ES2660594T3 - Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina - Google Patents
Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina Download PDFInfo
- Publication number
- ES2660594T3 ES2660594T3 ES09800657.0T ES09800657T ES2660594T3 ES 2660594 T3 ES2660594 T3 ES 2660594T3 ES 09800657 T ES09800657 T ES 09800657T ES 2660594 T3 ES2660594 T3 ES 2660594T3
- Authority
- ES
- Spain
- Prior art keywords
- oligosaccharide
- oligosaccharides
- methods
- groups
- compositions related
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/6415—Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/02—Bacterial antigens
- A61K39/085—Staphylococcus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/646—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/12—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria
- C07K16/1203—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria from Gram-negative bacteria
- C07K16/1228—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria from Gram-negative bacteria from Enterobacteriaceae (F), e.g. Citrobacter, Serratia, Proteus, Providencia, Morganella, Yersinia
- C07K16/1232—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria from Gram-negative bacteria from Enterobacteriaceae (F), e.g. Citrobacter, Serratia, Proteus, Providencia, Morganella, Yersinia from Escherichia (G)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/12—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria
- C07K16/1267—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria from Gram-positive bacteria
- C07K16/1271—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from bacteria from Gram-positive bacteria from Micrococcaceae (F), e.g. Staphylococcus
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N5/00—Undifferentiated human, animal or plant cells, e.g. cell lines; Tissues; Cultivation or maintenance thereof; Culture media therefor
- C12N5/06—Animal cells or tissues; Human cells or tissues
- C12N5/0602—Vertebrate cells
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N5/00—Undifferentiated human, animal or plant cells, e.g. cell lines; Tissues; Cultivation or maintenance thereof; Culture media therefor
- C12N5/10—Cells modified by introduction of foreign genetic material
- C12N5/12—Fused cells, e.g. hybridomas
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/55—Medicinal preparations containing antigens or antibodies characterised by the host/recipient, e.g. newborn with maternal antibodies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/55—Medicinal preparations containing antigens or antibodies characterised by the host/recipient, e.g. newborn with maternal antibodies
- A61K2039/552—Veterinary vaccine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/57—Medicinal preparations containing antigens or antibodies characterised by the type of response, e.g. Th1, Th2
- A61K2039/575—Medicinal preparations containing antigens or antibodies characterised by the type of response, e.g. Th1, Th2 humoral response
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
- A61K2039/6031—Proteins
- A61K2039/6037—Bacterial toxins, e.g. diphteria toxoid [DT], tetanus toxoid [TT]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K2317/00—Immunoglobulins specific features
- C07K2317/30—Immunoglobulins specific features characterized by aspects of specificity or valency
- C07K2317/33—Crossreactivity, e.g. for species or epitope, or lack of said crossreactivity
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Mycology (AREA)
- Toxicology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biophysics (AREA)
- Cell Biology (AREA)
- General Engineering & Computer Science (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Una composición que comprende un conjugado de oligosacárido-vehículo que comprende un oligosacárido conjugado a un vehículo a través de un enlazador que es **(Ver fórmula)** o **(Ver fórmula)** en las que n es mayor de 1, m es un número seleccionado de 1 a 10, p es un número seleccionado de 1 a 20 y R es H o un grupo alquilo, y en donde el enlazador está O-enlazado al oligosacárido y N-enlazado al vehículo, y en donde la composición es capaz de estimular una respuesta inmunitaria.
Description
Se pretende que los oligosacáridos de la invención imiten regiones de PNAG o dPNAG. De este modo, cuando se utilizan in vivo, los conjugados de oligosacárido-vehículo inducen respuestas inmunitarias dirigidas a regiones del oligosacárido que son similares o idénticas a PNAG y/o dPNAG y, por tanto, dichas respuestas inmunitarias son
5 útiles para dirigirse a especies bacterianas que fabrican o son capaces de fabricar PNAG y/o dPNAG.
En algunos aspectos de la invención, los oligosacáridos comprenden solamente unidades de D-glucosamina, o solamente N-acetil-D-glucosamina, o una relación predeterminada y orden de ambos tipos de estos monómeros. Se pretende que la relación y el orden imiten, en algunas realizaciones, las relaciones y órdenes que se encuentran en
10 un PNAG natural. Los oligosacáridos se manipulan de acuerdo con la invención para comprender un separador (o un enlazador, ya que los términos se usan de manera indistinta en el presente documento) que tienen un grupo tiol en su extremo (por ejemplo, su extremo reductor).
