CA2591232C - Glycolipids and analogues thereof as antigens for nk t cells - Google Patents

Glycolipids and analogues thereof as antigens for nk t cells Download PDF

Info

Publication number
CA2591232C
CA2591232C CA2591232A CA2591232A CA2591232C CA 2591232 C CA2591232 C CA 2591232C CA 2591232 A CA2591232 A CA 2591232A CA 2591232 A CA2591232 A CA 2591232A CA 2591232 C CA2591232 C CA 2591232C
Authority
CA
Canada
Prior art keywords
another embodiment
cells
compound
formula
cell
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.)
Expired - Fee Related
Application number
CA2591232A
Other languages
English (en)
French (fr)
Other versions
CA2591232A1 (en
Inventor
Chi-Huey Wong
Doug Wu
Masakazu Fujio
Moriya Tsuji
David Ho
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rockefeller University
Scripps Research Institute
Original Assignee
Rockefeller University
Scripps Research Institute
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rockefeller University, Scripps Research Institute filed Critical Rockefeller University
Publication of CA2591232A1 publication Critical patent/CA2591232A1/en
Application granted granted Critical
Publication of CA2591232C publication Critical patent/CA2591232C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
    • 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
    • A61P35/00—Antineoplastic 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
    • A61P37/02—Immunomodulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Saccharide Compounds (AREA)
CA2591232A 2004-12-28 2005-12-27 Glycolipids and analogues thereof as antigens for nk t cells Expired - Fee Related CA2591232C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US63940804P 2004-12-28 2004-12-28
US60/639,408 2004-12-28
PCT/US2005/047017 WO2006071848A2 (en) 2004-12-28 2005-12-27 Glycolipids and analogues thereof as antigens for nk t cells

Publications (2)

Publication Number Publication Date
CA2591232A1 CA2591232A1 (en) 2006-07-06
CA2591232C true CA2591232C (en) 2014-10-21

Family

ID=36615471

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2591232A Expired - Fee Related CA2591232C (en) 2004-12-28 2005-12-27 Glycolipids and analogues thereof as antigens for nk t cells

Country Status (6)

