Sulfur Containing Reactant Patents (Class 530/408)
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Patent number: 5239062Abstract: An activated affinity ligand is described comprising: a ligand having (a) a region with affinity for binding sites of a lectin; and (b) a reactive group capable of covalently linking the ligand to the lectin to thereby block one or more of the binding sites of the lectin. A blocked lectin is described comprising one or more affinity ligands covalently linked by means of a reactive group present on each of the ligands to a lectin such that one or more binding sites of the lectin is blocked. A cell-binding agent-blocked lectin conjugate is described comprising the above-described blocked lectin and a cell-binding agent covalently linked to: (a) one of the covalently linked affinity ligands; or (b) the lectin. A method of preparing a blocked lectin is described. A method of preparing the cell-binding agent-blocked lectin conjugate is described. An affinity support capable of binding to a lectin to form a blocked lectin is described comprising an activated affinity ligand covalently linked to a solid support.Type: GrantFiled: July 31, 1990Date of Patent: August 24, 1993Assignee: Dana-Farber Cancer Institute, Inc.Inventors: Walter A. Blattler, John M. Lambert, Victor S. Goldmacher, Ravi V. J. Chari, Charles F. Scott, Jr., Linda J. Kostuba, Simon E. Moroney, Albert R. Collinson
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Patent number: 5227309Abstract: A method for the C-terminal sequencing of a peptide in which an alkyl or aryl tin isothiocyanate coupling reagent is used to form a thiohydantoin derivative. Free halogen producing activating agents, such as 2-halo-1-methyl pyridinium salts, may be used as an activating agent for the coupling reagent.Type: GrantFiled: October 18, 1991Date of Patent: July 13, 1993Assignee: City of HopeInventors: Jerome Bailey, John E. Shively, Narmada R. Shenoy
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Patent number: 5223435Abstract: Sequential degradation of peptides for sequencing purposes by successive cleavage of amino acids from one end of the peptide chain is performed in an adsorption column with flows of the degradation reagents and wash liquids passing through the column in both directions. Migration of the peptide in one direction is thereby compensated by a subsequent migration in the other, and loss of peptide from the column over repeated cleavages is avoided. In preferred embodiments, the column contains two serially arranged adsorbent zones with differing adsorption characteristics, and the directions of flow of the various system components through the column are selected with a view toward a difference in peptide partitioning between the stationary and mobile phases in one zone vs. the other. The result is that any migration of the peptide occurring at any stage of a given cycle of the procedure occurs at a greater rate toward the zone interface than away from it.Type: GrantFiled: October 25, 1991Date of Patent: June 29, 1993Assignee: Genetech, Inc.Inventor: William J. Kohr
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Patent number: 5219895Abstract: Collagen-based compositions as adhesives and sealants for medical use and preparation thereof are described. Prior to polymerization, soluble or partially fibrillar collagen monomers in solution are chemically modified with an acylating agent, sulfonating agent or a combination of the foregoing. The collagen compositions prepared accordingly can be used as medical adhesives for bonding soft tissues or be made in to a sealant film for a variety of medical uses such as wound closures and tendon wraps for preventing adhesion formation following surgery.Type: GrantFiled: January 29, 1991Date of Patent: June 15, 1993Assignee: Autogenesis Technologies, Inc.Inventors: Charles D. Kelman, Dale P. DeVore
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Patent number: 5204448Abstract: A new series of bifunctional chelating agents useful for attaching metal ions to proteins, polypeptides and other polymers and methods for their preparation are described. These reagents are unique in their ability to bind a variety of metal ions and to yield a high metal ion concentration per protein molecule. Using these methods polymeric analogs of these bifunctional chelating agents called Starburst ligands can also be obtained. Protein metal chelates thus obtained will have useful radiophysical, chemical, fluorescent, photochemical and magnetic properties suitable for biomedical applications.Type: GrantFiled: May 26, 1989Date of Patent: April 20, 1993Assignee: Akzo N.V.Inventor: Ramaswamy Subramanian
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Patent number: 5204098Abstract: Vi capsular polysaccharides conjugated to toxin-dependent proteins can be used to enhance antibody response and to convert T-dependent properties to the Vi capsular polysaccharide. A heterobifunctional crosslinking agent can be used to bind thiol derivatives of the Vi capsular polysaccharides to the proteins, such as diphtheria, tetanus toxoids, cholera toxin and Haemophilus influenzae.Type: GrantFiled: February 16, 1988Date of Patent: April 20, 1993Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Shousun C. Szu, Rachel Schneerson, John B. Robbins