La preparación de oligosacáridos comprende grupos amino, tal como oligosacáridos de glucosamina unidos (u
15 oligoglucosaminas, ya que los términos se usan de manera indistinta en el presente documento) para su conjugación con uno o más vehículos, ha supuesto un desafío en la técnica. Esto se debe parcialmente a que la síntesis estereoespecífica de la glucosamina unida requiere el uso de grupos acilo N protectores participantes pero temporales (los denominados "grupos participantes") de los donantes de glicosilo para formar el necesario enlace βglucósido entre los monómeros. N-ftaloilo, N-tricloroetoxicarbonilo y algunos otros restos son adecuados como
20 grupos participantes. Sin embargo, algunos otros grupos participantes son menos adecuados incluidos los grupos participantes de N-acetilo que están presentes en algunos de los oligosacáridos considerados en la invención. A modo de ejemplo, los donantes de glicosilo N-acetilados son de baja reactividad y proporcionan solamente bajos rendimientos de productos de glicosilación. Además, la presencia de grupos N-acetilo en el donante de glicosilo complica la reacción de glicosilación debido a la formación del intermedio oxazolina, la migración de los grupos N
25 acetilo, y otras reacciones químicas indeseables.
Con respecto a las glucosaminas unidas, su estructura y, más especialmente, el número de grupos amino que contienen, requiere la introducción del enlazador antes de la liberación total de los grupos amino. La eliminación de los grupos protectores de N temporales anteriormente mencionados para preparar el oligosacárido libre se lleva a
30 cabo en condiciones básicas. El reactivo más eficaz para eliminar un grupo participante de N-ftaloilo es el hidrato de hidrazina en etanol en ebullición. Este reactivo también es eficaz para eliminar los grupos protectores de O-acilo incluidos los grupos acetilo y benzoílo que pueden estar incluidos en el oligosacárido de interés.
Los ligandos comercialmente disponibles que se han usado para la unión de ligandos que contienen grupos amino a
35 proteínas son S-acetiltioglicolato de pentafluorofenilo (estructura química 8 mostrada en los Ejemplos) y acetilsulfanil-propionato de N-hidroxisuccinimidilo 3 (estructura química 12 mostrada en los Ejemplos). Estos reactivos enlazadores se pueden usar para introducir un resto tiol en un oligosacárido; sin embargo, como se describe con mayor detalle en los Ejemplos, ambos son inestables en las condiciones de eliminación de los grupos ftaloilo. El Ejemplo 5 muestra que un enlazador basado en ácido tioglicólico experimenta reordenamiento oxidativo, y
40 el Ejemplo 6 muestra que un derivado del ácido 3-mercaptopropiónico proporciona una mezcla compleja de productos secundarios. Ambas transformaciones dan como resultado la pérdida de la necesaria función tiol.
Por tanto, la invención se basa en parte en el descubrimiento y el uso de una clase de enlazadores que es eficaz y mejor que los enlazadores anteriormente conocidos para conjugar oligosacáridos (incluidas las versiones que
45 contienen amina de los mismos) con un vehículo tal como una proteína. Esta clase de enlazadores se define como derivados del ácido ω-acetilsulfanil carbónico de Fórmula I (donde n > 1).
Fórmula I
50 Esta clase de enlazadores proporciona una N-acilación eficaz durante la unión a un oligosacárido. El enlazador puede ser un éster activo de Fórmula I o su derivado ciano, azido, o haloide. Puede haber otro derivado de Fórmula I siempre que dicho derivado sea activo como agente acilante y por tanto adecuado para su unión a los oligosacáridos de la presente invención. Y representa un grupo bloqueante temporal de átomos de azufre, que son conocidos en la
55 técnica y que incluyen grupos acilo y acetilo. La eliminación del grupo Y libera un grupo SH que es necesario para la unión del oligosacárido al vehículo. X representa cualquier grupo saliente que proporcione la capacidad acilante necesaria al compuesto de Fórmula I.
