Kifunensine | CAS#109944-15-2 | α-mannosidases inhibitor

MedKoo Cat#: 558514 | Name: Kifunensine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Kifunensine is potent and selective inhibitor of class I α-mannosidases and may serve as a key inhibitor of glycoprotein biosynthesis. Its inhibitory action leads to the high mannose glycoproteins in cell culture.

Chemical Structure

Kifunensine

CAS#109944-15-2

Theoretical Analysis

MedKoo Cat#: 558514

Name: Kifunensine

CAS#: 109944-15-2

Chemical Formula: C8H12N2O6

Exact Mass: 232.0700

Molecular Weight: 232.19

Elemental Analysis: C, 41.38; H, 5.21; N, 12.07; O, 41.34

Price and Availability

Size	Price	Availability	Quantity
2mg	USD 350.00	2 Weeks

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Related CAS #

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Synonym

Kifunensine;

IUPAC/Chemical Name

Imidazo(1,2-a)pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R-(5alpha,6beta,7alpha,8alpha,8aalpha))-

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

SMILES Code

O=C1N[C@]2([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)N2C1=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 232.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Chen H, Li R, Liu Z, Wei S, Zhang H, Li X. Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase. Carbohydr Res. 2013 Jan 10;365:1-8. doi: 10.1016/j.carres.2012.10.017. Epub 2012 Oct 27. PubMed PMID: 23159373. 2: Hering KW, Karaveg K, Moremen KW, Pearson WH. A practical synthesis of kifunensine analogues as inhibitors of endoplasmic reticulum alpha-mannosidase I. J Org Chem. 2005 Nov 25;70(24):9892-904. PubMed PMID: 16292820. 3: Elbein AD, Tropea JE, Mitchell M, Kaushal GP. Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I. J Biol Chem. 1990 Sep 15;265(26):15599-605. PubMed PMID: 2144287. 4: Izumi S, Okuhara M. [FK506 and kifunensine, new immunomodulators of microbial origin]. Tanpakushitsu Kakusan Koso. 1993 Aug;38(11):1800-12. Review. Japanese. PubMed PMID: 7692469. 5: Yu C, Crispin M, Sonnen AF, Harvey DJ, Chang VT, Evans EJ, Scanlan CN, Stuart DI, Gilbert RJ, Davis SJ. Use of the α-mannosidase I inhibitor kifunensine allows the crystallization of apo CTLA-4 homodimer produced in long-term cultures of Chinese hamster ovary cells. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2011 Jul 1;67(Pt 7):785-9. doi: 10.1107/S1744309111017672. Epub 2011 Jun 30. PubMed PMID: 21795794; PubMed Central PMCID: PMC3144796. 6: Elbein AD, Kerbacher JK, Schwartz CJ, Sprague EA. Kifunensine inhibits glycoprotein processing and the function of the modified LDL receptor in endothelial cells. Arch Biochem Biophys. 1991 Jul;288(1):177-84. PubMed PMID: 1898016. 7: Weng S, Spiro RG. Endoplasmic reticulum kifunensine-resistant alpha-mannosidase is enzymatically and immunologically related to the cytosolic alpha-mannosidase. Arch Biochem Biophys. 1996 Jan 1;325(1):113-23. PubMed PMID: 8554335. 8: Shah N, Kuntz DA, Rose DR. Comparison of kifunensine and 1-deoxymannojirimycin binding to class I and II alpha-mannosidases demonstrates different saccharide distortions in inverting and retaining catalytic mechanisms. Biochemistry. 2003 Dec 2;42(47):13812-6. PubMed PMID: 14636047. 9: Wen X, Yuan Y, Kuntz DA, Rose DR, Pinto BM. A combined STD-NMR/molecular modeling protocol for predicting the binding modes of the glycosidase inhibitors kifunensine and salacinol to Golgi alpha-mannosidase II. Biochemistry. 