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
1997-01-14
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, 5303917, 530402, 558288, 558289, C07F 502
Patent
active
055941117
ABSTRACT:
The present invention relates to a novel class of phenylboronic acid bioconjugate complexes derived from aminosalicylic acid, and the method of making and using such bioconjugate complexes. The bioconjugate complexes are in the form of the following general formulas; ##STR1## wherein group X is selected from the group consisting of O, NH, N-alkyl, NC.sub.6 H.sub.5, N-aryl, NCH.sub.2 -aryl, NCH.sub.2 CH.sub.2 OH, NCOCH.sub.2 CH.sub.2 OH, NOH, NO-alkyl and NOCH.sub.2 -aryl, wherein alkyl denotes a hydrocarbon moiety of from 1 to 4 carbons in length and which may be linear or branched, wherein aryl is selected from the group consisting of an aromatic ring, a substituted aromatic ring and a fused aromatic ring,
wherein group Y is selected from the group consisting of O, S, NH, N-alkyl, N-aryl and NCH.sub.2 -aryl,
wherein groups Z and Z* comprise a spacer selected from an alkyl and a polyethyleneglycol chain, of from 1 to 16 carbon equivalents in length, wherein the chain may contain intermediate amide and disulfide bonds, and
and wherein groups BAS and BAS* are bioactive species.
REFERENCES:
patent: 2548257 (1951-03-01), 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 Slicylaldoxim 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.; "o-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. Zvest; 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, 589-592, 1979 (USA).
Soundararajan, et al.; "Boronic Acids for Affinity Chromatography: Spectral Methods for Determination, etc."; Analytical Biochem.; vol. 178, pp. 124-134, 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.; "o-Hydroxybenzohydroxamic Acids"; Chemical Abstracts; vol. 52; 10184; 1958 (USA).
Prolinx, Inc.
Raymond Richard L.
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