Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-10-21
1999-09-21
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540205, 435 18, 435805, C07D50114, C12Q 134
Patent
active
059556048
ABSTRACT:
Substrates for .beta.-lactamase of the general formula I ##STR1## in which one of X and Y is a fluorescent donor moiety and the other is a quencher (which may or may not re-emit); R' is selected from the group consisting of H, lower (i.e., alkyl of 1 to about 5 carbon atoms) and (CH.sub.2).sub.n OH, in which n is 0 or an integer from 1 to 5; R" is selected from the group consisting of H, physiologically acceptable metal and ammonium cations, --CHR.sup.2 OCO(CH.sub.2).sub.n CH.sub.3, --CHR.sup.2 OCOC(CH.sub.3).sub.3, acylthiomethyl, acyloxy-alpha-benzyl, delta-butyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, beta-morpholinoethyl, dialkylaminoethyl, acyloxyalkyl, dialkylaminocarbonyloxymethyl and aliphatic, in which R.sup.2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO.sub.2 and CH.sub.2 ; and Z' and Z" are linkers for the fluorescent donor and quencher moieties. Methods of assaying .beta.-lactamase activity and monitoring expression in systems using .beta.-lactamase as a reporter gene also are disclosed.
REFERENCES:
patent: 4234683 (1980-11-01), McMillan
patent: 4383032 (1983-05-01), Stahl et al.
patent: 4448880 (1984-05-01), Schindlen et al.
patent: 4740459 (1988-04-01), Chen et al.
patent: 4760018 (1988-07-01), Charm
patent: 4764462 (1988-08-01), Bredehorst et al.
patent: 4978613 (1990-12-01), Bienlarz et al.
patent: 5162524 (1992-11-01), Farina
patent: 5264346 (1993-11-01), Cen
patent: 5338843 (1994-08-01), Quante et al.
patent: 5501979 (1996-03-01), Geller
patent: 5514561 (1996-05-01), Quante et al.
patent: 5583217 (1996-12-01), Quante et al.
patent: 5593866 (1997-01-01), Hancock
patent: 5639596 (1997-06-01), Born Kamm
patent: 5741657 (1998-04-01), Tsien et al.
Broach and Thorner, Nature, 384:14-16 (Nov. 1996).
Cartwright et al., Yeast 8:261-272 (1992).
Darnell, Molecular Cell Biology, Scientific American Books, Inc. N.Y. (1986) pp. 570-573.
Davis et al., Microbiology, Third Edition, Harper & Row, PA (1980).
Zlokarnik et al., Science, 279:84-88 (1998).
L.A. Castelli et al., "High-level secretion of correctly processed .beta.-lactamase from Saccharomyces cerevisiae using a high-copy-number secretion vector", Gene 142 (1994) pp. 113-117.
M. Wiedmann et al., "Xenopus oocytes can secrete bacterial .beta.-lactamase", Nature, vol. 309, Jun. 14, 1984, pp. 637-639.
Charles P. Cartwright et al., "Use of .beta.-Lactamase as a Secreted Reporter of Promoter Function in Yeast", Yeast, vol. 10:497-508 (1994).
Kay Simon et al., "Translocation of Globin Fusion Proteins across the Endoplasmic Reticulum Membrane in Xenopus laevis Oocytes", The Journal of Cell Biology, vol. 104, May 1987, pp. 1165-1172.
Sui-Lam Wong, "Development of an inducible and enhancible expression and secretion system in Bacillus subtilis", Gene, 83 (1989) pp. 215-223.
Hans R. Waterham et al., "The Hansenula polymorpha PER1 Gene Is Essential for Peroxisome Biogenesis and Encodes a Peroxisomal Matrix Protein with Both Carboxy- and Amino-terminal Targeting Signals", The Journal of Cell Biology, vol. 127, No. 3, Nov. 1994, pp. 737-749.
Pablo D. Garcia et al., "Wild Type Mutant Signal Peptides of Escherichia coli Outer Membrane Lipoprotein Interact with Equal Efficiency with Mammalian Recognition Particle", The Journal of Biological Chemistry, vol. 262, No. 20, Issue of Jul. 15, 1987, pp. 9463-9468.
Gorman, C.M. et al., "Recombinant Genomes which Express Chloramphenicol Acetyltransferase in Mammalian Cells", Mol. Cell. Bio. 2:1044-1051 (1982).
Alam J. And Cook J.L., "Reporter Genes: Application to the Study of Mammalian Gene Transcription", Analytical Biochemistry, 188, 245-254 (1990).
Rosenthal, N., Identification of Regulatory Elements of Cloned Genes with Functional Assays, Methods Enzymol., 152:704-720 (1987).
Shiau, A. et al., "Improved cat gene cassette for promoter analysis and genetic constructions", Gene 67 (1988) 295-299.
Stryer, I., "Introduction to Enzymes" Biochemistry, 1981, pp. 103-134.
Chang, Y.H et al., "Altering enzymatic activity: Recruitment of carboxypeptidase activity into an RTEM .beta.-lactamase/pencillin-binding protein 5 chimera", Proc. Nat. Acad. Sci., USA vol. 87, pp. 2823-2827, Apr., 1990.
