158021-47-7,MFCD00939559
Catalog No.:AA00AE4R

158021-47-7 | KRN7000

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥96%
in stock  
$362.00   $253.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00AE4R
Chemical Name:
KRN7000
CAS Number:
158021-47-7
Molecular Formula:
C50H99NO9
Molecular Weight:
858.3224
MDL Number:
MFCD00939559
SMILES:
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)CO[C@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
Properties
Computed Properties
 
Complexity:
928  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
60  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0  
Rotatable Bond Count:
44  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
16  

Literature

Title: Chronic alcohol consumption enhances iNKT cell maturation and activation.

Journal: Toxicology and applied pharmacology 20150115

Title: Enhanced TCR footprint by a novel glycolipid increases NKT-dependent tumor protection.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20130915

Title: Bacterial CD1d-restricted glycolipids induce IL-10 production by human regulatory T cells upon cross-talk with invariant NKT cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20130901

Title: Slam haplotype 2 promotes NKT but suppresses Vγ4+ T-cell activation in coxsackievirus B3 infection leading to increased liver damage but reduced myocarditis.

Journal: The American journal of pathology 20130201

Title: Recognition of microbial and mammalian phospholipid antigens by NKT cells with diverse TCRs.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20130129

Title: Lack of PD-L1 expression by iNKT cells improves the course of influenza A infection.

Journal: PloS one 20130101

Title: CD1d-dependent, iNKT-cell cytotoxicity against keratinocytes in allergic contact dermatitis.

Journal: Experimental dermatology 20121201

Title: Human and mouse type I natural killer T cell antigen receptors exhibit different fine specificities for CD1d-antigen complex.

Journal: The Journal of biological chemistry 20121109

Title: The molecular basis for recognition of CD1d/α-galactosylceramide by a human non-Vα24 T cell receptor.

Journal: PLoS biology 20121001

Title: Key role for respiratory CD103(+) dendritic cells, IFN-γ, and IL-17 in protection against Streptococcus pneumoniae infection in response to α-galactosylceramide.

Journal: The Journal of infectious diseases 20120901

Title: Type II natural killer T cells use features of both innate-like and conventional T cells to recognize sulfatide self antigens.

Journal: Nature immunology 20120901

Title: C-Glycosphingolipids with an exo-methylene substituent: stereocontrolled synthesis and immunostimulation of mouse and human natural killer T lymphocytes.

Journal: Chembiochem : a European journal of chemical biology 20120813

Title: RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines.

Journal: Bioorganic & medicinal chemistry 20120715

Title: Activation of invariant natural killer T cells by lipid excess promotes tissue inflammation, insulin resistance, and hepatic steatosis in obese mice.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20120508

Title: Bacterial species-characteristic profiles of molecular species, and the antigenicity of phospholipids and glycolipids in symbiotic Lactobacillus, Staphylococcus and Streptococcus species.

Journal: Glycoconjugate journal 20120501

Title: Lysophospholipid presentation by CD1d and recognition by a human Natural Killer T-cell receptor.

Journal: The EMBO journal 20120418

Title: Structural and functional characterization of a novel nonglycosidic type I NKT agonist with immunomodulatory properties.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120301

Title: 3-fluoro- and 3,3-difluoro-3,4-dideoxy-KRN7000 analogues as new potent immunostimulator agents: total synthesis and biological evaluation in human invariant natural killer T cells and mice.

Journal: Journal of medicinal chemistry 20120209

Title: Structural basis for the recognition of C20:2-αGalCer by the invariant natural killer T cell receptor-like antibody L363.

Journal: The Journal of biological chemistry 20120106

Title: Natural variations at position 93 of the invariant Vα24-Jα18 α chain of human iNKT-cell TCRs strongly impact on CD1d binding.

Journal: European journal of immunology 20120101

Title: Crystal structures of bovine CD1d reveal altered αGalCer presentation and a restricted A' pocket unable to bind long-chain glycolipids.

