds, methods of diagnosis and prognosis of sialidase related diseases using these substrate compounds.
REFERENCES:
patent: 3950322 (1976-04-01), Thomas et al.
patent: 4318986 (1982-03-01), Richardson et al.
patent: 4351823 (1982-09-01), Rubin
patent: 4994376 (1991-02-01), Zambon et al.
patent: 5663055 (1997-09-01), Turner et al.
patent: 6512100 (2003-01-01), Johnson et al.
patent: 0413561 (1991-02-01), None
patent: 2008103 (1979-05-01), None
patent: 02088594 (1990-03-01), None
patent: 05339283 (1993-12-01), None
patent: 06067956 (1994-08-01), None
patent: 8902473 (1989-03-01), None
patent: 9109975 (1990-12-01), None
patent: 9212256 (1992-07-01), None
patent: 0024753 (2000-05-01), None
Hirst, G.K. (1941) “The Agglutination of Red Blood Cells by Allontoic Fluid of Chick Embryos Infected with Influenza Virus” Science 94(2427):22-23.
Gornati, Rosalba, Subhash Basu, Giovanni Bernardini, Angela M. Rizzo, Federica Rossi, Bruno Berra (1997) “Activities of flycolipid glycosyltransferases and sialidases during the early development ofXenopus Iaevis” 166:117-124.
Cacalano, Grace, Maureen Kays, Lisa Salman, Alice Prince (1992) “Production of thePseudomonas aeruginosaNeuraminidase is increased under Hyperosmolar Conditions and is Regulated by Genes involved in Alginate Expression” J. Clin. Invest. 891866-1874.
Bratosin et al. (1995) “Flow cytofluorimetric analysis of young and senescent human erythrocytes probed with lectins. Evidence that sialic acids control their life span” Glycoconjugate Journal 12:258-267.
Liu, Chongguang, Maryna C. Eichelberger, Richard W. Compans, Gillian M. Air (1995) “Influenza Type A Virus Neuraminidase Does Not Play A Role in Viral Entry, Replication, Assembly, or Budding” Journal of Virology 69(2):1099-1106.
Liljemark, William F., Cynthia G. Bloomquist, Laurie J. Fenner, Patrick J. Antonelli, M. Cecilia Coulter (1989) “Effect of Neuraminidase on the Adherence to Salivary Pellicle ofStreptococcus sanguisandStreptococcus mitis” Caries Res. 23:141-145.
Ashwell et al. (1992) “Pathways for the hydrolysis of glycosides of N-acetylneuraminic acid”J. Am. Chem. Soc.114:10158-10166.
Palese, P., D. Bucher, E.D. Kilbourne (Feb. 1973) “Applications of a Synthetic Neuraminidase Substrate”Applied Microbiology25(2):195-201.
Baumberger, Franz and Andrea Vasella (1986) “4-Methylumbelliferyl 5-Acetamido-3,4,5-trideoxy-α-D-manno2-nonulopyranosidionic Acid: Synthesis and Resistance to Bacterial Sialidases”Helvetica Chimica Acta69:1927-1935.
Zbiral, Erich, Erwin Schreimer, Mamikrao M. Salunkhe, Gerhard Schulz, Reinhard G. Kleineidam, Roland Schauer (1989) “Synthesis of the 4-Methyllumbeliferyl 2α-Glycosides of 7-Epi-, 8-Epi-, and 7,8-Bis(epi)-N-acetylneuraminic Acids, as well as of 7-Deoxy-, 8-Deoxy-, 9-Deoxy-, and 4,7-Dideoxy-N-acetylneuraminic Acids and Their Behaviour Towards Sialidase fromVibrio cholerae” Liebigs Ann. Chem. pp. 519-526.
Sigma catalog, 1993 edition, p. 33.
Derwont abstract; AN 90-14 3137 c19!; PN JP 2088594 (Mar. 28, 1990).
Briselden, Ann Marie, Bernard J. Moncia, Claire E. Stevens, Sharon L. Hillier (1992) “Sialidases (Neuraminidases) in Bacterial Vaginosis and Bacterial Vaginosis-Associated Microflora” J. Clinical Microbiology 30(3):663-668.
Bonten, Erik, Aarnoud van der Spoel, Maarten Fornerod, Gerard Grosveld, Alessandra d'Azzo (1996) “Characterization of human hysosomal neuraminidase defines the molecular basis of the metabolic storage disorder sialidosis” Genes & Development 10:3156-3169.
Cross, Geroge A.M., Garry B. Takle (1993) “The SurfaceTrans-sialidase Family OfTrypanosoma Cruzl” Ann. Rev. Microbiology 47:385-411.
Crennell, Susan, Elspeth Garman, Graeme Laver, Eric Vimr, Garry Taylor (1994) “Crystal structure ofVibrio choleraeneuraminidase reveals dual lectin-like domains in addition to the catalytic domain” Structure 2(6):535-44.