Se entenderá que cualquiera de las clases de enlazadores proporcionadas por la invención se puede usar para 60 conjugar los oligosacáridos con los compuestos vehículo. A modo de ejemplo, una clase de enlazador puede comprender la estructura de Fórmula II (donde n > 1):
8
Claims (1)
-
imagen1 imagen2 imagen3
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US135493P | 1999-05-24 | ||
US13549308P | 2008-07-21 | 2008-07-21 | |
US20815509P | 2009-02-20 | 2009-02-20 | |
US208155P | 2009-02-20 | ||
PCT/US2009/004206 WO2010011284A2 (en) | 2008-07-21 | 2009-07-21 | Methods and compositions relating to synthetic beta-1,6 glucosamine oligosaccharides |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2660594T3 true ES2660594T3 (es) | 2018-03-23 |
Family
ID=41570770
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES09800657.0T Active ES2660594T3 (es) | 2008-07-21 | 2009-07-21 | Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina |
Country Status (19)
Country | Link |
---|---|
US (5) | US8492364B2 (es) |
EP (2) | EP3312158A1 (es) |
JP (1) | JP5555230B2 (es) |
KR (4) | KR20110031393A (es) |
CN (2) | CN105085349B (es) |
AU (1) | AU2009274630B2 (es) |
BR (1) | BRPI0916365A2 (es) |
CA (1) | CA2731384C (es) |
CO (1) | CO6341620A2 (es) |
DK (1) | DK2315747T3 (es) |
ES (1) | ES2660594T3 (es) |
HK (1) | HK1254488A1 (es) |
IL (2) | IL210789A (es) |
MX (2) | MX2011000823A (es) |
NZ (1) | NZ591103A (es) |
PT (1) | PT2315747T (es) |
RU (1) | RU2532911C2 (es) |
WO (1) | WO2010011284A2 (es) |
ZA (1) | ZA201101000B (es) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2003295520B8 (en) | 2002-11-12 | 2011-05-19 | The Brigham And Women's Hospital, Inc. | Polysaccharide vaccine for Staphylococcal infections |
ES2415358T3 (es) | 2004-04-21 | 2013-07-25 | The Brigham And Women's Hospital, Inc. | Péptidos de fijación a la poli-N-acetil glucosamina (PNAG/DPNAG) y procedimientos para el uso de los mismos |
RU2532911C2 (ru) | 2008-07-21 | 2014-11-20 | Дзе Брихэм Энд Уимен'З Хоспитал, Инк. | Способы и композиции, относящиеся к синтетическим бета-1,6-глюкозаминолигосахаридам |
US20130116423A1 (en) | 2010-04-23 | 2013-05-09 | A. Stewart Campbell | Synthetic Oligosaccharides for Staphylococcus Vaccine |
FR2967677B1 (fr) * | 2010-11-18 | 2014-05-16 | Centre Nat Rech Scient | Derives de polysaccharides comprenant un motif alcene et reaction de couplage par chimie thio-clic |
WO2012145626A1 (en) * | 2011-04-22 | 2012-10-26 | Ancora Pharmaceuticals Inc. | Synthetic oligosaccharides for staphylococcus vaccine |
RU2014152261A (ru) | 2012-05-30 | 2016-07-20 | Дзе Брихэм Энд Уимен'З Хоспитал, Инк. | Композиции полисахаридов и способы применения |
EP2968427B1 (en) | 2013-03-12 | 2022-10-26 | Wellstat Vaccines, Llc | Conjugate for inducing antibodies targeting fungal cell wall polysaccharides |
US9597433B2 (en) | 2013-08-23 | 2017-03-21 | University Of Houston System | Non-pathogenic biofilms and uses thereof |
SG11201901394XA (en) | 2016-09-02 | 2019-03-28 | Sanofi Pasteur Inc | Neisseria meningitidis vaccine |
WO2021041721A1 (en) * | 2019-08-27 | 2021-03-04 | OneBioPharma, Inc. | Antimicrobial vaccine compositions |
US11173199B2 (en) * | 2019-11-13 | 2021-11-16 | Alopexx Inc. | Low contaminant compositions |
KR20220107001A (ko) * | 2019-11-22 | 2022-08-01 | 알로펙스, 인크. | Pnag 포함 미생물에 대한 연속 치료를 제공하는 방법 |
US10828360B1 (en) | 2020-02-04 | 2020-11-10 | OneBioPharma, Inc. | Methods for inhibiting biofilm formation |
CN112920237B (zh) * | 2021-01-27 | 2022-06-14 | 山东大学 | 一种糖基受体、酶法合成寡糖链的快速分离的方法及应用 |
WO2022189361A1 (en) * | 2021-03-08 | 2022-09-15 | Universiteit Gent | Conjugates including multiple saccharidic chains on a linear protein and uses in mammals feed |