Journal: PloS one 20120101

Title: Activation of Invariant NKT cells with glycolipid ligand α-galactosylceramide ameliorates glucose-6-phosphate isomerase peptide-induced arthritis.

Journal: PloS one 20120101

Title: Divergent synthetic approach to 6''-modified α-GalCer analogues.

Journal: Organic & biomolecular chemistry 20111221

Title: Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Journal: The Journal of organic chemistry 20111104

Title: Invariant NKT cell defects in vitamin D receptor knockout mice prevents experimental lung inflammation.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20111101

Title: Prevention of type 1 diabetes by inducing subclinical dermatitis on a small area.

Journal: Diabetes/metabolism research and reviews 20111101

Title: Unique interplay between sugar and lipid in determining the antigenic potency of bacterial antigens for NKT cells.

Journal: PLoS biology 20111101

Title: Invariant natural killer T cells recognize glycolipids from pathogenic Gram-positive bacteria.

Journal: Nature immunology 20111001

Title: Cutting edge: structural basis for the recognition of β-linked glycolipid antigens by invariant NKT cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20110901

Title: Recognition of β-linked self glycolipids mediated by natural killer T cell antigen receptors.

Journal: Nature immunology 20110731

Title: A semi-invariant Vα10+ T cell antigen receptor defines a population of natural killer T cells with distinct glycolipid antigen-recognition properties.

Journal: Nature immunology 20110612

Title: Innate and cytokine-driven signals, rather than microbial antigens, dominate in natural killer T cell activation during microbial infection.

Journal: The Journal of experimental medicine 20110606

Title: Galactose-modified iNKT cell agonists stabilized by an induced fit of CD1d prevent tumour metastasis.

Journal: The EMBO journal 20110601

Title: Functional invariant NKT cells in pig lungs regulate the airway hyperreactivity: a potential animal model.

Journal: Journal of clinical immunology 20110401

Title: A molecular basis for the exquisite CD1d-restricted antigen specificity and functional responses of natural killer T cells.

Journal: Immunity 20110325

Title: A molecular basis for NKT cell recognition of CD1d-self-antigen.

Journal: Immunity 20110325

Title: Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.

Journal: The Journal of organic chemistry 20110107

Title: Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation.

Journal: Bioorganic & medicinal chemistry 20110101

Title: Development of spontaneous anergy in invariant natural killer T cells in a mouse model of dyslipidemia.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20100901

Title: Synthesis and biological activity of ester and ether analogues of alpha-galactosylceramide (KRN7000).

Journal: Carbohydrate research 20100816

Title: Invariant NKT cells are required for antitumor responses induced by host-versus-graft responses.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100815

Title: Dietary fatty acids modulate antigen presentation to hepatic NKT cells in nonalcoholic fatty liver disease.

Journal: Journal of lipid research 20100701

Title: Plasticity of invariant NKT cell regulation of allergic airway disease is dependent on IFN-gamma production.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100701

Title: Slam haplotypes modulate the response to lipopolysaccharide in vivo through control of NKT cell number and function.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100701

Title: Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000.

Journal: Bioorganic & medicinal chemistry letters 20100601

Title: Fatty acid amide hydrolase shapes NKT cell responses by influencing the serum transport of lipid antigen in mice.

Journal: The Journal of clinical investigation 20100601

Title: Innate-like control of human iNKT cell autoreactivity via the hypervariable CDR3beta loop.

Journal: PLoS biology 20100601

Title: CD1d-dependent B-cell help by NK-like T cells leads to enhanced and sustained production of Bacillus anthracis lethal toxin-neutralizing antibodies.

Journal: Infection and immunity 20100401

Title: A CD1d-dependent antagonist inhibits the activation of invariant NKT cells and prevents development of allergen-induced airway hyperreactivity.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100215

Title: Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

Journal: Bioorganic & medicinal chemistry letters 20100201

Title: Lipid binding orientation within CD1d affects recognition of Borrelia burgorferi antigens by NKT cells.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20100126

Title: PD-L1 and PD-L2 modulate airway inflammation and iNKT-cell-dependent airway hyperreactivity in opposing directions.