Country Link
US (2) US7534434B2 (cg-RX-API-DMAC10.html)
EP (1) EP1833489A4 (cg-RX-API-DMAC10.html)
JP (1) JP5090928B2 (cg-RX-API-DMAC10.html)
AU (1) AU2005322027B2 (cg-RX-API-DMAC10.html)
CA (1) CA2591232C (cg-RX-API-DMAC10.html)
WO (1) WO2006071848A2 (cg-RX-API-DMAC10.html)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9809654B2 (en) 2002-09-27 2017-11-07 Vaccinex, Inc. Targeted CD1d molecules
US7645873B2 (en) * 2003-03-20 2010-01-12 The Scripps Research Institute 6″-amino-6″-deoxygalactosylceramides
US20060269524A1 (en) * 2004-02-19 2006-11-30 Kibun Food Chemifa Co., Ltd. Composition for nkt cell activation
US7923013B2 (en) * 2004-12-28 2011-04-12 The Rockefeller University Glycolipids and analogues thereof as antigens for NKT cells
JP5090928B2 (ja) 2004-12-28 2012-12-05 ザ ロックフェラー ユニバーシティ Nkt細胞に対する抗原としての糖脂質及びその類似体
EP1940418B1 (en) * 2005-09-29 2011-01-19 Torrey Pines Institute For Molecular Studies Sulfatides for treatment of autoimmune disorders
WO2007118234A2 (en) 2006-04-07 2007-10-18 The Scripps Research Institute Modified -galactosyl ceramides for staining and stimulating natural killer t cells
WO2007137258A2 (en) * 2006-05-22 2007-11-29 New York University C-glycolipids with enhanced th-1 profile
AU2007269299B2 (en) * 2006-06-30 2013-01-17 Brigham Young University Adjuvants and methods of use
EP2112930B1 (en) * 2007-02-21 2017-01-11 Vaccinex, Inc. Modulation of nkt cell activity with antigen-loaded cdid molecules
US7960139B2 (en) 2007-03-23 2011-06-14 Academia Sinica Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells
WO2008128207A1 (en) * 2007-04-13 2008-10-23 Academia Sinica Alpha-galactosyl ceramide analogs and their use as immunotherapies
WO2008133983A1 (en) * 2007-04-25 2008-11-06 Immurx, Inc. Adjuvant combinations of nkt activator, cd40 agonist, and optional antigen, the use through inducing synergistic cellular immunity
US8916164B2 (en) * 2007-08-29 2014-12-23 Abivax Methods of enhancing adjuvaticity of vaccine compositions
EP2058011A1 (en) * 2007-11-07 2009-05-13 Wittycell Nkt cell activating gycolipids covalently bound antigens and/or drug
BRPI0820960B8 (pt) * 2007-12-05 2021-05-25 Abivax composição, composição farmacêutica, e uso da composição
JP2011524375A (ja) 2008-06-16 2011-09-01 アカデミア シニカ GloboHおよびSSEA3に特異的な免疫反応を誘起する組成物および癌治療におけるその使用
US7928077B2 (en) 2008-07-11 2011-04-19 Academia Sinica Alpha-galactosyl ceramide analogs and their use as immunotherapies
GB2461656B (en) * 2008-07-11 2012-11-21 Academia Sinica Alpha-galactosyl ceramide analogues and their use as immunotherapies, adjuvants, and antiviral, antibacterial and anticancer agents
DK2318832T3 (da) 2008-07-15 2014-01-20 Academia Sinica Glycan-arrays på PTFE-lignende aluminiumcoatede objektglas og relaterede fremgangsmåder
US9220767B2 (en) * 2008-10-08 2015-12-29 Abivax Vaccine composition for use against influenza
KR101928684B1 (ko) * 2009-01-08 2018-12-12 앨버트 아인슈타인 컬리지 오브 메디신, 인크. 세포벽 결합 세라미드 유사 당지질을 갖는 박테리아 백신 및 이의 용도
US10087236B2 (en) 2009-12-02 2018-10-02 Academia Sinica Methods for modifying human antibodies by glycan engineering
US11377485B2 (en) 2009-12-02 2022-07-05 Academia Sinica Methods for modifying human antibodies by glycan engineering
WO2011130332A1 (en) 2010-04-12 2011-10-20 Academia Sinica Glycan arrays for high throughput screening of viruses
JP6057300B2 (ja) 2011-01-05 2017-01-11 ナショナル タイワン ユニバーシティ グリコスフィンゴ脂質の調製及びその使用の方法
US20120288525A1 (en) 2011-05-11 2012-11-15 Chakravarty Sumana Pharmaceutical compositions comprising attenuated plasmodium sporozoites and glycolipid adjuvants
US10130714B2 (en) 2012-04-14 2018-11-20 Academia Sinica Enhanced anti-influenza agents conjugated with anti-inflammatory activity
WO2014017928A1 (en) * 2012-07-26 2014-01-30 Callaghan Innovation Research Limited Organic compounds
US9914956B2 (en) 2012-08-18 2018-03-13 Academia Sinica Cell-permeable probes for identification and imaging of sialidases
JP6548579B2 (ja) * 2012-12-06 2019-07-24 ヴィクトリア リンク リミテッド コンジュゲート化合物
CA2900524A1 (en) 2013-02-08 2014-08-14 Albert Einstein College Of Medicine Of Yeshiva University Modified glycolipids and methods of making and using the same
US9371352B2 (en) 2013-02-08 2016-06-21 Vaccinex, Inc. Modified glycolipids and methods of making and using the same
WO2014210397A1 (en) 2013-06-26 2014-12-31 Academia Sinica Rm2 antigens and use thereof
EP3013347B1 (en) 2013-06-27 2019-12-11 Academia Sinica Glycan conjugates and use thereof
EP3041484B1 (en) * 2013-09-06 2021-03-03 Academia Sinica Human inkt cell activation using glycolipids with altered glycosyl groups
KR20160104727A (ko) 2014-01-16 2016-09-05 아카데미아 시니카 암의 치료 및 검출을 위한 조성물 및 방법
US10150818B2 (en) 2014-01-16 2018-12-11 Academia Sinica Compositions and methods for treatment and detection of cancers
TWI797430B (zh) 2014-03-27 2023-04-01 中央研究院 反應性標記化合物及其用途
US10118969B2 (en) 2014-05-27 2018-11-06 Academia Sinica Compositions and methods relating to universal glycoforms for enhanced antibody efficacy
EP4116329A1 (en) 2014-05-27 2023-01-11 Academia Sinica Anti-her2 glycoantibodies and uses thereof
JP2017518989A (ja) 2014-05-27 2017-07-13 アカデミア シニカAcademia Sinica 抗cd20糖操作抗体群およびその使用
KR20170010003A (ko) 2014-05-27 2017-01-25 아카데미아 시니카 박테로이드 기원의 푸코시다제 및 이의 사용 방법
JP7063538B2 (ja) 2014-05-28 2022-05-09 アカデミア シニカ 抗TNFα糖操作抗体群およびその使用
EP3191500A4 (en) 2014-09-08 2018-04-11 Academia Sinica HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
US9975965B2 (en) 2015-01-16 2018-05-22 Academia Sinica Compositions and methods for treatment and detection of cancers
US10495645B2 (en) 2015-01-16 2019-12-03 Academia Sinica Cancer markers and methods of use thereof
AU2015378564A1 (en) 2015-01-24 2017-07-13 Academia Sinica Novel glycan conjugates and methods of use thereof
CN109195996A (zh) 2016-03-08 2019-01-11 中央研究院 N-聚醣及其阵列的模组化合成方法
CA3034057A1 (en) 2016-08-22 2018-03-01 CHO Pharma Inc. Antibodies, binding fragments, and methods of use
CN106496012B (zh) * 2016-10-08 2019-03-22 张家港市华昌药业有限公司 一种α-羟基十四酸的制备方法
EP4301374A4 (en) 2021-03-01 2025-09-10 Deciduous Therapeutics Inc COMPOUNDS FOR ACTIVATING INVARIANT NATURAL KILLER T CELLS AND METHODS OF USE IN ELIMINATING INFLAMMATORY SENESCENT CELLS