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Patent number: 5202423Abstract: The invention pertains to terpyridine compounds having structure (I). These compounds form fluorescent lanthanide chelates with the appropriate metal ions. The fluorescent metal chelates are useful as probes in time-resolved fluorescence spectroscopy.Type: GrantFiled: April 19, 1991Date of Patent: April 13, 1993Assignee: Wallac OyInventors: Jouko Kankare, Harri Takalo, Elina Hanninen, Matti Helenius, Veli-Matti Mukkala
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Patent number: 5187259Abstract: A soluble, chain extended gelatin having a high molecular weight and significantly higher viscosity at equivalent gelatin concentration compared to standard gelatin and significantly faster setting time is produced by preparing an aqueous gelatin composition containing from about 6% to about 18% dry weight of gelatin and from about 0.25 to about 5 millimoles of a bis-(vinyl sulfonyl) compound per 100 grams of gelatin, heating the composition at a temperature of from about 40 to about 60.degree.C. and at a pH of from about 4.5 to about 7 for from about one to about eight hours.Type: GrantFiled: November 14, 1990Date of Patent: February 16, 1993Assignee: Eastman Kodak CompanyInventors: Melvin D. Sterman, James L. Bello
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Patent number: 5185433Abstract: The present invention provides cross-linked protein compositions consisting of two or more units of a target-specific protein joined by binding sulfhydryl groups on the target-specific protein units to a sulfhydryl-selective cross-linking agent and a method of making the compositions. These cross-linked protein compositions combine an increase in binding affinity due to the presence of multiple identical binding sites and stability to reduction conditions.Type: GrantFiled: April 9, 1990Date of Patent: February 9, 1993Assignee: Centocor, Inc.Inventors: Richard T. Dean, John Lister-James, Raymond H. Boutin
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Patent number: 5180815Abstract: Modified proteins for carrying hapten are provided. These carriers are prepared by blocking the amino groups of the original protein and then introducing amino groups into the carboxyl groups of the original protein. The blocking groups may be eliminated at the later stage to regenerate the amino groups of the original protein. The modified protein or polypeptide carrier have the three-dimensional structures different from the original proteins so that they are used in immunoassay while carrying low molecular weight haptens without the fear of forming antibodies for the original proteins. The modified protein carrier may also be used in the passive agglutination immunoassay without the need of absorbing the anti-hapten antibodies by the hapten-carrying carriers.Type: GrantFiled: May 5, 1992Date of Patent: January 19, 1993Assignee: Fuji Photo Film Co., Ltd.Inventor: Nobuhito Masuda
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Patent number: 5177192Abstract: Methods for rapidly labeling sulfhydryl-containing antibodies or fragments with technetium or rhenium radioisotopes are disclosed. The method generally involves combining an aqueous mixture of the radiometal in an oxidized form, a reducing agent and a water-soluble polyhydroxycarbonylic acid ligand to form a stable complex of the radiometal in its reduced state and contacting the mixture with the sulfhydryl-containing antibody or fragment to produce a radiometal-labeled antibody or fragment.Type: GrantFiled: October 19, 1990Date of Patent: January 5, 1993Assignee: Centocor, IncorporatedInventors: Koon Y. Pak, Richard T. Dean, Jeffrey A. Mattis
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Patent number: 5175257Abstract: Chelating compounds of specified N.sub.2 S.sub.2 N.sub.3 S derived structure are useful for radiolabeling targeting molecules such as antibodies. Cleavable ester orthioester linkers connect the radionuclide metal chelates to the antibodies. The radiolabeled antibodies have improved biodistribution properties, including reduced localization within the intestines and kidneys.Type: GrantFiled: January 14, 1991Date of Patent: December 29, 1992Assignee: NeoRx CorporationInventors: Sudhakar Kasina, Ananthachari Srinivasan, John M. Reno, Linda M. Gustavson, Jeffrey N. Fitzner, David S. Jones
