CAS 109944-15-2|Kifunensine
| Common Name | Kifunensine | ||
|---|---|---|---|
| CAS Number | 109944-15-2 | Molecular Weight | 232.191 |
| Density | 1.9±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C8H12N2O6 | Melting Point | >280℃ |
| MSDS | ChineseUSA | Flash Point | / |
Names
| Name | Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione |
|---|---|
| Synonym | More Synonyms |
Kifunensine BiologicalActivity
| Description | Kifunensine, a potent and selective inhibitor of class I α-mannosidases isolated from Actinomycete, prevents α-mannosidases I from trimming mannose residues on glycoproteins. Kifunensine inhibits ERAD[1][2][3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology |
| In Vitro | Kifunensine, an alkaloid from actinomycete Kitasatosporia kifunense 9482, is the most efficient nhibitor of a-mannosidase I, blocking N-glycan synthesis at an8GlcNAc2 (Man8) or Man9GlcNAc2 (Man9) stage[3]. RT-PCR[3]. Cell Line: Hybridoma cells expressing a human IgG1 monoclonal Antibody[3]. Concentration: 2 μg/mL. Incubation Time: 4 days. Result: Significantly reduced the lentil lectin binding. Kifunensine is the most effective among the inhibitors tested in producing antibodies containing oligomannose residues without fucose. |
| In Vivo | Animal Model: BALB/c mice[3]. Dosage: 5 mg/kg. Administration: IV via tail vein. Result: There was no significant difference in the serum levels of anti-TEM B mAb generated from cells treated with or without kifunensine in the 7-day period. |
| References | [1]. Yongao Xiong, et al. Glycoform Modification of Secreted Recombinant Glycoproteins through Kifunensine Addition during Transient Vacuum Agroinfiltration. Int J Mol Sci. 2018 Mar; 19(3): 890. [2]. Hiroshi Kayakiri, et al. Structure of Kifunensine, a New Immunomodulator Isolated from an Actinomycete. J. Org. Chem. 1989,54,4015-4016. [3]. Qun Zhou, et al. Development of a Simple and Rapid Method for Producing Non-Fucosylated Oligomannose Containing Antibodies With Increased Effector Function. Biotechnol Bioeng. 2008 Feb 15;99(3):652-65. [4]. Hyung Lim Elfrink, et al. Inhibition of Endoplasmic Reticulum Associated Degradation Reduces Endoplasmic Reticulum Stress and Alters Lysosomal Morphology and Distribution. Mol Cells. 2013 Apr 30; 35(4): 291–297. |
Chemical & Physical Properties
| Density | 1.9±0.1 g/cm3 |
|---|---|
| Melting Point | >280℃ |
| Molecular Formula | C8H12N2O6 |
| Molecular Weight | 232.191 |
| Exact Mass | 232.069534 |
| PSA | 130.33000 |
| LogP | -2.21 |
| Index of Refraction | 1.706 |
| InChIKey | OIURYJWYVIAOCW-PQMKYFCFSA-N |
| SMILES | O=C1NC2C(O)C(O)C(O)C(CO)N2C1=O |
| Storage condition | -20°C |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Hazard Codes | Xi |
| RIDADR | NONH for all modes of transport |
Articles32
More Articles| A context-independent N-glycan signal targets the misfolded extracellular domain of Arabidopsis STRUBBELIG to endoplasmic-reticulum-associated degradation. Biochem. J. 464(3) , 401-11, (2014) N-glycosylation of proteins plays an important role in the determination of the fate of newly synthesized glycoproteins in the endoplasmic reticulum (ER). Specific oligosaccharide structures recruit m... | |
| Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase. Carbohydr. Res. 365 , 1-8, (2013) An efficient and practical synthesis of kifunensine thioanalogs 1a-c was reported. The bicyclic azasugars fused thiazolidin-4-one 4a-c as key intermediates were first synthesized in good yields of 74-... | |
| Evolution of cross-neutralizing antibody specificities to the CD4-BS and the carbohydrate cloak of the HIV Env in an HIV-1-infected subject. PLoS ONE 7(11) , e49610, (2012) Broadly neutralizing antibodies are considered an important part of a successful HIV vaccine. A better understanding of the factors underlying their development during infection and of the epitopes th... |
Synonyms
| (5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione |
| Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)- |
| KIFUNENSINE,KITASATOSPORIA KIFUNENSE |
| 1-deoxymannojirimycin |
| Kifunensine |