Family Cites Families (106)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US565354A (en) | 1896-08-04 | James h | ||
US2842049A (en) | 1954-09-22 | 1958-07-08 | Technicolor Corp | Deacetylated chitin mordant |
JPS5452794A (en) | 1977-09-30 | 1979-04-25 | Kousaku Yoshida | Extracting of polysacchride from capusle containing epidermis staphylococus |
US4285936A (en) | 1979-12-10 | 1981-08-25 | The United States Of America As Represented By The Secretary Of The Army | Method for producing a vaccine against bacterial infections caused by pseudomonas aeruginosa |
JPS5686121A (en) | 1979-12-14 | 1981-07-13 | Teijin Ltd | Antitumor proten complex and its preparation |
US4355023A (en) | 1980-09-30 | 1982-10-19 | The Massachusetts General Hospital | Antibody fragment compositions and process |
US4443549A (en) | 1981-10-19 | 1984-04-17 | Molecular Genetics, Inc. | Production of monoclonal antibodies against bacterial adhesins |
US4470925A (en) | 1982-05-05 | 1984-09-11 | E. I. Du Pont De Nemours And Company | Immunoglobulin half-molecules and process for producing hybrid antibodies |
US4462334A (en) | 1982-08-19 | 1984-07-31 | Kim Ho K | Solar animal structure |
US4465776A (en) | 1982-09-27 | 1984-08-14 | Research Corporation | Monoclonal antibodies to vitamin B6 and immunoassay method |
US4652448A (en) | 1982-10-07 | 1987-03-24 | Molecular Genetics, Inc. | Use of monoclonal antibodies against bacterial adhesins |
US4578458A (en) | 1983-03-23 | 1986-03-25 | Brigham And Women's Hospital | Mucoid exopolysaccharide vaccine against Pseudomonas aeruginosa |
DK219084D0 (da) | 1984-05-02 | 1984-05-02 | Frederik Carl Peter Lindberg | Antigen |
JPS6191131A (ja) | 1984-10-09 | 1986-05-09 | Chugai Pharmaceut Co Ltd | 医薬品の吸着防止方法および組成物 |
GB8426463D0 (en) | 1984-10-19 | 1984-11-28 | Technology Licence Co Ltd | Monoclonal antibodies |
NZ214503A (en) | 1984-12-20 | 1990-02-26 | Merck & Co Inc | Covalently-modified neutral bacterial polysaccharides, stable covalent conjugates of such polysaccharides and immunogenic proteins, and methods of preparing such polysaccharides and conjugates |
FR2581877B1 (fr) | 1985-05-14 | 1987-12-18 | Louvain Universite Catholique | Conjugue constitue d'une adhesine de paroi de s. mutans, de nature proteique et d'un polysaccharide de s. mutans, sa preparation et son utilisation notamment dans des vaccins anti-caries |
US4755381A (en) | 1986-03-27 | 1988-07-05 | Swiss Serum And Vaccine Institute Berne | Klebsiella capsular polysaccharide vaccine |
GB8607679D0 (en) | 1986-03-27 | 1986-04-30 | Winter G P | Recombinant dna product |
US4786592A (en) | 1986-06-18 | 1988-11-22 | Scripps Clinic And Research Foundation | Neisseria gonorrhoeae lectin useful as a vaccine and diagnostic marker and means for producing this lectin |
US5589591A (en) | 1986-07-03 | 1996-12-31 | Advanced Magnetics, Inc. | Endotoxin-free polysaccharides |
US4946778A (en) | 1987-09-21 | 1990-08-07 | Genex Corporation | Single polypeptide chain binding molecules |
US5567610A (en) | 1986-09-04 | 1996-10-22 | Bioinvent International Ab | Method of producing human monoclonal antibodies and kit therefor |
GB8621910D0 (en) | 1986-09-11 | 1986-10-15 | Technology Licence Co Ltd | Monoclonal antibodies |
FR2619122B1 (fr) | 1987-08-03 | 1990-03-09 | Pasteur Institut | Procede d'obtention de polyosides capsulaires de staphylocoques, polyosides obtenus, applications de ces polyosides et souches pour la mise en oeuvre du procede |
US4859449A (en) | 1987-09-14 | 1989-08-22 | Center For Molecular Medicine And Immunology | Modified antibodies for enhanced hepatocyte clearance |
CA1340506C (en) | 1987-11-24 | 1999-04-20 | Nicholas H. Carbonetti | Production of gonorrheal pi proteins and vaccines |