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Patent number: 5175256Abstract: Novel labeling reagents are useful for radiolabeling proteins such as antibodies with radionuclide metals such as .sup.99m Tc, .sup.186 Re, and .sup.188 Re. The reagents are of the following formula: ##STR1## wherein: each X is independently chosen from O, S, NH, or NR.sub.2, wherein R.sub.2 is a protecting group or an electron withdrawing group;R.sub.1 represents a protecting group, wherein each R.sub.1 is a separate protecting group or the two R.sub.1 symbols are taken together to represent a single protecting group; andeach T is independently chosen from hydrogen, lower alkyl groups of from 1 to about 6 carbon atoms, electron withdrawing groups, and lower alkyl groups of from 1 to about 6 carbon atoms substituted with electron withdrawing group(s).Type: GrantFiled: September 28, 1990Date of Patent: December 29, 1992Assignee: NeoRx CorporationInventors: Sudhakar Kasina, Ananthachari Srinivasan, James Sanderson, Alan R. Fritzberg
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Patent number: 5171846Abstract: A method for preparing a phycobiliprotein-Texas Red conjugate which overcomes the energy transfer/fluorescent quenching dilemma is disclosed. A phycobiliprotein, such as phycoerythrin, is conjugated with dye, such as Texas Red, in the presence of a selective salt which causes a hydrophobic intramolecular rearrangement of the phycobiliprotein thereby exposing more hydrophobic sites for binding to Texas Red. The conjugate is useful in multiple color fluorescence assays without requiring the use of multiple exciting sources.Type: GrantFiled: May 21, 1990Date of Patent: December 15, 1992Assignee: Coulter CorporationInventor: Ravinder K. Gupta
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Patent number: 5169933Abstract: Covalently-linked complexes (CLCs) for targeting a defined population of cells, comprising a targeting protein; a cytotoxic agent; and an enhancing moiety, wherein the enhancing moiety is capable of promoting CLC-target cell interaction are disclosed. Methods for using the claimed CLCs to obtain enhanced in vivo cytotoxicity and enhanced in vivo imaging are also described.Type: GrantFiled: August 7, 1989Date of Patent: December 8, 1992Assignee: NeoRx CorporationInventors: David C. Anderson, A. Charles Morgan, Jr., Paul G. Abrams, Alan R. Fritzberg, Everett J. Nichols
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Patent number: 5164488Abstract: The invention relates to compounds of formula: ##STR1## in which m, n, p and q are equal to 0 or 1, p being different from q and the sum m+n+p+q being equal to 2, A denotes a nonionic chain arrangement chosen from the groups:C.sub.2 H.sub.4 O.sub.r and/orC.sub.3 H.sub.5 (OH)O.sub.s,in which r denotes a number which can assume all integral values between 0 and 5 or a statistical average value between 0 and 20,s denotes a number which can assume all integral values between 0 and 5 or a statistical average value between 0 and 10,u is equal to 0 or 1, with the restriction that when u=0, s and r are also zero,R denotes(i) a linear or branched hydrocarbon radical which has 1 to 32 carbon atoms and can contain one or more oxygen atoms in the chain or bear one or more OH groups or(ii) a (C.sub.8 -C.sub.18 alkyl)phenyl radical.These compounds can be used for preparing stable chemical compounds, for conveying active substances or for forming vesicles.Type: GrantFiled: February 13, 1991Date of Patent: November 17, 1992Assignee: L'OrealInventors: Guy Vanlerberghe, Alexandre Zysman, Henri Sebag
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Patent number: 5162502Abstract: The present invention relates to a novel glycoprotein, extracted from the seeds of Trichosanthes kirilowii, called: trichokirin, as well as to its modified derivatives containing a free or blocked SH group. It relates to a process for its preparation, to its use and to pharmaceutical compositions in which it is present.Type: GrantFiled: June 13, 1991Date of Patent: November 10, 1992Assignee: SanofiInventors: Luigi Barbieri, Pierre Casellas, Fiorenzo Stirpe
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Patent number: 5162218Abstract: Polypeptide compositions are provided having a binding site specific for a particular target ligand and further having an active functionality proximate the binding site. The active functionality may be a reporter molecule, in which case the polypeptide compositions are useful in performing assays for the target ligand. Alternatively, the active functionality may be a chemotherapeutic agent, in which case the polypeptide compositions are useful for therapeutic treatment of various diseased states. A novel method for preparing such polypeptides having active functionalities proximate their binding site comprises combining the polypeptide specific for the target ligand with an affinity label including ligand having a reactive group attached thereto. The reactive group is then covalently attached to an amino acid side chain proximate the binding site and cleaved from the substrate. The substrate is eluted, leaving a moiety of the reactive group covalently attached to the polypeptide.Type: GrantFiled: June 10, 1991Date of Patent: November 10, 1992Assignee: The Regents of the University of CaliforniaInventor: Peter Schultz