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5936076A (en) * 1991-08-29 1999-08-10 Kirin Beer Kabushiki Kaisha αgalactosylceramide derivatives
AU687733B2 (en) 1992-04-01 1998-03-05 Rockefeller University, The Method for in vitro proliferation of dendritic cell precursors and their use to produce immunogens
TW261533B (cg-RX-API-DMAC10.html) * 1992-07-16 1995-11-01 Kirin Brewery
ATE191916T1 (de) * 1992-10-22 2000-05-15 Kirin Brewery Neues sphingolglycolipid und verwendung davon
US5405772A (en) 1993-06-18 1995-04-11 Amgen Inc. Medium for long-term proliferation and development of cells
AU702871B2 (en) 1993-08-23 1999-03-11 Nexell Therapeutics Inc. (In vitro) growth of neutrophil and megakaryocyte precursors in serum-free media
US5663151A (en) * 1994-03-04 1997-09-02 Bristol-Myers Squibb Company Sulfated α-glycolipid derivatives as cell adhesion inhibitors
US6417167B1 (en) * 1997-02-05 2002-07-09 Kirin Beer Kabushiki Kaisha Lyophilized compositions containing shingoglycolipid and process for preparing them
EP1520583B1 (en) * 1997-04-10 2009-01-28 Kyowa Hakko Kirin Co., Ltd. NKT cell-activating agents containing alpha-glycosylceramides
AU2002327097B2 (en) * 2001-08-16 2007-05-24 Japan As Represented By President Of National Centre Of Neurology And Psychiatry Novel glycolipid and remedial agent for autoimmune disease containing the same as active ingredient
ES2450043T3 (es) * 2003-02-14 2014-03-21 Japan As Represented By President Of National Center Of Neurology And Psychiatry Ministry Of Healt Derivados del glicolípido, proceso para su producción, intermedios para la síntesis del mismo, y proceso para la producción de los intermedios
AU2005280163B2 (en) * 2004-08-27 2011-11-24 Albert Einstein College Of Medicine, Inc. Ceramide derivatives as modulators of immunity and autoimmunity
JP5090928B2 (ja) 2004-12-28 2012-12-05 ザ ロックフェラー ユニバーシティ Nkt細胞に対する抗原としての糖脂質及びその類似体
US7923013B2 (en) * 2004-12-28 2011-04-12 The Rockefeller University Glycolipids and analogues thereof as antigens for NKT cells
WO2007035717A2 (en) 2005-09-19 2007-03-29 The Rockefeller University Glycolipids and analogues thereof as antigents for nk t cells