US5204098A (en) | 1988-02-16 | 1993-04-20 | The United States Of America As Represented By The Department Of Health And Human Services | Polysaccharide-protein conjugates |
US5055455A (en) | 1988-09-28 | 1991-10-08 | Brigham And Women's Hospital | Capsular polysaccharide adhesin antigen, preparation, purification and use |
FR2640628A1 (fr) | 1988-12-16 | 1990-06-22 | Commissariat Energie Atomique | Oligosaccharides lies (beta)-(1 -> 6) en particulier des 2-acetamido-2-desoxy-glucoses ou - galactoses et leur preparation |
EP0449958B9 (en) | 1988-12-19 | 2003-05-28 | American Cyanamid Company | Meningococcal class 1 outer-membrane protein vaccine |
CA2039789A1 (en) | 1990-04-27 | 1991-10-28 | Samuel J. Danishefsky | Calicheamicinone, derivatives and analogs thereof and methods of making the same |
DK0546073T3 (da) | 1990-08-29 | 1998-02-02 | Genpharm Int | Frembringelse og anvendelse af transgene, ikke-humane dyr, der er i stand til at danne heterologe antistoffer |
US5571511A (en) | 1990-10-22 | 1996-11-05 | The U.S. Government | Broadly reactive opsonic antibodies that react with common staphylococcal antigens |
DE4219159A1 (de) * | 1992-06-11 | 1993-12-16 | Boehringer Mannheim Gmbh | Selbst assemblierende Monoschicht mit kurzkettigen Linkern |
US5763191A (en) | 1990-12-12 | 1998-06-09 | Boehringer Mannheim Gmbh | Universal binding film |
US5352670A (en) | 1991-06-10 | 1994-10-04 | Alberta Research Council | Methods for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides |
WO1993001276A1 (en) | 1991-07-12 | 1993-01-21 | Smithkline Beecham Corporation | Continuous cell line and vaccine against avian coccidia |
WO1993009811A1 (en) | 1991-11-22 | 1993-05-27 | Univax Biologics, Inc. | TYPE I AND TYPE II SURFACE ANTIGENS ASSOCIATED WITH $i(STAPHYLOCOCCUS EPIDERMIDIS) |
US5872215A (en) | 1991-12-02 | 1999-02-16 | Medical Research Council | Specific binding members, materials and methods |
EP0615458B1 (en) | 1991-12-06 | 1997-08-06 | North Shore University Hospital Research Corporation | Method of reducing medical device related infections |
PT635132E (pt) | 1992-03-19 | 2001-03-30 | Henry M Jackson Found Advanc M | Anticorpos opsonicos amplamente reactivos que reagem com antigenios de estafilococos comuns |
US5425946A (en) | 1992-08-31 | 1995-06-20 | North American Vaccine, Inc. | Vaccines against group C Neisseria meningitidis |
US5688516A (en) | 1992-11-12 | 1997-11-18 | Board Of Regents, The University Of Texas System | Non-glycopeptide antimicrobial agents in combination with an anticoagulant, an antithrombotic or a chelating agent, and their uses in, for example, the preparation of medical devices |
US5362754A (en) | 1992-11-12 | 1994-11-08 | Univ. Of Tx Md Anderson Cancer Center | M-EDTA pharmaceutical preparations and uses thereof |
JPH08508240A (ja) | 1993-01-12 | 1996-09-03 | ジョージ グリスティーナ,アンソニー | 受動免疫の直接的濃厚伝達のための方法および組成物 |
US5718694A (en) | 1993-11-09 | 1998-02-17 | The Board Of Regents Of The University Of Nebraska | Inhibition of adherence of microorganisms to biomaterial surfaces by treatment with carbohydrates |
US5858350A (en) | 1993-12-01 | 1999-01-12 | Marine Polymer Technologies | Methods and compositions for poly-β-1→4-N-acetylglucosamine cell therapy system |
RU2170257C2 (ru) | 1994-03-17 | 2001-07-10 | Мерк Патент Гмбх | Анти-эфрр одноцепочечный fv, химерное анти-эфрр антитело и способ его получения, фармацевтическая композиция для лечения опухолей, средство для диагностики локализации или оценки роста опухоли |
US5534615A (en) | 1994-04-25 | 1996-07-09 | Genentech, Inc. | Cardiac hypertrophy factor and uses therefor |
JPH0840932A (ja) | 1994-07-29 | 1996-02-13 | Kitasato Inst:The | スタフイロコッカス属菌感染症の予防ワクチン及び治療用抗体並びにそれの製造法 |