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Patent number: 5162505Abstract: Protein conjugates comprising a protein covalently linked to at least one positively charged agent, so that the protein conjugate has an overall net positive charge in aqueous conditions at physiological pH are disclosed. The positively charged agents comprise polymers of three or more subunits selected from the group consisting of amino acids containing positively charged side chains and alkylamines. These protein conjugates have decreased blood clearance rates compared to conjugates which do not have the positively charged agents. The protein conjugates may further comprise diagnostic or therapeutic radionuclides bound to the protein or the positively charged agent through bifunctional coupling agents.Type: GrantFiled: September 19, 1989Date of Patent: November 10, 1992Assignee: CentocorInventors: Richard T. Dean, Raymond H. Boutin, John Lister-James
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Patent number: 5155166Abstract: Useful materials for diagnostic tests, affinity chromatography, enzymatic reactions and immunoassays are prepared by covalently attaching reactive compounds containing reactive amino or sulfhydryl groups to polymeric particles having pendant carboxyl groups on the outer surfaces. Such reactive compounds include biologically reactive species, including enzymes, polypeptides and proteins. This attachment is carried out using specific carbamoylonium compounds, namely certain 1-(1-pyrrolidinylcarbonyl)pyridinium salts. These compounds react with the carboxyl groups on the particles to form intermediate reactive groups which then react with the amino or sulfhydryl groups to form a covalent linkage between particle and reactive compound. A kit comprises polymeric particles having carboxyl groups on the outer surfaces, and a 1-(1-pyrrolidinylcarbonyl)pyridinium salt.Type: GrantFiled: June 18, 1990Date of Patent: October 13, 1992Assignee: Eastman Kodak CompanyInventors: Susan J. Danielson, Donald P. Specht
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Patent number: 5155212Abstract: The present invention is directed to a fluorescence polarization assay for phencyclidine and phencyclidine derivatives, to the various components needed for preparting and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for making them, and a reagent kit containing them. The tracers and the immunogens are made from substituted phencyclidine compounds. A fluorescein moiety is included in the tracer, while a poly(amino acid) forms a part of the immunogen. The assay is conducted by measuring the degree of polarization retention of plane polarized light that has been passed through a sample containing antiserum and tracer.Type: GrantFiled: May 29, 1990Date of Patent: October 13, 1992Assignee: Abbott LaboratoriesInventors: Robert E. Dubler, Mary P. Frintner, Jonathan Grote, Gregg A. Hadley, David J. Hawksworth, Hal D. Hopkins, Daniel S. Nam, Frank S. Ungemach, Larry K. Wray
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Patent number: 5155210Abstract: The invention provides for antinomycin D derivatives and methods of producing antinomycin D derivatives. Such derivatives include isocyanate, thioisocyanate, carboxylic acid, bromide, aldehyde and sulfonic acid derivatives. The invention also provides for actinomycin D derivatives conjugated to target cell binding proteins. Methods are provided to make such conjugates through attachment of the derivatized moiety to a reactive group on a target cell binding protein or on a spacer. The conjugates can be administered to an animal and produce localized cytotoxic effects on target cells.Type: GrantFiled: September 11, 1990Date of Patent: October 13, 1992Assignee: Brunswick CorporationInventor: Wolfgang A. Wrasidlo
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Patent number: 5153312Abstract: The present invention relates to an improved method for producing oligosaccharide conjugate vaccines. In an additional aspect of the invention, oligosaccharide vaccines are produced which elicit a monospecific and homogeneous immune response to capsular polysaccharide. A specific embodiment of the invention provides for vaccines which induce immunity to prevalent serotypes of Streptococcus pneumoniae.Type: GrantFiled: September 28, 1990Date of Patent: October 6, 1992Assignee: American Cyanamid CompanyInventor: Massimo Porro
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Patent number: 5149528Abstract: Purified cytotoxic proteins for use within therapeutic compositions are disclosed. The proteins inhibit protein synthesis in vitro, exhibit abortifacient activity in mice, and contain proline residues with equivalent positions at residue 43 and residue 46 in ricin A-chain. A method for preparing such a cytotoxic protein from the tissue of Trichosanthes kirilowii is also disclosed. The proteins may also be used within a method for inhibiting protein synthesis in selected cells.Type: GrantFiled: November 13, 1989Date of Patent: September 22, 1992Assignee: ZymoGenetics, Inc.Inventors: John M. Maraganore, Wayne R. Kindsvogel