Journal: Mucosal immunology 20100101

Title: Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100101

Title: Bacillus anthracis lethal toxin disrupts TCR signaling in CD1d-restricted NKT cells leading to functional anergy.

Journal: PLoS pathogens 20090901

Title: Focus on the controversial activation of human iNKT cells by 4-deoxy analogue of KRN7000.

Journal: Journal of medicinal chemistry 20090813

Title: Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.

Journal: Bioorganic & medicinal chemistry letters 20090801

Title: Skin and peripheral lymph node invariant NKT cells are mainly retinoic acid receptor-related orphan receptor (gamma)t+ and respond preferentially under inflammatory conditions.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20090801

Title: Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors.

Journal: Immunity 20090717

Title: Cutting edge: B and T lymphocyte attenuator signaling on NKT cells inhibits cytokine release and tissue injury in early immune responses.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20090701

Title: Induction of airway hyperreactivity by IL-25 is dependent on a subset of invariant NKT cells expressing IL-17RB.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20090415

Title: Alpha-S-GalCer: synthesis and evaluation for iNKT cell stimulation.

Journal: Bioorganic & medicinal chemistry letters 20081215

Title: Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment.

Journal: The Journal of organic chemistry 20081121

Title: Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000.

Journal: Organic letters 20081016

Title: The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000.

Journal: Organic letters 20081016

Title: RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.

Journal: Bioorganic & medicinal chemistry 20081001

Title: Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH.

Journal: Transplantation 20080815

Title: Alpha-lactosylceramide as a novel 'sugar-capped' CD1d ligand for natural killer T cells: biased cytokine profile and therapeutic activities.

Journal: Chembiochem : a European journal of chemical biology 20080616

Title: Glycolipid-activated NKT cells support the induction of persistent plasma cell responses and antibody titers.

Journal: European journal of immunology 20080401

Title: RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines.

Journal: Bioorganic & medicinal chemistry 20080115

Title: Immunization with dendritic cells loaded with alpha-galactosylceramide at priming phase, but not at boosting phase, enhances cytotoxic T lymphocyte activity against infection by intracellular bacteria.

Journal: FEMS immunology and medical microbiology 20071101

Title: iNKT cells require CCR4 to localize to the airways and to induce airway hyperreactivity.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20071001

Title: A general and stereoselective route to alpha- or beta-galactosphingolipids via a common four-carbon building block.

Journal: The Journal of organic chemistry 20070928

Title: A Y chromosome-linked factor impairs NK T development.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20070915

Title: CD1d-lipid-antigen recognition by the semi-invariant NKT T-cell receptor.

Journal: Nature 20070705

Title: Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.

Journal: Bioorganic & medicinal chemistry letters 20070515

Title: Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer.

Journal: Journal of medicinal chemistry 20070208

Title: During acute Trypanosoma cruzi infection highly susceptible mice deficient in natural killer cells are protected by a single alpha-galactosylceramide treatment.

Journal: Immunology 20061101

Title: The CD1d-binding glycolipid alpha-galactosylceramide enhances humoral immunity to T-dependent and T-independent antigen in a CD1d-dependent manner.

Journal: Immunology 20060901

Title: Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3).

Journal: Bioorganic & medicinal chemistry letters 20060415

Title: Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20060314

Title: Chemoenzymatic syntheses of iGb3 and Gb3.

Journal: Organic letters 20060302

Title: Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH.

Journal: The Journal of organic chemistry 20051209

Title: NK T cell activation promotes Chlamydia trachomatis infection in vivo.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20050901

Title: The crystal structure of human CD1d with and without alpha-galactosylceramide.