CA2168509A1 (en) | 1995-02-13 | 1996-08-14 | Gregory C. Stalcup | Orthopaedic milling guide with cutter lockout |
AU7339996A (en) | 1995-11-06 | 1997-05-29 | Chugai Seiyaku Kabushiki Kaisha | Sydnone imine derivatives |
US5830539A (en) | 1995-11-17 | 1998-11-03 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Methods for functionalizing and coating substrates and devices made according to the methods |
JP3372551B2 (ja) * | 1995-11-21 | 2003-02-04 | ノバルティス アクチエンゲゼルシャフト | 多価ポリマー、その製造方法、および生物学的に活性な化合物の製造におけるその使用 |
US6245735B1 (en) | 1996-07-29 | 2001-06-12 | The Brigham And Women's Hospital, Inc. | Methods and products for treating pseudomonas infection |
US6294177B1 (en) | 1996-09-11 | 2001-09-25 | Nabi | Staphylococcus aureus antigen-containing whole cell vaccine |
CZ106299A3 (cs) | 1996-09-26 | 1999-08-11 | Chugai Seiyaku Kabushiki Kaisha | Protilátky proti proteinu příbuznému s lidským parathyroidálním hormonem |
ATE332918T1 (de) | 1997-04-18 | 2006-08-15 | Novartis Pharma Gmbh | Neoglycoproteine |
US6235883B1 (en) | 1997-05-05 | 2001-05-22 | Abgenix, Inc. | Human monoclonal antibodies to epidermal growth factor receptor |
TW586934B (en) | 1997-05-19 | 2004-05-11 | Sumitomo Pharma | Immunopotentiating composition |
WO1999008705A1 (en) | 1997-08-20 | 1999-02-25 | Brigham And Women's Hospital | Capsular polysaccharides from enterococci |
IT1298539B1 (it) | 1998-02-03 | 2000-01-12 | Bracco Spa | Metodo per la determinazione di infezioni da protesi |
US7018637B2 (en) | 1998-02-23 | 2006-03-28 | Aventis Pasteur, Inc | Multi-oligosaccharide glycoconjugate bacterial meningitis vaccines |
CA2264970A1 (en) | 1998-03-10 | 1999-09-10 | American Cyanamid Company | Antigenic conjugates of conserved lipolysaccharides of gram negative bacteria |
EP1068312A2 (en) | 1998-04-09 | 2001-01-17 | Genset | 5' ests and encoded human proteins |
US7214487B2 (en) | 1998-06-26 | 2007-05-08 | Sunesis Pharmaceuticals, Inc. | Methods for identifying compounds that modulate enzymatic activities by employing covalently bonded target-extender complexes with ligand candidates |
AU4919699A (en) | 1998-07-11 | 2000-02-01 | Mhm Holdings Limited | Vehicle seat, vehicle seat table and vehicle communication system |
US7252828B2 (en) | 1998-07-15 | 2007-08-07 | The Brigham And Women's Hospital, Inc. | Polysaccharide vaccine for staphylococcal infections |
DK1096952T3 (da) | 1998-07-15 | 2008-08-25 | Brigham & Womens Hospital | Polysaccharidvaccine mod stafylokok-infektioner |
TNSN99243A1 (fr) | 1998-12-16 | 2001-12-31 | Sca Hygiene Prod Zeist Bv | Polysaccharides superabsorbants acides |
CA2365296A1 (en) | 1999-03-19 | 2000-09-28 | Pierre Michel Desmons | Vaccine |
AU2002309567A1 (en) | 2001-05-16 | 2002-12-03 | The Children's Hospital Of Philadelphia | Dna-antibody complexes to enhance gene transfer |
US7119172B2 (en) | 2001-05-21 | 2006-10-10 | The Brigham And Women's Hospital, Inc. | P. aeruginosa mucoid exopolysaccharide specific binding peptides |
WO2002094854A2 (en) | 2001-05-21 | 2002-11-28 | The Brigham And Women's Hospital, Inc. | P.aeruginosa mucoid exopolysaccharide specific binding peptides |
US20030113350A1 (en) | 2001-09-19 | 2003-06-19 | Fattom Ali I. | Glycoconjugate vaccines for use in immune-compromised populations |
CN1344722A (zh) | 2001-10-19 | 2002-04-17 | 北京盈富安信科技有限公司 | 1→6连接的氨基葡聚寡糖和糖苷及其合成和应用 |
JP2005538682A (ja) | 2001-12-03 | 2005-12-22 | アブジェニックス・インコーポレーテッド | カルボキシックアンヒドラーゼix(caix)腫瘍抗原に対する抗体 |
CA2469132A1 (en) | 2001-12-11 | 2003-07-03 | Merck & Co., Inc. | Staphylococcus aureus exopolysaccharide and process |
EP1470146B8 (en) | 2001-12-28 | 2007-09-12 | Amgen Fremont Inc. | Antibodies against the muc18 antigen |