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Patent number: 5149782Abstract: Molecular conjugates which facilitate the attachment of macromolecular drugs onto cellular surfaces and their entry into cells are described. The molecular conjugates comprise a macromolecular drug linked to an "inactivated" membrane blending agent which inserts into the cellular plasma membrane. The membrane blending agent is inactivated by cleavable linkage to a blocking agent which, until released from the conjugate under appropriate conditions, blocks and ability of the membrane blending agent to insert into the cellular membrane. Upon release of the blocking agent, the membrane blending agent is "activated" and the conjugate can be inserted into a cellular plasma membrane. The membrane blending agents can be peptides such as fusogenic or ion channel forming peptides or long chain fatty acids. The blocking agents can be bulky or charged moieties which mask and prevent insertion of the membrane blending agent.Type: GrantFiled: August 19, 1988Date of Patent: September 22, 1992Assignee: Tanox Biosystems, Inc.Inventors: Tse-wen Chang, Jean deVilliers, Wayne Gordon
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Patent number: 5144011Abstract: A method for controlling the release of durgs or other passenger molecules form carrier conjugates, and a class of conjugates that releases drugs when ingested by a cell or subjected to acidic conditions, are disclosed. These conjugates contain a passenger molecule which is attached to a spacer molecule through an acidic bonding group, such as carboxyl, that is in a "cis" configuration with another acidic group, and a carrier molecule that is bonded to the spacer molecule at another site. When subjected to a mild increase in acidity, such as occurs within a lysosome of a cell, the drug or other passenger molecule is hydrolyzed from the the conjugate and released in unmodified, active form.Type: GrantFiled: February 6, 1989Date of Patent: September 1, 1992Assignee: Boston UniversityInventors: Wei C. Shen, Hugues J.-P. Ryser
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Patent number: 5144009Abstract: The present invention relates to conjugates in which a monovalent carboxylic ionophore is associated by means of a covalent bond with a macromolecule chosen from antibodies, fragments of antibodies, proteins such as peptide hormones or human proteins, and peptide ligands. It also relates to the activated inophores.These conjugates are suitable as immunotoxin potentiators.Type: GrantFiled: December 28, 1989Date of Patent: September 1, 1992Assignee: SanofiInventors: Franz Jansen, Pierre Gros
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Patent number: 5140013Abstract: The present invention relates to anti-tumor-conjugation agent-protein compounds of the general formula I: ##STR1## wherein, R.sub.1 and R.sub.2 are each independently selected from hydrogen atom, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-6 carboxyalkyl, phenyl, or phenyl substituted by at least one of hydroxy, halogen, lower alkyl, lower alkoxy, or nitro, with the proviso that R.sub.1 and R.sub.2 cannot be simultaneously a hydrogen, and when one of R.sub.1 or R.sub.2 is a hydrogen, the other one cannot be --CH.sub.2 COOH;A is the residue of an anti-tumor agent containing at least one amino group available to form an amide bound; andB is a free .epsilon.-lysine containing residue selected from a peptide or a protein.Type: GrantFiled: November 28, 1989Date of Patent: August 18, 1992Assignee: Universite LavalInventors: Rene C. Gaudreault, Colette Mongrain
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Patent number: 5136027Abstract: A high concentration of renaturing surfactants is added to protein systems in the presence of alkyl sulfate detergents to displace the detergent with respect to the interaction with the protein, thereby renaturing the protein and restoring its reactivity. The presence of higher quantities of detergent in the system results in smaller protein aggregates, and thus a higher reactivity and specificity as measured for the system in its entirety.Type: GrantFiled: May 2, 1989Date of Patent: August 4, 1992Assignee: Abbott LaboratoriesInventor: Mark R. Pope
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Patent number: 5134071Abstract: A method for producing a polyprotein having at least 10 units, and often as many as 50 to 100 and more units held together by sulfur to sulfur or sulfur to carbon bonds is disclosed. Each unit comprises a protein and one or more heterobifunctional reagents. One functional group of the reagent is capable of forming a covalent bond with an amino group, permitting the reagent to bind to a protein. The other functional group of the reagent is capable of forming a covalent bond with a thiol group so as to form the covalent sulfur-carbon or sulfur-sulfur bond with another heterobifunctional reagent bonded to another protein.Type: GrantFiled: February 6, 1989Date of Patent: July 28, 1992Assignee: State University of New YorkInventor: Eric Gaetjens