Journal: Nature immunology 20050801

Title: Structure and function of a potent agonist for the semi-invariant natural killer T cell receptor.

Journal: Nature immunology 20050801

Title: Sustained expansion of NKT cells and antigen-specific T cells after injection of alpha-galactosyl-ceramide loaded mature dendritic cells in cancer patients.

Journal: The Journal of experimental medicine 20050502

Title: Quantitative and qualitative differences in the in vivo response of NKT cells to distinct alpha- and beta-anomeric glycolipids.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20040915

Title: Enhancement of the synthetic ligand-mediated function of liver NK1.1Ag+ T cells in mice by interleukin-12 pretreatment.

Journal: Immunology 20040901

Title: Human NKT cells express granulysin and exhibit antimycobacterial activity.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030315

Title: Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY alpha-galactosylceramide.

Journal: Chembiochem : a European journal of chemical biology 20030103

Title: No inhibition of urinary bladder carcinogenesis in rats with intravesical instillation of alpha-galactosylceramide.

Journal: Asian Pacific journal of cancer prevention : APJCP 20030101

Title: Disruption of T helper 2-immune responses in Epstein-Barr virus-induced gene 3-deficient mice.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20021224

Title: Enhancing effects of (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-2-(N-hexacosanoylamino) -1,3,4-octadecanetriol (KRN7000) on antigen-presenting function of antigen-presenting cells and antimetastatic activity of KRN7000-pretreated antigen-presenting cells.

Journal: Oncology research 19960101

Title: Characterization of neutral glycosphingolipids in rat lens.

Journal: Experimental eye research 19950201

Title: KRN7000, a novel immunomodulator, and its antitumor activities.

Journal: Oncology research 19950101

Title: Godfrey DI, et al. Going both ways: immune regulation via CD1d-dependent NKT cells. J Clin Invest. 2004 Nov;114(10):1379-88.

Title: Morita M, et al. Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylcer-amide, KRN7000. Biosci Biotechnol Biochem. 1996 Jan;60(2):288-92.

Title: Kikuchi A, et al. In vitro anti-tumour activity of alpha-galactosylceramide-stimulated human invariant Valpha24+NKT cells against melanoma. Br J Cancer. 2001 Sep 1;85(5):741-6.

Title: Masahiro Morita, et al. Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice. J. Med. Chem. 1995, 38, 12, 2176-2187.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:158021-47-7 Molecular Formula|158021-47-7 MDL|158021-47-7 SMILES|158021-47-7 KRN7000
Catalog No.: AA00AE4R
158021-47-7,MFCD00939559
158021-47-7 | KRN7000
Pack Size: 1mg
Purity: ≥96%
in stock
$362.00 $253.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA00AE4R
Chemical Name: KRN7000
CAS Number: 158021-47-7
Molecular Formula: C50H99NO9
Molecular Weight: 858.3224
MDL Number: MFCD00939559
SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)CO[C@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
Properties
Complexity: 928  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 8  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 60  
Hydrogen Bond Acceptor Count: 9  
Hydrogen Bond Donor Count: 7  
Isotope Atom Count: 0  
Rotatable Bond Count: 44  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 16  
Literature fold

Title: Chronic alcohol consumption enhances iNKT cell maturation and activation.

Journal: Toxicology and applied pharmacology20150115

Title: Enhanced TCR footprint by a novel glycolipid increases NKT-dependent tumor protection.

Journal: Journal of immunology (Baltimore, Md. : 1950)20130915

Title: Bacterial CD1d-restricted glycolipids induce IL-10 production by human regulatory T cells upon cross-talk with invariant NKT cells.

Journal: Journal of immunology (Baltimore, Md. : 1950)20130901

Title: Slam haplotype 2 promotes NKT but suppresses Vγ4+ T-cell activation in coxsackievirus B3 infection leading to increased liver damage but reduced myocarditis.

Journal: The American journal of pathology20130201

Title: Recognition of microbial and mammalian phospholipid antigens by NKT cells with diverse TCRs.

