Organic compounds -- part of the class 532-570 series – Organic compounds – Boron acids or salts thereof
Patent
1997-02-25
1999-12-28
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Boron acids or salts thereof
530345, 530350, 5303911, 5303917, 536 171, C07F 502, C07F 504
Patent
active
060084065
ABSTRACT:
The present invention relates to novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.3, wherein group Y is selected from either O, S and NH, and wherein group Z comprises a spacer which either separates the boronic acid complexing moiety from group R, as in General Formula I, or seperates two boronic acid complexing moieties, as in General Formula II. Group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the phenylboronic acid complexing reagent with a bioactive species.
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.
Wilcheck, M. & Bayer, E.A.; "Introduction to Avidin-Biotin Technology"; Methods in Enzymology; vol. 187; 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 Chromotography"; Advances in Chromatography; vol. 31, pp. 293-335; 1992 (USA).
Mazzeo, J.R. & Krull, I.S.; "Immobilized Boronates for the Isolation and Seperation 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.; "Technitium Labeling of Monoclonal Antibodies with Functionalized BATOs 1. TcCI(DMG).sub.3 PITC"; Bioconjugate Chem.; vol. 2, pp. 160-170; 1991 (USA).
Linder et al.; "Technitium Labeling of Monoclonal Antibodies with Functionalized BATOs 2. TcCI(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.; "Synthesis of Some Isothiocyanatophenylboronic Acids"; Org. Prep. Proc. Int.; vol. 23, 729-34; 1991 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate Von Salicyladehydnitronen"; Journal of Organometallic Chem.; vol. 24, pp. 373-385; 1983 (USA).
Ripan et al.; "Etude Du Systeme Acide Borique-Salcylaldoxime en Solutions Aqueuses"; Revue Roumaine de Chimie; vol. 10, pp. 965-971; 1965 (FRA).
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).
Kleigel, 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, 589-592, 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).
Borrebaeck, C.; "Strategy for the production of human monoclonal antibodies using in vitro activated B cells"; J. Immun. Methods; vol. 123; 157-165; 1989 (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 photgraphic material"; Chemical Abstracts; vol. 116; 140012u; 1992 (USA).
Kawasaki, et al.; "Silver halide phographic material with improved storage stablity"; 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.
LandOfFree
Phenylboronic acid complexing reagents derived from aminosalicyl 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 complexing reagents derived from aminosalicyl, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenylboronic acid complexing reagents derived from aminosalicyl will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2383484