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Patent number: 5128119Abstract: A method for radiolabeling a protein with a radioisotope of technetium of rhenium comprises the steps of contacting a solution of a protein containing a plurality of adjacent free sulfhydryl groups, or in particular cases, intact protein containing at least one disulfide group, with stannous ions, and then with radiopertechnetate or radioperrhenate, the amount of stannous ion being sufficient to substantially completely reduce the radiopertechnetate or radioperrhenate, and recovering radiolabeled protein.Type: GrantFiled: August 10, 1989Date of Patent: July 7, 1992Assignee: Immunomedics, Inc.Inventor: Gary L. Griffiths
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Patent number: 5124438Abstract: Chemically modified proteins obtainable by reacting casein, collagen, gelatin, albumin or mixtures thereof(a) with 0.5 to 15% by weight of chlorine or of a compound which liberates chlorine under the reaction conditions, in an aqueous medium at a pH of from 0 to 7 or(b) with 0.5 to 50% by weight of a non-aromatic mono- or disulfonic acid which contains in its organic radical one or more groups or structural features which react with nucleophiles, in an aqueous medium at a pH of from 6 to 14,are used as dispersants in colorant formulations.Type: GrantFiled: January 12, 1990Date of Patent: June 23, 1992Assignee: BASF AktiengesellschaftInventors: Ralf Brueckmann, Johannes P. Dix, Manfred Herrmann, Herbert Leiter, Norbert Zimmermann
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Patent number: 5122368Abstract: The invention relates to anthracycline conjugates comprising at least one anthracycline molecule linked to a molecule that is reactive with a cell population to be eliminated such as antibody, bombesin, EGF and transferrin. Each anthracycline molecule, having a keto group at the C-13 position, is conjugated to the antibody via a linker arm and is bound to that linker arm via an acid-sensitive acylhydrazone bond at the 13-keto position of the anthracycline. The linker additionally contains a disulfide or thioether linkage as part of the antibody or ligand attachment to the immunoconjugate. The novel anthracycline acylhydrazone derivatives are useful in the preparation of the conjugates of this invention. The acid-sensitive hydrazone bond of the conjugates of this invention allows the release of free anthracycline from the conjugates in the acidic external or internal environment of the target cell.Type: GrantFiled: May 17, 1989Date of Patent: June 16, 1992Assignee: Bristol-Myers Squibb CompanyInventors: Robert S. Greenfield, Gary R. Braslawsky, Lee J. Olech, Takushi Kaneko, Peter A, Kiener
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Patent number: 5112953Abstract: Chelating compounds of specified structure are useful for radiolabeling targeting molecules such as antibodies. Cleavable linkers connect the radionuclide metal chelates to the antibodies. The radiolabeled antibodies have improved biodistribution properties, including reduced localization within the intestines and kidneys.Type: GrantFiled: December 29, 1989Date of Patent: May 12, 1992Assignee: NeoRx CorporationInventors: Linda M. Gustavson, Ananthachari Srinivasan, Sudhakar Kasina, John M. Reno, Jeffrey N. Fitzner, David S. Jones
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Patent number: 5106955Abstract: A process for production of antibody conjugates which comprises modification of a part of the amino groups in an antibody or its fragment whose antigen-binding activity is lowered by the modification of its amino groups, with a reversible modifier for protein amino groups, reaction of the antibody or its fragment with a substance bearing a group reactive with the amino group and removal of the residues of the reversible modifier from the amino groups and, when necessary, the residues of the substance bearing a group reactive with the amino group in case they are introduced onto groups other than amino groups. The process according to the present invention gives antibody conjugates with retention of antigen-binding activity and these conjugates have a possibility of being used in affinity chromatography or as a diagnostic agent or a drug for cancer therapy.Type: GrantFiled: November 23, 1988Date of Patent: April 21, 1992Assignee: Teijin LimitedInventors: Noriaki Endo, Yumiko Takeda, Yoshinori Kato, Takeshi Hara
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Patent number: 5098733Abstract: Gel-like food article that has satisfactory functional characteristics such as high heat and acid resistance and yet which is safe to eat, and a process for producing this gel-like food article by crosslinking primary amino groups in food ingredients such as chitosan and proteins with an iridoid compound, which crosslinking may be combined with other methods of gelation.Type: GrantFiled: August 5, 1991Date of Patent: March 24, 1992Assignee: Suntory LimitedInventors: Nobuo Kyogoku, Keiko Harada