Journal: Proceedings of the National Academy of Sciences of the United States of America20130129

Title: Lack of PD-L1 expression by iNKT cells improves the course of influenza A infection.

Journal: PloS one20130101

Title: CD1d-dependent, iNKT-cell cytotoxicity against keratinocytes in allergic contact dermatitis.

Journal: Experimental dermatology20121201

Title: Human and mouse type I natural killer T cell antigen receptors exhibit different fine specificities for CD1d-antigen complex.

Journal: The Journal of biological chemistry20121109

Title: The molecular basis for recognition of CD1d/α-galactosylceramide by a human non-Vα24 T cell receptor.

Journal: PLoS biology20121001

Title: Key role for respiratory CD103(+) dendritic cells, IFN-γ, and IL-17 in protection against Streptococcus pneumoniae infection in response to α-galactosylceramide.

Journal: The Journal of infectious diseases20120901

Title: Type II natural killer T cells use features of both innate-like and conventional T cells to recognize sulfatide self antigens.

Journal: Nature immunology20120901

Title: C-Glycosphingolipids with an exo-methylene substituent: stereocontrolled synthesis and immunostimulation of mouse and human natural killer T lymphocytes.

Journal: Chembiochem : a European journal of chemical biology20120813

Title: RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines.

Journal: Bioorganic & medicinal chemistry20120715

Title: Activation of invariant natural killer T cells by lipid excess promotes tissue inflammation, insulin resistance, and hepatic steatosis in obese mice.

Journal: Proceedings of the National Academy of Sciences of the United States of America20120508

Title: Bacterial species-characteristic profiles of molecular species, and the antigenicity of phospholipids and glycolipids in symbiotic Lactobacillus, Staphylococcus and Streptococcus species.

Journal: Glycoconjugate journal20120501

Title: Lysophospholipid presentation by CD1d and recognition by a human Natural Killer T-cell receptor.

Journal: The EMBO journal20120418

Title: Structural and functional characterization of a novel nonglycosidic type I NKT agonist with immunomodulatory properties.

Journal: Journal of immunology (Baltimore, Md. : 1950)20120301

Title: 3-fluoro- and 3,3-difluoro-3,4-dideoxy-KRN7000 analogues as new potent immunostimulator agents: total synthesis and biological evaluation in human invariant natural killer T cells and mice.

Journal: Journal of medicinal chemistry20120209

Title: Structural basis for the recognition of C20:2-αGalCer by the invariant natural killer T cell receptor-like antibody L363.

Journal: The Journal of biological chemistry20120106

Title: Natural variations at position 93 of the invariant Vα24-Jα18 α chain of human iNKT-cell TCRs strongly impact on CD1d binding.

Journal: European journal of immunology20120101

Title: Crystal structures of bovine CD1d reveal altered αGalCer presentation and a restricted A' pocket unable to bind long-chain glycolipids.

Journal: PloS one20120101

Title: Activation of Invariant NKT cells with glycolipid ligand α-galactosylceramide ameliorates glucose-6-phosphate isomerase peptide-induced arthritis.

Journal: PloS one20120101

Title: Divergent synthetic approach to 6''-modified α-GalCer analogues.

Journal: Organic & biomolecular chemistry20111221

Title: Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Journal: The Journal of organic chemistry20111104

Title: Invariant NKT cell defects in vitamin D receptor knockout mice prevents experimental lung inflammation.

Journal: Journal of immunology (Baltimore, Md. : 1950)20111101

Title: Prevention of type 1 diabetes by inducing subclinical dermatitis on a small area.

Journal: Diabetes/metabolism research and reviews20111101

Title: Unique interplay between sugar and lipid in determining the antigenic potency of bacterial antigens for NKT cells.

Journal: PLoS biology20111101

Title: Invariant natural killer T cells recognize glycolipids from pathogenic Gram-positive bacteria.