2005 May 10;44(18):6729-37. PubMed PMID: 15865418. 10: Weng S, Spiro RG. Demonstration that a kifunensine-resistant alpha-mannosidase with a unique processing action on N-linked oligosaccharides occurs in rat liver endoplasmic reticulum and various cultured cells. J Biol Chem. 1993 Dec 5;268(34):25656-63. PubMed PMID: 8245001. 11: Hudlicky T, Rouden J, Luna H, Allen S. Microbial oxidation of aromatics in enantiocontrolled synthesis. 2. Rational design of aza sugars (endo-nitrogenous). Total synthesis of +-kifunensine, mannojirimycin, and other glycosidase inhibitors. J Am Chem Soc. 1994 Jun;116(12):5099-107. doi: 10.1021/ja00091a011. PubMed PMID: 20000784. 12: Gomes J, Gomes-Alves P, Carvalho SB, Peixoto C, Alves PM, Altevogt P, Costa J. Extracellular Vesicles from Ovarian Carcinoma Cells Display Specific Glycosignatures. Biomolecules. 2015 Aug 4;5(3):1741-61. doi: 10.3390/biom5031741. PubMed PMID: 26248080; PubMed Central PMCID: PMC4598773. 13: Males A, Raich L, Williams SJ, Rovira C, Davies GJ. Conformational Analysis of the Mannosidase Inhibitor Kifunensine: A Quantum Mechanical and Structural Approach. Chembiochem. 2017 Aug 4;18(15):1496-1501. doi: 10.1002/cbic.201700166. Epub 2017 Jun 26. PubMed PMID: 28493500. 14: Soheili T, Gicquel E, Poupiot J, N'Guyen L, Le Roy F, Bartoli M, Richard I. Rescue of sarcoglycan mutations by inhibition of endoplasmic reticulum quality control is associated with minimal structural modifications. Hum Mutat. 2012 Feb;33(2):429-39. doi: 10.1002/humu.21659. Epub 2011 Dec 22. PubMed PMID: 22095924. 15: Yu M, Brown D, Reed C, Chung S, Lutman J, Stefanich E, Wong A, Stephan JP, Bayer R. Production, characterization, and pharmacokinetic properties of antibodies with N-linked mannose-5 glycans. MAbs. 2012 Jul-Aug;4(4):475-87. doi: 10.4161/mabs.20737. Epub 2012 Jul 1. PubMed PMID: 22699308; PubMed Central PMCID: PMC3499342. 16: Hüttner S, Veit C, Vavra U, Schoberer J, Dicker M, Maresch D, Altmann F, Strasser R. A context-independent N-glycan signal targets the misfolded extracellular domain of Arabidopsis STRUBBELIG to endoplasmic-reticulum-associated degradation. Biochem J. 2014 Dec 15;464(3):401-11. doi: 10.1042/BJ20141057. PubMed PMID: 25251695; PubMed Central PMCID: PMC4255730. 17: Babajani G, Kermode AR. Alteration of the proteostasis network of plant cells promotes the post-endoplasmic reticulum trafficking of recombinant mutant (L444P) human β-glucocerebrosidase. Plant Signal Behav. 2014;9(3):e28714. Epub 2014 Apr 8. PubMed PMID: 24713615; PubMed Central PMCID: PMC4091198. 18: van Berkel PH, Gerritsen J, van Voskuilen E, Perdok G, Vink T, van de Winkel JG, Parren PW. Rapid production of recombinant human IgG With improved ADCC effector function in a transient expression system. Biotechnol Bioeng. 2010 Feb 1;105(2):350-7. doi: 10.1002/bit.22535. PubMed PMID: 19739094. 19: Liu WC, Lin YL, Spearman M, Cheng PY, Butler M, Wu SC. Influenza Virus Hemagglutinin Glycoproteins with Different N-Glycan Patterns Activate Dendritic Cells In Vitro. J Virol. 2016 Jun 10;90(13):6085-6096. doi: 10.1128/JVI.00452-16. Print 2016 Jul 1. PubMed PMID: 27099319; PubMed Central PMCID: PMC4907228. 20: Zhou Q, Shankara S, Roy A, Qiu H, Estes S, McVie-Wylie A, Culm-Merdek K, Park A, Pan C, Edmunds T. Development of a simple and rapid method for producing non-fucosylated oligomannose containing antibodies with increased effector function. 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