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Patent number: 5099000Abstract: A substituted monoethylglycinexylidide or analogue is disclosed. The xylidide or analogue has the structure of FIG. 1 of the attached drawings where M is CH.sub.2 NHCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 or CH.sub.2 OCH.sub.2 CH.sub.3, one of Y.sup.1 and Y.sup.2 is H and the other is a protein or a fluorescein moiety chemcially bonded to the glycinexylidide or analogue moiety. Also disclosed is a method for carrying out immunoassays for MEGX, which has the structure of FIG. 3 of the attached drawings. The method for carrying out immunoassays involves using the foregoing compounds as tracers and immunogens.Type: GrantFiled: December 22, 1989Date of Patent: March 24, 1992Assignee: Abbott LaboratoriesInventors: Lawrence Kolaczkowski, Mark Littlefield
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Patent number: 5095097Abstract: The invention relates to magnetic protein conjugates of the formula IM--NH--CO--(CH.sub.2).sub.n --S--P' Iwith n=1-6, preferably with a n=1 or 2 and particularly preferably with n=1, in which M is a dispersible, magnetically reacting material or particle which carries amino groups, and P' is a protein, to a process for the preparation thereof and to the use thereof for the specific removal of cells or soluble antigens, receptors, substrates, cofactors or carbohydrate determinants from aqueous salt solutions or body fluids or as part of a diagnostic method or as a diagnostic aid, preferably for the removal of cells, preferably for bone marrow depletion or for HLA typing.Type: GrantFiled: June 15, 1990Date of Patent: March 10, 1992Assignee: Behringwerke AktiengesellschaftInventors: Peter Hermentin, Reiner Donges, Udo Franssen, Karlheinz Enssle, Heinz-Jurgen Friesen
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Patent number: 5094950Abstract: A compound of the formula II: ##STR1## wherein n is an integer of 2 to 10, A' is a bivalent linking group formed by reacting both the reactive groups of a cross linking reagent, andB is a residue of a polypeptide compound, and physiologically acceptable salts thereof are disclosed. Such compound is useful as a non-radioactive carrier for radioactive metal elements.Type: GrantFiled: June 5, 1989Date of Patent: March 10, 1992Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Susumu Kondo, Miki Kurami, Makoto Azuma
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Patent number: 5094849Abstract: A series of antibody-vinca drug conjugates comprise antibodies which target antigens associated with undesirable cells, so that the cells are controlled or killed by the cytotoxic vinca drug. The drug is linked to the antibody through an organic group comprising a carbonyl at the antibody end, and an alkylidene hydrazide at the vinca end.Type: GrantFiled: January 14, 1991Date of Patent: March 10, 1992Assignee: Eli Lilly and CompanyInventors: George J. Cullinan, Bennett C. Laguzza, William L. Scott
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Patent number: 5093475Abstract: Novel compounds and methods for the formation of disulfide linkages are presented. The novel compounds employed are substituted 2-iminothiolane hydrohalide linking agents of the following formula (I): ##STR1## wherein, X is halogen;R.sub.1 is COOR.sub.5 ; halogen; nitro; unsubstituted or halogenated C.sub.1-8 alkyl; unsubstituted or halogenated C.sub.1-8 alkoxy; unsubstituted or halogenated C.sub.2-8 alkenyl; unsubstituted or halogenated C.sub.2-8 alkynyl; unsubstituted C.sub.3-8 cycloalkyl; unsubstituted aryl; aryl substituted with 1 to 3 substituents selected from halogen, amino, unsubstituted or halogenated C.sub.1-8 alkyl, or unsubstituted or halogenated C.sub.1-8 alkoxy; unsubstituted heterocycle; or heterocycle substituted with 1 to 3 substituents selected from amino, halogen, unsubstituted or halogenated C.sub.1-8 alkyl, or unsubstituted or halogenated C.sub.1-8 alkoxy;each of R.sub.2, R.sub.3 and R.sub.4 is independently hydrogen or selected from the values of R.sub.1 ; orR.sub.1 and R.sub.Type: GrantFiled: December 21, 1989Date of Patent: March 3, 1992Assignee: Xoma CorporationInventors: Stephen F. Carroll, Dane A. Goff
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Patent number: 5087616Abstract: A therapeutic composition comprising a chemical conjugatge including a first moiety, other than an immunoglobulin or fragment thereof, such as epidermal growth factor, which preferentially binds to a tumor cell, and is internalized by the cell, and a second moiety linked to the first moiety, and comprising a biodegradable polymeric carrier, such as polyglutamic acid, to which one or more cytotoxic molecules, for instance, daunomycin, are attached. The degradation of the carrier by intracellular enzymes releases a cytotoxic agent, resulting in selective destruction of the tumor cells.Type: GrantFiled: August 6, 1987Date of Patent: February 11, 1992Assignee: Battelle Memorial InstituteInventors: Andre E. Myers, Daniel Bichon
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Patent number: 5084559Abstract: The subject invention concerns novel protein A or protein A-like molecules that can be coupled to other materials through a single, defined site on the protein A molecule. Specifically exemplified is Cysteinyl-rProtein A.TM.. The compounds of the invention, for example, Cysteinyl-rProtein A.TM., can be used in processes wherein protein A is used.Type: GrantFiled: March 27, 1987Date of Patent: January 28, 1992Assignee: Repligen CorporationInventor: Albert T. Profy
