Chemistry: natural resins or derivatives; peptides or proteins; – Proteins – i.e. – more than 100 amino acid residues – Blood proteins or globulins – e.g. – proteoglycans – platelet...
Patent
1994-01-28
1997-04-22
Raymond, Richard L.
Chemistry: natural resins or derivatives; peptides or proteins;
Proteins, i.e., more than 100 amino acid residues
Blood proteins or globulins, e.g., proteoglycans, platelet...
424450, 530345, 530350, 5303417, 530402, 558288, 558289, C07F 502
Patent
active
056230559
ABSTRACT:
The present invention relates to a novel class of bioconjugates derived from phenylboronic acid complexes, and the method of making and using such bioconjugate complexes. The complexes are in the form of the following general formulas. ##STR1## wherein group Q is selected from either O, S, NH, N-alkyl and N-aryl, wherein alkyl denotes a hydrocarbon moiety, wherein aryl is selected from either an aromatic ring, a substituted aromatic ring and fused aromatic rings, wherein group R is preferably selected from either O, NH, CH.sub.2, alkyl and aryl, wherein alkyl and aryl are as were previously defined,
REFERENCES:
patent: 2548257 (1951-07-01), Goldberg et al.
patent: 4269605 (1981-05-01), Dean et al.
patent: 4281181 (1981-07-01), Nagasawa et al.
patent: 4496722 (1985-01-01), Gallop et al.
patent: 4713346 (1987-12-01), Gallop et al.
patent: 4783487 (1988-11-01), Brune
patent: 4851443 (1989-07-01), Brune
patent: 4894229 (1990-01-01), Polson et al.
patent: 4910300 (1990-03-01), Urdea et al.
patent: 5002883 (1991-03-01), Bieniarz et al.
patent: 5045451 (1991-09-01), Uhr et al.
patent: 5093232 (1992-03-01), Urdea et al.
patent: 5183653 (1993-02-01), Linder et al.
patent: 5242842 (1993-09-01), Sundrehagen
Borrebaeck, Journal of Immunological Methods, vol. 123, pp. 157-165 (1989).
Wilcheck, M. & Bayer, E.A.; "Introduction to Avidin-Biotin Technology"; Methods in Enzymology; vol. 184; 1990 (USA).
Kessler et al.; "Non-radioactive Labeling and Detection of Nucleic Acids"; Biol. Chem. Hoppe-Seyler; vol. 371, pp. 917-927; 1990 (USA).
Singhal, R.P. & DeSilva, S.S.M.; "Boronate Affinity Chromatography"; Advances in Chromatography; vol. 31, pp. 293-335; 1992 (USA).
Mazzeo, J.R. & Krull, I.S.; "Immobilized Boronates for the Isolation and Separation of Bioanalytes"; Biochromatography; vol. 4, pp. 124-130; 1989.
Bergold, A. & Scouten, W.H.; "Borate Chromatography"; Solid Phase Biochemistry; Ch. 4, pp. 149-187; 1983 (USA).
Lorand, J.P. & Edwards, J.O.; "Polyol Complexes and Structure of the Benzeneboronate Ion"; J. Org. Chem.; vol. 24, p. 769; 1959 (USA).
Bowie, R.A. & Musgrave, O.C.; "Organoboron Compounds. Part V.* The Hydrolysis of Cyclic Phenylboronates"; J. Amer. Chem. Soc.; pp. 3945-3949; 1963 (USA).
Sienkiewicz, P.A. & Roberts, D.C.; "pH Dependence of Boronic Acid-Diol Affinity in Aqueous Solution"; J. Inorg. Nucl. Chem.; vol. 42, pp. 1559-1571; 1980 (USA).
Tanner, D.W. & Bruice, T.C.; "Boric Acid Esters" J. Amer. Chem. Soc.; vol. 89, pp. 6954-6971; 1967 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate von Salicylaldoxim und Derivaten"; Monatshefte Fur Chemie; vol. 114, pp. 465-484; 1983 (FRG).
Imagawa et al.; "Characteristics and Evaluation of Antibody-Horseradish Perioxidase Conjugates, etc."; J. Applied Biochemistry; vol. 4, pp. 41-57; 1982 (USA).
Kessler, C.; Advances in Mutagenesis Research (Obe, G. ed.); pp. 105-152; Springer-Verlag, Berlin/Heidelberg; 1990 (USA).
Brinkley, M.; "A Brief Survey of Methods for Preparing Protein Conjugates with Dyes, Haptens, and Cross Linking Reagents"; Bioconjugate Chem.; vol. 3; pp. 2-13; 1992 (USA).
Linder et al.; "Technetium Labeling of Monoclonal Antibodies with Functionalized BATOs 1. TcCl(DMG).sub.3 PITC"; Bioconjugate Chem.; vol. 2, pp. 160-170; 1991 (USA).