Journal: Nature immunology20111001

Title: Cutting edge: structural basis for the recognition of β-linked glycolipid antigens by invariant NKT cells.

Journal: Journal of immunology (Baltimore, Md. : 1950)20110901

Title: Recognition of β-linked self glycolipids mediated by natural killer T cell antigen receptors.

Journal: Nature immunology20110731

Title: A semi-invariant Vα10+ T cell antigen receptor defines a population of natural killer T cells with distinct glycolipid antigen-recognition properties.

Journal: Nature immunology20110612

Title: Innate and cytokine-driven signals, rather than microbial antigens, dominate in natural killer T cell activation during microbial infection.

Journal: The Journal of experimental medicine20110606

Title: Galactose-modified iNKT cell agonists stabilized by an induced fit of CD1d prevent tumour metastasis.

Journal: The EMBO journal20110601

Title: Functional invariant NKT cells in pig lungs regulate the airway hyperreactivity: a potential animal model.

Journal: Journal of clinical immunology20110401

Title: A molecular basis for the exquisite CD1d-restricted antigen specificity and functional responses of natural killer T cells.

Journal: Immunity20110325

Title: A molecular basis for NKT cell recognition of CD1d-self-antigen.

Journal: Immunity20110325

Title: Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.

Journal: The Journal of organic chemistry20110107

Title: Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation.

Journal: Bioorganic & medicinal chemistry20110101

Title: Development of spontaneous anergy in invariant natural killer T cells in a mouse model of dyslipidemia.

Journal: Arteriosclerosis, thrombosis, and vascular biology20100901

Title: Synthesis and biological activity of ester and ether analogues of alpha-galactosylceramide (KRN7000).

Journal: Carbohydrate research20100816

Title: Invariant NKT cells are required for antitumor responses induced by host-versus-graft responses.

Journal: Journal of immunology (Baltimore, Md. : 1950)20100815

Title: Dietary fatty acids modulate antigen presentation to hepatic NKT cells in nonalcoholic fatty liver disease.

Journal: Journal of lipid research20100701

Title: Plasticity of invariant NKT cell regulation of allergic airway disease is dependent on IFN-gamma production.

Journal: Journal of immunology (Baltimore, Md. : 1950)20100701

Title: Slam haplotypes modulate the response to lipopolysaccharide in vivo through control of NKT cell number and function.

Journal: Journal of immunology (Baltimore, Md. : 1950)20100701

Title: Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000.

Journal: Bioorganic & medicinal chemistry letters20100601

Title: Fatty acid amide hydrolase shapes NKT cell responses by influencing the serum transport of lipid antigen in mice.

Journal: The Journal of clinical investigation20100601

Title: Innate-like control of human iNKT cell autoreactivity via the hypervariable CDR3beta loop.

Journal: PLoS biology20100601

Title: CD1d-dependent B-cell help by NK-like T cells leads to enhanced and sustained production of Bacillus anthracis lethal toxin-neutralizing antibodies.

Journal: Infection and immunity20100401

Title: A CD1d-dependent antagonist inhibits the activation of invariant NKT cells and prevents development of allergen-induced airway hyperreactivity.

Journal: Journal of immunology (Baltimore, Md. : 1950)20100215

Title: Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

Journal: Bioorganic & medicinal chemistry letters20100201

Title: Lipid binding orientation within CD1d affects recognition of Borrelia burgorferi antigens by NKT cells.

Journal: Proceedings of the National Academy of Sciences of the United States of America20100126

Title: PD-L1 and PD-L2 modulate airway inflammation and iNKT-cell-dependent airway hyperreactivity in opposing directions.

Journal: Mucosal immunology20100101

Title: Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells.

Journal: Journal of immunology (Baltimore, Md. : 1950)20100101

Title: Bacillus anthracis lethal toxin disrupts TCR signaling in CD1d-restricted NKT cells leading to functional anergy.