Crennell, Susan J., Elspeth F. Garman, W. Graeme Laver, Eric R. Vimr, Garry L. Taylor (1993) “Crystal structure of a bacterial sialidase (fromSalmonella typhimuriumLT2) shows the same fold as an influenza virus neuraminidase” Proc. Natl. Acad. Sci. USA 90:9852-9356.
Lentz, Michael R., Robert G. Webster, Gillian M. Air (1987) “Site-Directed Mutation of the Active Site of Influenza Neuraminidase and Implications for the Catalytic Mechanism” Biochemistry 26:(17):5351-5358.
Cabezas et al. (1980) “Nueraminidase from influenza virus A (H3N2)”Biochim. Et Biophys. Acta616:228-238.
Aamlid, Kai H., Grantham Lee, Brian V. Smith, Anthony C. Richardson, Robert G. Price (1990) “New colorimetric substrates for the assay of glycosidases” Carbohydrate Research 205:c5-c9.
Baggett, Neil and Brian J. Marsden (1982) “Reinvestigation Of The Synthesis Of 4-Methylcoumarin-7-YL 5-Acetamido-3, 5-Dideoxy-α-D-glycero-D-galacto-2-Nonulopyranosi-donic Acid, A Fluorogenic Substrate For Neuraminidase” Carbohydrate Research 110:11-18.
Eschenfelder, Volker and Reinhard Brossmer (1987) “Synthesis of p-nitrophenyl 5-acetamido-3, 5-dideoxy-α-D-Glycero-D-galacto-2-nonulopyranosidonic acid, a chromogenic substrate for sialldases” Carbohydr. Res. 162:294-297.
Eschenfelder, Volker and Reinhard Brossmir (1987) “5-Bromo-indol-3-yl 5-Acetamido-3, 5-dideoxy-α-D-glycero-D-galactononulopyranosidonic Acid, a Novel Chromogenic Substrate for the Staining of Sialidase Activity” Glycoconjugate J. 4:171-178.
Freudenberg, K., H. Resnik, H. Boesenberg, D. Rasenack (1952) “Das an der Verholzung Beteiligt Fermentsystem” Chem. Ber. 85:641-647.
Holmquist, L., R. Brossmer (1972) “Specificity of neuraminidase, synthesis and properties of the 2-aminoethyl α- and the 2-pyridyl α- and β-glycosides of N-acetyl-D-neuraminic acid” Hoppe-Seyler's Z. Physiol. Chem. 353:1346-1350.
Sinnott et al. (1993) “Leech sialidase L. cleaves the glycon-aglycon bond with the substrate in a normally disfavored conformation”J. Am. Chem. Soc. 115:3334-3335.
Horwitz, J.P., J. Chua, R.J. Curby, A.J. Tomson, M.A. Darooge, B.E. Fisher, J. Mauricio, I. Klundt (1964) “Substrates for Cytochemical Demonstration of Enzyme Activity. I. Some Substituted 3-Indolyl-β-D-glycopyranosides” J. Med. Chem. 7:574-575.
de Kiewiet, T.E., H. Stephen (1931) “2-Hydroxy-4-methoxy- and 4-Hydroxy-2-methoxy-benzaldehydes” J. Chem. Soc. 133:84-85.
Kuhn, Richard, Peter Lutz and Doanld L. MacDonald (1966) “Synthesa anomerer Sialinsäure-methylketoside” Chem. Ber. 99:611-617.
Ley, Arthur Newton, Raymond John Bowers, Saul Wolfe (1988) “Indoxyl-β-D-glucuronide, a novel chromogenic reagent for the specific detection and enumeration ofEscherichia coliin environmental samples” Can. J. Microbiol. 34:690-693.
Myers, R. W., R. T. Lee, Y. C. Lee, G. H. Thomas, L. W. Reynolds, Y. Uchida (1980) “The Synthesis of 4-Methylumbelliferyl α-Ketoside of N-Acetylneuraminic Acid and its Use in a Fluorometric Assay for Neuraminidase” Anal. Biochem. 101:166-174.
Ogura, Haruo and Kimio Furuhata (1986) “Syntheses Of 2-O-Glycosyl Derivatives of N-Acetyl-D-Neuraminic Acid” Carbohydrate Research 158:37-51.
Lehninger (1975) Biochemistry, 2ndedition, p. 594, Worth Publishers, Inc. New York.
Okamoto, Kaoru, and Toshio Gota (1990) “
Johnson Stephen C.
Luo Ming
Saeed Ashraf
IBBEX, Inc.
Khare Devesh
Saliwanchik Lloyd & Saliwanchik
Univ. of Alabama at Birmingham
Wilson James O.
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