CA2492671C (en) | 2002-03-22 | 2012-04-17 | Aprogen, Inc. | Humanized antibody and process for preparing same |
EP1497445A2 (en) | 2002-04-01 | 2005-01-19 | Human Genome Sciences, Inc. | Antibodies that specifically bind to gmad |
AU2003290867A1 (en) | 2002-11-12 | 2004-06-03 | The Brigham And Women's Hospital, Inc. | Methods and products for treating staphylococcal infections |
AU2003295520B8 (en) | 2002-11-12 | 2011-05-19 | The Brigham And Women's Hospital, Inc. | Polysaccharide vaccine for Staphylococcal infections |
JP5102487B2 (ja) | 2003-03-07 | 2012-12-19 | ワイス・ホールディングズ・コーポレイション | 院内感染に対する免疫化のための多糖ブドウ球菌表面付着因子キャリアタンパク質接合体 |
JP4764820B2 (ja) | 2003-06-23 | 2011-09-07 | バクスター・インターナショナル・インコーポレイテッド | ワクチン用担体タンパク質 |
US9928522B2 (en) | 2003-08-01 | 2018-03-27 | Oath (Americas) Inc. | Audience matching network with performance factoring and revenue allocation |
KR101270692B1 (ko) | 2003-08-12 | 2013-06-03 | 리폭센 테크놀로지즈 리미티드 | 폴리시알산 유도체 |
ES2415358T3 (es) | 2004-04-21 | 2013-07-25 | The Brigham And Women's Hospital, Inc. | Péptidos de fijación a la poli-N-acetil glucosamina (PNAG/DPNAG) y procedimientos para el uso de los mismos |
CA2475736A1 (en) * | 2004-07-23 | 2006-01-23 | Cyrille Grandjean | Vibrio cholerae lps detoxified derivatives and immunogenic compositions containing them |
US20080085289A1 (en) | 2004-09-22 | 2008-04-10 | Cindy Castado | Immunogenic Composition |
GB0426394D0 (en) | 2004-12-01 | 2005-01-05 | Health Prot Agency | Fusion proteins |
ES2539126T3 (es) * | 2004-12-09 | 2015-06-26 | Janssen Biotech, Inc. | Inmunoconjugados anti integrina, métodos para su producción y su uso |
US20060134141A1 (en) | 2004-12-14 | 2006-06-22 | Nabi Biopharmaceuticals | Glycoconjugate vaccines containing peptidoglycan |
CA2600696A1 (en) | 2005-03-14 | 2006-09-21 | Governors Of The University Of Alberta | Synthetic anti-candida albicans oligosaccharide based vaccines |
GB0505996D0 (en) * | 2005-03-23 | 2005-04-27 | Glaxosmithkline Biolog Sa | Fermentation process |
AR060188A1 (es) | 2006-03-30 | 2008-05-28 | Glaxosmithkline Biolog Sa | Procedimiento de conjugacion |
AU2007233705B2 (en) | 2006-03-30 | 2010-12-23 | Glaxosmithkline Biologicals S.A. | Immunogenic composition |
CA2653390C (en) | 2006-06-02 | 2014-07-08 | Hawaii Chitopure, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
CN100521341C (zh) | 2006-08-30 | 2009-07-29 | 三洋电机株式会社 | 燃料电池及燃料电池用燃料供给装置 |
RU2532911C2 (ru) | 2008-07-21 | 2014-11-20 | Дзе Брихэм Энд Уимен'З Хоспитал, Инк. | Способы и композиции, относящиеся к синтетическим бета-1,6-глюкозаминолигосахаридам |
EP2399595B1 (en) | 2009-02-20 | 2015-11-04 | Meisho.Co., Ltd | Immunopotentiating composition and process for producing same |
EA023397B1 (ru) | 2010-05-26 | 2016-05-31 | Селекта Байосайенсиз, Инк. | Комбинированные вакцины с синтетическими наноносителями |
WO2012099805A2 (en) | 2011-01-19 | 2012-07-26 | Ocean Nanotech, Llc | Nanoparticle based immunological stimulation |
RU2014152261A (ru) | 2012-05-30 | 2016-07-20 | Дзе Брихэм Энд Уимен'З Хоспитал, Инк. | Композиции полисахаридов и способы применения |
EP2948560B1 (en) | 2013-01-22 | 2019-07-03 | Imicroq, S.L. | Rapid method for detection of pathogen |
-
2009
- 2009-07-21 RU RU2011106332/04A patent/RU2532911C2/ru active
- 2009-07-21 EP EP17198371.1A patent/EP3312158A1/en active Pending
- 2009-07-21 MX MX2011000823A patent/MX2011000823A/es active IP Right Grant
- 2009-07-21 JP JP2011520030A patent/JP5555230B2/ja not_active Expired - Fee Related
- 2009-07-21 MX MX2014000756A patent/MX351810B/es unknown
- 2009-07-21 DK DK09800657.0T patent/DK2315747T3/en active
- 2009-07-21 KR KR1020117003763A patent/KR20110031393A/ko active Application Filing
- 2009-07-21 BR BRPI0916365A patent/BRPI0916365A2/pt not_active Application Discontinuation