Journal: PLoS pathogens20090901

Title: Focus on the controversial activation of human iNKT cells by 4-deoxy analogue of KRN7000.

Journal: Journal of medicinal chemistry20090813

Title: Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.

Journal: Bioorganic & medicinal chemistry letters20090801

Title: Skin and peripheral lymph node invariant NKT cells are mainly retinoic acid receptor-related orphan receptor (gamma)t+ and respond preferentially under inflammatory conditions.

Journal: Journal of immunology (Baltimore, Md. : 1950)20090801

Title: Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors.

Journal: Immunity20090717

Title: Cutting edge: B and T lymphocyte attenuator signaling on NKT cells inhibits cytokine release and tissue injury in early immune responses.

Journal: Journal of immunology (Baltimore, Md. : 1950)20090701

Title: Induction of airway hyperreactivity by IL-25 is dependent on a subset of invariant NKT cells expressing IL-17RB.

Journal: Journal of immunology (Baltimore, Md. : 1950)20090415

Title: Alpha-S-GalCer: synthesis and evaluation for iNKT cell stimulation.

Journal: Bioorganic & medicinal chemistry letters20081215

Title: Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment.

Journal: The Journal of organic chemistry20081121

Title: Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000.

Journal: Organic letters20081016

Title: The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000.

Journal: Organic letters20081016

Title: RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.

Journal: Bioorganic & medicinal chemistry20081001

Title: Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH.

Journal: Transplantation20080815

Title: Alpha-lactosylceramide as a novel 'sugar-capped' CD1d ligand for natural killer T cells: biased cytokine profile and therapeutic activities.

Journal: Chembiochem : a European journal of chemical biology20080616

Title: Glycolipid-activated NKT cells support the induction of persistent plasma cell responses and antibody titers.

Journal: European journal of immunology20080401

Title: RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines.

Journal: Bioorganic & medicinal chemistry20080115

Title: Immunization with dendritic cells loaded with alpha-galactosylceramide at priming phase, but not at boosting phase, enhances cytotoxic T lymphocyte activity against infection by intracellular bacteria.

Journal: FEMS immunology and medical microbiology20071101

Title: iNKT cells require CCR4 to localize to the airways and to induce airway hyperreactivity.

Journal: Journal of immunology (Baltimore, Md. : 1950)20071001

Title: A general and stereoselective route to alpha- or beta-galactosphingolipids via a common four-carbon building block.

Journal: The Journal of organic chemistry20070928

Title: A Y chromosome-linked factor impairs NK T development.

Journal: Journal of immunology (Baltimore, Md. : 1950)20070915

Title: CD1d-lipid-antigen recognition by the semi-invariant NKT T-cell receptor.

Journal: Nature20070705

Title: Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.

Journal: Bioorganic & medicinal chemistry letters20070515

Title: Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer.

Journal: Journal of medicinal chemistry20070208

Title: During acute Trypanosoma cruzi infection highly susceptible mice deficient in natural killer cells are protected by a single alpha-galactosylceramide treatment.

Journal: Immunology20061101

Title: The CD1d-binding glycolipid alpha-galactosylceramide enhances humoral immunity to T-dependent and T-independent antigen in a CD1d-dependent manner.

Journal: Immunology20060901

Title: Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3).

Journal: Bioorganic & medicinal chemistry letters20060415

Title: Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d.

Journal: Proceedings of the National Academy of Sciences of the United States of America20060314

Title: Chemoenzymatic syntheses of iGb3 and Gb3.

Journal: Organic letters20060302

Title: Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH.

Journal: The Journal of organic chemistry20051209

Title: NK T cell activation promotes Chlamydia trachomatis infection in vivo.

Journal: Journal of immunology (Baltimore, Md. : 1950)20050901

Title: The crystal structure of human CD1d with and without alpha-galactosylceramide.

Journal: Nature immunology20050801

Title: Structure and function of a potent agonist for the semi-invariant natural killer T cell receptor.