Tsien et al., "Fluorophores for Confocal Microscopy: Photophysics and Photochemistry", Handbook of Biological Confocal Microscopy, edited by James B. Pawley, Plenum Publishing Corp., 1990, pp. 169-178.
Bundgaard, "Design of prodrugs: Bioreversible derivatives for various functional groups and chemical entities", Elsevier Science Publishers (1985).
Bundgaard H., "Design of Bioreversible Drug Derivatives and the Utility of the Double Prodrug Concept", New York Pergamon Press (1987).
Ferres H., "Pro-drugs of .beta.-lactam antibiotics", Chem. Ind., Jun., 1980, pp. 435-440.
Christensen, M. et al., ".beta.-Lactamases as fully efficient enzymes", Biochem. J. (1990) 266, 853-861.
O'Callaghan. C.H. et al., "Effects of .beta.-Lactamase from Gram-negative Organisms on Cephalosporins and Penicillins", Antimicrobial Agents and Chemotherapy (1968), pp. 57-63.
Stratton, C.W., "Activity of .beta.-lactamases against .beta.-lactams", Journal of Antimicrobial Chemotherapy, (1988) 22, Supp. A 23-35.
Waley, S.G., ".beta.-Lactamases a major cause of antibiotic resistance", Sci. Prog. Oxf. (1988) 72, 579-597.
Richmond, M.H. et al., "The .beta.-Lactamases of Gram-Negative Bacteria Including Pseudomonads*", Ann. N.Y. Acad. Sci., 182: 243-257 (1971).
Ambler R.P., "The structure of .beta.-lactamases", Phil. Trans. R. Soc. Lond. B 289, 321-331 (1980).
Castagnoli L. et al., "The phasmid as a tool for phasmid genetics", Genet. Res. 40: 217-231 (1982).
Pratt R.F. et al., ".beta.-Lactamase-catalyzed hydrolysis of acyclic depsipeptides and acyl transfer to specific amino acid acceptors", Proc. Natl. Acad. Sci. USA vol. 81, pp. 1302-1306, Mar. 1984.
Murphy B.P. et al., "N-(Phenylacetyl)glycyl-D-aziridine-2-carboxylate, an Ayclic Amide Substrate of .beta.-Lactamases: Importance of the Shape of the Substrate in .beta.-Lactamase Evolution", Biochemistry, 1991, 30, 3640-3649.
Bush K., "Methodology for the Study of .beta.-Lactamases", Antimicrobial Agents and Chemotherapy, Jul. 1986, pp. 6-10 (1986).
Jansen, A.B.A. et al., "Some Novel Penicillin Derivatives," J. Chem. Soc., 2127-2132 (1965).
Daehne W.V. et al., "Acyloxymethyl Esters of Ampicillin", J. Med. Chem. 13:607-612 (1970).
Jones, R.N. et al., "In Vitro Evaluation of Pyridine-2-Azo-p-Dimethylaniline Cephalosporin, a New Diagnostic Chromogenic Reagent, and Comparison with Nitrocefin, Cephacetrile, and Other Beta-Lactam Compounds", J. Clin. Microbiol., 15:677-683 (1982).
Jones R.N., "In Vitro Evaluation of CENTA, a New Beta-Lactamase-Susceptible Chromogenic Cephalosporin Reagent", J. Clin. Microbiol., 15:954-958 (1982).
O'Callaghan C.H. et al., "Novel Method for Detection of .beta.-Lactamases by Using a Chromogenic Cephalosporin Substrate", Antimicrob. Agents Chemother., 1:283-288 (1972).
Richmond M.H., "The .beta.-Lactamases of Gram-Negative Bacteria and their Possible Physiological Role", Adv. Microb. Physiol., 9:31-88 (1973).
Kadonaga J.T. et al., "The Role of the .beta.-Lactamase Signal Sequence in the Secretion of Proteins by Escherichia coli*", The Journal of Biological Chemistry, vol. 259, No. 4, Feb. 25, 1984, pp. 2149-2154.
Sutcliffe J.G., "Nucleotide sequence of the ampicillin resistance gene of Escherichia coli plasmid pBR322", Proc. Natl. Acad. Sci., vol. 75, No. 8, pp. 3737-3741, Aug. 1978.
Forster V.T., "Zwischenmolekulare Energiewanderung and Fluoreszenz", Ann. Physik 2:55-75.
Lakowicz J.R., Principles of Fluorescence Spectroscopy, New York:Plenum Press (1983) Herman B., Resonnance energy transfer microscopy, in:Fluorescence Microscopy of Living Cells in Culture, Part B, Methods in Cell. Biology, vol. 30, ed.
Taylor D.I. et al., San Diego: Academic Press (1989) pp. 219-243.
Turro N.J., "Modern Molecular Photochemistry", Menlo Part:Benjamin/Cummings Publishing Co., Inc., 1978, pp. 296-361.
Berlman I.B., "Energy transfer parameters of aromatic compounds", Acadamic Press New York and Lon
Tsien Roger Y.
Zlokarnik Gregor
Raymond Richard L.
Sripada Pavanaram K
The Regents of the University of California
LandOfFree
Substrates for .beta.-lactamase and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substrates for .beta.-lactamase and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substrates for .beta.-lactamase and uses thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-81692