- 2009-07-21 EP EP09800657.0A patent/EP2315747B1/en active Active
- 2009-07-21 CN CN201510412419.2A patent/CN105085349B/zh active Active
- 2009-07-21 WO PCT/US2009/004206 patent/WO2010011284A2/en active Application Filing
- 2009-07-21 AU AU2009274630A patent/AU2009274630B2/en not_active Ceased
- 2009-07-21 NZ NZ591103A patent/NZ591103A/xx not_active IP Right Cessation
- 2009-07-21 KR KR1020167020817A patent/KR101785373B1/ko active IP Right Grant
- 2009-07-21 KR KR1020147017111A patent/KR101573648B1/ko active IP Right Grant
- 2009-07-21 CN CN200980136515.1A patent/CN102159540B/zh active Active
- 2009-07-21 ES ES09800657.0T patent/ES2660594T3/es active Active
- 2009-07-21 KR KR1020157008121A patent/KR20150041178A/ko not_active Application Discontinuation
- 2009-07-21 PT PT98006570T patent/PT2315747T/pt unknown
- 2009-07-21 US US13/055,178 patent/US8492364B2/en active Active
- 2009-07-21 CA CA2731384A patent/CA2731384C/en active Active
-
2011
- 2011-01-20 IL IL210789A patent/IL210789A/en active IP Right Grant
- 2011-02-08 ZA ZA2011/01000A patent/ZA201101000B/en unknown
- 2011-02-18 CO CO11019519A patent/CO6341620A2/es active IP Right Grant
-
2013
- 2013-06-21 US US13/924,435 patent/US9474806B2/en active Active
-
2015
- 2015-11-22 IL IL242710A patent/IL242710B/en active IP Right Grant
-
2016
- 2016-09-07 US US15/258,417 patent/US10034927B2/en active Active
-
2018
- 2018-06-22 US US16/016,473 patent/US11123416B2/en active Active
- 2018-10-25 HK HK18113697.9A patent/HK1254488A1/zh unknown
-
2021
- 2021-08-20 US US17/408,287 patent/US20220175904A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES2660594T3 (es) | Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina | |
ES2740907T3 (es) | Enlazador de sulfamida, conjugados de los mismos y métodos de preparación | |
TWI733751B (zh) | 核酸複合體 | |
Virta et al. | Solid-supported synthesis of oligomeric bioconjugates | |
JP2005518201A (ja) | 生体分子の細胞取り込みを増強するためのリガンド | |
Hamzavi et al. | Modulation of the pharmacokinetic properties of PNA: preparation of galactosyl, mannosyl, fucosyl, N-acetylgalactosaminyl, and N-acetylglucosaminyl derivatives of aminoethylglycine peptide nucleic acid monomers and their incorporation into PNA oligomers | |
CA2080502A1 (en) | Method for producing synthetic n-linked glycoconjugates | |
JPH03500530A (ja) | 新規な両親媒性核酸接合体 | |
BRPI0614839A2 (pt) | fator vii e fator viia glicopeguilados | |
US7438900B2 (en) | Dendritic encapsulation of active agents | |
US20180193471A1 (en) | ß2GPI GENE EXPRESSION-SUPPRESSING NUCLEIC ACID CONJUGATE | |
US6320041B1 (en) | Pre-activated carbonyl linkers for the modification of oligonucleotides | |
Morais et al. | Glycosyl disulfides: importance, synthesis and application to chemical and biological systems | |
JP2001513089A (ja) | 保護されたアミノ糖 | |
ES2346506B1 (es) | "ciclooligoros anfifilicos policationicos y su uso como transportadores moleculares.". | |
CA2366681A1 (en) | Methods and compositions for the manufacture of c-3' and c-4' anthracycline antibiotics | |
WO2019027009A1 (ja) | 核酸複合体 | |
Gauthier et al. | Conjugation of Small Molecules to RNA Using a Reducible Disulfide Linker Attached at the 2′‐OH Position through a Carbamate Function | |
US20090036553A1 (en) | Dendritic encapsulation of active agents | |
EP3888663A1 (en) | Nucleic acid complex | |
Zatsepin et al. | Nucleosides and oligonucleotides containing 2'-reactive groups: synthesis and applications | |
JP2003212893A (ja) | アミド結合型糖鎖含有カルボシランデンドリマーおよびその製造方法 | |
ES2324137B2 (es) | Tiofucosidos conteniendo prolinas hidroxiladas. sintesis y usos de los mismos. | |
Lönnberg | 5 Natural polymers—chemistry | |
Singh et al. | dNa CONjUgatiON tO HaLOtaggEd pROtEiN UsiNg gLEN BROMOHExyL LiNkER |