Journal: Nature immunology20050801

Title: Sustained expansion of NKT cells and antigen-specific T cells after injection of alpha-galactosyl-ceramide loaded mature dendritic cells in cancer patients.

Journal: The Journal of experimental medicine20050502

Title: Quantitative and qualitative differences in the in vivo response of NKT cells to distinct alpha- and beta-anomeric glycolipids.

Journal: Journal of immunology (Baltimore, Md. : 1950)20040915

Title: Enhancement of the synthetic ligand-mediated function of liver NK1.1Ag+ T cells in mice by interleukin-12 pretreatment.

Journal: Immunology20040901

Title: Human NKT cells express granulysin and exhibit antimycobacterial activity.

Journal: Journal of immunology (Baltimore, Md. : 1950)20030315

Title: Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY alpha-galactosylceramide.

Journal: Chembiochem : a European journal of chemical biology20030103

Title: No inhibition of urinary bladder carcinogenesis in rats with intravesical instillation of alpha-galactosylceramide.

Journal: Asian Pacific journal of cancer prevention : APJCP20030101

Title: Disruption of T helper 2-immune responses in Epstein-Barr virus-induced gene 3-deficient mice.

Journal: Proceedings of the National Academy of Sciences of the United States of America20021224

Title: Enhancing effects of (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-2-(N-hexacosanoylamino) -1,3,4-octadecanetriol (KRN7000) on antigen-presenting function of antigen-presenting cells and antimetastatic activity of KRN7000-pretreated antigen-presenting cells.

Journal: Oncology research19960101

Title: Characterization of neutral glycosphingolipids in rat lens.

Journal: Experimental eye research19950201

Title: KRN7000, a novel immunomodulator, and its antitumor activities.

Journal: Oncology research19950101

Title: Godfrey DI, et al. Going both ways: immune regulation via CD1d-dependent NKT cells. J Clin Invest. 2004 Nov;114(10):1379-88.

Title: Morita M, et al. Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylcer-amide, KRN7000. Biosci Biotechnol Biochem. 1996 Jan;60(2):288-92.

Title: Kikuchi A, et al. In vitro anti-tumour activity of alpha-galactosylceramide-stimulated human invariant Valpha24+NKT cells against melanoma. Br J Cancer. 2001 Sep 1;85(5):741-6.

Title: Masahiro Morita, et al. Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice. J. Med. Chem. 1995, 38, 12, 2176-2187.

Building Blocks More >
121905-03-1
121905-03-1
4-Formyl-1-methyl-1H-pyrazole-5-sulfonamide
AA00AHNF | MFCD18809746
17199-34-7
17199-34-7
1-(3,5-Dichlorophenoxy)propan-2-one
AA00AK3V | MFCD11100440
1560797-76-3
1560797-76-3
N,N,N',N'-TETRAAMYLMALONAMIDE
AA00AKJH | MFCD06797172
143707-72-6
143707-72-6
tert-Butyl 3-(methylamino)propanoate
AA00AKR8 | MFCD08275841
193290-27-6
193290-27-6
3-(2-Hydroxyethyl)benzonitrile
AA00ALX2 | MFCD10001394
1630193-77-9
1630193-77-9
(2,5-dimethoxypyridin-4-yl)boronic acid
AA00AMDK | MFCD18256800
148502-20-9
148502-20-9
7-Amino-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one hydrochloride
AA00AMPC | MFCD04035629
188612-53-5
188612-53-5
5-(Amino-1-(N-methyl Carbamoyl)
AA00ANCZ | MFCD20691204
145724-15-8
145724-15-8
tert-Butyl (4,4-dimethylpyrrolidin-3-yl)carbamate
AA00ANL9 | MFCD24368654
168835-82-3
168835-82-3
Su1498
AA00AO01 | MFCD03453026
Submit
© 2017 AA BLOCKS, INC. All rights reserved.