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Kifunensine

Cat No.:V21586 Purity: ≥98%
Kifunensine is a potent and specific inhibitor of class I α-mannosidases extracted from actinomycetes that blocks α-mannosidases I from trimming mannose residues on glycoproteins.
Kifunensine
Kifunensine Chemical Structure CAS No.: 109944-15-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
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Product Description
Kifunensine is a potent and specific inhibitor of class I α-mannosidases extracted from actinomycetes that blocks α-mannosidases I from trimming mannose residues on glycoproteins. Kifunensine inhibits endoplasmic reticulum-associated protein degradation pathways.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
The actinomycete Kitasatosporia kifunense 9482 is the source of the alkaloid kifunensine. It can inhibit N-glycan synthesis at the an8GlcNAc2 (Man8) or Man9GlcNAc2 (Man9) stage and is the most potent α-mannosidase I inhibitor [3].
Cell Assay
RT-PCR[3]
Cell Types: hybridoma cells expressing human IgG1 monoclonal antibody [3].
Tested Concentrations: 2 micrograms/ml.
Incubation Duration: 4 days.
Experimental Results: Significant reduction in lentil lectin binding. Kifunensine was the most effective of the inhibitors tested in producing antibodies containing oligomannose residues but no fucose.
Animal Protocol
Animal/Disease Models: BALB/c mouse[3].
Doses: 5 mg/kg.
Route of Administration: intravenously (iv) (iv)(iv) via tail vein.
Experimental Results: There were no significant differences in serum levels of anti-TEM B mAb produced by cells treated with or without kifunensine over a 7-day period.
References

[1]. Glycoform Modification of Secreted Recombinant Glycoproteins through Kifunensine Addition during Transient Vacuum Agroinfiltration. Int J Mol Sci. 2018 Mar; 19(3): 890.

[2]. Structure of Kifunensine, a New Immunomodulator Isolated from an Actinomycete. J. Org. Chem. 1989,54,4015-4016.

[3]. 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]. 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.

Additional Infomation
Kifunensine has been reported in Kitasatospora kifunensis with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H12N2O6
Molecular Weight
232.19068
Exact Mass
232.069
CAS #
109944-15-2
PubChem CID
130611
Appearance
White to off-white solid powder
Density
1.9±0.1 g/cm3
Melting Point
>280℃
Index of Refraction
1.706
LogP
-2.21
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
1
Heavy Atom Count
16
Complexity
335
Defined Atom Stereocenter Count
5
SMILES
C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H]2N1C(=O)C(=O)N2)O)O)O)O
InChi Key
OIURYJWYVIAOCW-PQMKYFCFSA-N
InChi Code
InChI=1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1
Chemical Name
(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridine-2,3-dione
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~11.9 mg/mL (~51.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.19 mg/mL (5.13 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 11.9 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.19 mg/mL (5.13 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 11.9 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 1.19 mg/mL (5.13 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 11.9 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.3068 mL 21.5341 mL 43.0682 mL
5 mM 0.8614 mL 4.3068 mL 8.6136 mL
10 mM 0.4307 mL 2.1534 mL 4.3068 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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