Also Published As

Publication number Publication date
WO2006071848A9 (en) 2006-08-17
AU2005322027A1 (en) 2006-07-06
WO2006071848A2 (en) 2006-07-06
US20060211856A1 (en) 2006-09-21
CA2591232A1 (en) 2006-07-06
WO2006071848A3 (en) 2006-09-14
EP1833489A4 (en) 2011-08-03
AU2005322027B2 (en) 2013-09-12
JP2008525495A (ja) 2008-07-17
US20090233875A1 (en) 2009-09-17
US7534434B2 (en) 2009-05-19
EP1833489A2 (en) 2007-09-19
JP5090928B2 (ja) 2012-12-05

Similar Documents

Publication Publication Date Title
AU2005322027B2 (en) Glycolipids and analogues thereof as antigens for NK Tcells
US7923013B2 (en) Glycolipids and analogues thereof as antigens for NKT cells
JP5014573B2 (ja) 脂質aおよび他の炭水化物リガンド類似体
CA2577009C (en) Ceramide derivatives as modulators of immunity and autoimmunity
US20060116331A1 (en) Glycosylceramide analogues
Lee et al. Novel synthesis of α-galactosyl-ceramides and confirmation of their powerful NKT cell agonist activity
Raju et al. Synthesis and evaluation of 3 ″-and 4 ″-deoxy and-fluoro analogs of the immunostimulatory glycolipid, KRN7000
JPWO1998029534A1 (ja) ヒト抗原提示細胞の活性化法、活性化されたヒト抗原提示細胞およびその使用
KR20150127030A (ko) 접합체 화합물
KR102167438B1 (ko) 변형된 당지질들 및 이들을 제조하고 사용하는 방법들
Veerapen et al. Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→ 2) galactosyl ceramide
Hung et al. Design and synthesis of galactose-6-OH-modified α-galactosyl ceramide analogues with Th2-biased immune responses
Thomann et al. Novel glycolipid TLR2 ligands of the type Pam2Cys-α-Gal: Synthesis and biological properties
Pauwels et al. Divergent synthetic approach to 6′′-modified α-GalCer analogues
Park et al. Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry
Li et al. Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
WO2007035717A2 (en) Glycolipids and analogues thereof as antigents for nk t cells
Sadraei Progress towards the Synthesis of Carbohydrate-Based Biomedical and Material-Science Relevant Molecules
Mathew Synthesis of dual adjuvanted peptide vaccines for cancer immunotherapy
Wu The design and synthesis of glycolipids for CD1d-mediated natural killer T-cell activation
Lewicky Novel toll-like receptor 4 ligands: synthesis, biological studies and applications in molecular vaccines
Quaid Synthesis of novel chemical adjuvants for the modulation and study of CD1-d mediated immunological processes
Anderson Synthesis and Immunological Evaluation of Type I, Type II, and γδ NKT Cell Antigens
Chen Design, Synthesis and Immunological Evaluation of Glycoceramides and Glycoproteins for Cancer Immunotherapy & Structure Activity Relationship Study of Daunorubicin Analogues with Uncommon Sugars
Goff Structure-activity studies of glycosphingolipids as antigens of natural killer T cells

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20210831

MKLA Lapsed

Effective date: 20191227