Linder et al.; "Technetium Labeling of Monoclonal Antibodies with Functionalized BATOs 2. TcCl(DMG).sub.3 CPITC Labeling of B72.3, etc." Bioconjugate Chem.; vol. 2, pp. 407-415; 1991(USA).
Burnett et al.; "Synthesis of a Fluorscent Boronic Acid Which Reversibly Binds to Cell Walls, etc."; Biochem. Biophys. Research Commun.; vol. 96, pp. 157-162; 1980 (USA).
Steinberg, G.M. & Swidler, R.; "The Benzohydroxamate Anion"; J. Org. Chem. Vol.; vol. 30, pp. 2362-2365; 1965 (USA).
Bauer, L. & Exner, O.; "The Chemistry of Hydroxamic Acids and N-Hydroxyimides"; Angew. Chem. Internat. Edit.; vol. 13, pp. 376-384; 1974 (USA).
Cai, S.X. & Kean, J.; ".smallcircle.-Acetomidophenylboronate Esters Stabilized Toward Hydrolysis by an Intramolecular O-B Interation, etc."; Bioconjugate Chem.; vol. 2, pp. 317-322; 1991 (USA).
Ramalingam, K. & Nowotnik, D.; "Syntheses of Some Isothiocyanatophenylboronic Acids"; Org. Prep. Proc. Int.; vol. 23, 729-734; 1991 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate Von Salicyladehydnitronen"; Journal of Organometallic Chem.; vol. 243, pp. 373-385; 1983 (USA).
Roberts et al.; "Pluripotential Amino Acids"; Tetrahedron Letters; vol. 21, pp. 3435-3438; 1980 (USA).
Kemp, D.S. & Roberts, D.; "New Protective Groups for Peptide Synthesis--II The DOBZ Group, etc."; Tetrahedron Letters; vol. 52, pp. 4629-4632; 1975 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate von N-substituierten Hydroxamsauren"; Chem. Ber.; vol. 116, pp. 2616-2629; 1983 (FRG).
Mikesova, M. & Bartusek, M.; "Reaction of Boric Acid with Salicylic and Chromotropic Acids and with Their Derivatives"; Chem. Zvesti; vol. 32(4), pp. 472-477; 1978.
Feeney, R.E., "Chemical Modification of Proteins: Comments and Perspectives"; Int. J. Peptide Protein Res.; vol. 29, pp. 145-161 (USA), 1987.
Means, G.E. & Feeney, R.E.; "Chemical Modifications of Proteins: History and Applications"; Bioconjugate Chem.; vol. 1, pp. 2-12 (USA), 1990.
O'Shannessy, D.J. & Quarles, R.H.; "Labeling of the Oligosaccharide Moieties of Immunoglobulins"; J. Immunological Methods; vol. 99, pp. 153-161 (1987)(USA).
van't Reit, B., Wampler, G.L., & Elford, H.L.; "Synthesis of Hydroxy-and Amino-Substituted Benzohydroxamic Acids, etc."; J. Medicinal Chem.; vol. 22, No. 5, 589-92, 1979 (USA).
Soundararajan, et al.; "Boronic Acids for Affinity Chromatography: Spectral Methods for Determination, etc."; Analytical Biochem.; vol. 178, pp. 125-134, 1989 (USA).
Goodchild, J.; "Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and Properties"; Bioconjugate Chem.; vol. 1, No. 3, pp. 165-193, 1990 (USA).
Kessler, C.; Nonradioactive Labeling and Detection of Biomolecules; Ch. 1-3, 1992 (USA).
Meares, C.F., "Editorial; Introduction to Bioconjugate Chemistry"; Bioconjugate Chem.; vol. 1, No. 1, 1990 (USA).
Waggoner, A.S.; "Fluorescent Probes for Cytometry"; Flow Cytometry and Sorting; 2nd ed; pp. 209-225; 1990 (USA).
Chen, et al.; "Structure-Activity Relationships in a Series of 5-[(2,5-Dihydroxybenzyl) amino]salicylate, etc."; Chemical Abstracts; vol. 120; 322877v; 1994 (USA).
Hirano, et al.; "Silver halide color photographic material"; Chemical Abstracts; vol. 116; 140012u; 1992 (USA).
Kawasaki, et al.; "Silver halide photographic material with improved storage stability"; Chemical Abstracts; vol. 109; 160505r; 1988 (USA).
Priewe, H., et al.; ".smallcircle.-Hydroxybenzohydroxamic Acids"; Chemical Abstracts; vol. 52; 10184; 1958 (USA).
Prolinx, Inc.
Raymond Richard L.
LandOfFree
Phenylboronic acid complexes derived from aminosalicylic acid fo does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Phenylboronic acid complexes derived from aminosalicylic acid fo, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenylboronic acid complexes derived from aminosalicylic acid fo will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-342614