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Patent number: 5077392Abstract: The present invention provides a process for the activation of gene-technologically produced, biologically active proteins expressed in prokaryotes after cell digestion by solubilization under denaturing conditions and reducing conditions and subsequent reactivation under oxidizing and renaturing conditions, wherein working is carried out at a protein concentration of 1 to 1000 .mu.g./ml. and, between the solubilization and the reactivation, a dialysis is carried out against a buffer with a pH value of from 1 to 4 containing 4 to 8 mole/liter guanidine hydrochloride or 6 to 10 mole/liter urea.Type: GrantFiled: October 17, 1989Date of Patent: December 31, 1991Assignee: Boehringer Mannheim GmbHInventors: Rainer Rudolph, Johannes Buchner, Helmut Lenz
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Patent number: 5073629Abstract: A fluorescence polarization immunoassay for detecting the presence of methadone in a test sample is provided, based upon competition between methadone and a fluorescently labeled tracer for the binding sites on an antibody specific for methadone. The concentration of methadone in the sample determines the amount of tracer that binds to the antibody. The amount of tracer-antibody complex formed can be quantitatively measured and is inversely proportional to the quantity of methadone in the sample. Tracers used as reagents and immunogens used to raise antibodies for use as reagents are also disclosed.Type: GrantFiled: January 23, 1989Date of Patent: December 17, 1991Assignee: Abbott LaboratoriesInventors: Robert E. Dubler, Susan A. Thacker, John A. Walling, Nai-Yi Wang
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Patent number: 5064767Abstract: Polypeptides are sequenced from the carboxyl terminus by treating the peptide with an iodoxybenzene, followed by removal of the excess reagent and reaction with 2-aminothiophenol at an elevated temperature. The resulting benzthiazolidine is then analyzed to determine the C-terminal amino acid which has been cleaved. A kit which contains the iodoxybenzene and 2-aminothiophenol reagents is separate containers is also disclosed.Type: GrantFiled: June 21, 1990Date of Patent: November 12, 1991Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Dean A. Le, Kazuhiko Tatemoto
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Patent number: 5061790Abstract: A method for conferring or increasing the antigenicity of a disulfide-crosslinked protein by treating the protein with an oxidizing agent, such as periodate, having an oxidation potential sufficient to cleave disulfide linkages. Excess oxidizing agent is then inactivated by addition of a reducing agent. The resulting protein exhibits an increase in its ability to be bound by select antibodies, particularly monoclonal antibodies directed to linear peptide epitopes in the protein.Type: GrantFiled: July 10, 1989Date of Patent: October 29, 1991Assignee: Molecular Diagnostics, Inc.Inventors: James J. Elting, Heinz Kolbl
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Patent number: 5061641Abstract: A protein containing at least one pendant sulfhydryl group is directly radiolabeled with a radiometal which binds tightly to sulfhydryl groups, using one or more pendant sulfhydral groups on the protein as endogenous ligands and optionally using an exogenous ligand which binds tightly to the radiometal ion to further stabilize the chelate.Type: GrantFiled: April 1, 1988Date of Patent: October 29, 1991Assignee: Immunomedics, Inc.Inventors: Dan Shochat, Hans J. Hansen, Robert S. Wu
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Patent number: 5061626Abstract: The invention concerns antigens for the production of antibodies to Platelet Activating Factor (PAF). The antigens are PAF analogues of formula (I) ##STR1## wherein X comprises a high molecular weight group, R.sup.1 is a linking group and R.sup.2 to R.sup.5 are selected from C.sub.1 to C.sub.6 alkyl.Other aspects of the invention include PAF-antibodies produced using said antigens, labelled PAF analogues, intermediates for the preparation of PAF analogues and methods and a kit for the immunoassay of PAF.Type: GrantFiled: November 24, 1987Date of Patent: October 29, 1991Assignee: University of SydneyInventors: Brian A. Baldo, John W. Redmond
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Patent number: RE34271Abstract: A high yield method of production of a cross-linked hemoglobin derivative suitable for use as a blood substitute and plasma expander which is cross-linked between Lys 99 Alpha.sub.1 and Lys 99 Alpha.sub.2 in high percentage by adding the cross-linker in the presence of an added polyanion which blocks competing reactions at other sites of the protein.Type: GrantFiled: May 24, 1990Date of Patent: June 1, 1993Assignee: University of Iowa Research FoundationInventor: Joseph A. Walder