Conduritol B epoxide


Catalog No. size PriceQuantity
M7220-2 2mg solid $112
M7220-10 10mg solid $452

Description

Cas:6090-95-5

Product Information

Conduritol B epoxide, also known as CBE, is an inhibitor of non-mammalian and mammalian β-glucosidase. When injected in mice it produces the biochemical and certain clinical and pathological characteristics of Gaucher disease. Conduritol B epoxide is a mechanism-based inhibitor which binds covalently to the catalytic site of acid β-glucosidase.

 

Chemical Formula: C6H10O5 

 

Exact Mass: 162.0528

 

Molecular Weight: 162.141

 

Elemental Analysis: C, 44.45; H, 6.22; O, 49.34

 

Synonym:

 

Conduritol B epoxide

Conduritol-B-epoxide

CBE

 

Chemical Name:

(1R,2R,3S,4S,5R,6S)-7-oxabicyclo[4.1.0]heptane-2,3,4,5-tetrol

 

InChi Key:

ZHMWOVGZCINIHW-FTYOSCRSSA-N

 

InChi Code: InChI=1S/C6H10O5/c7-1-2(8)4(10)6-5(11-6)3(1)9/h1-10H/t1-,2-,3+,4+,5-,6+/m0/s1

 

Smiles Code:

O[C@H]1[C@@]2([H])O[C@@]2([H])[C@H](O)[C@@H](O)[C@@H]1O

 

 

Technical Data:

 

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: >2 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: 2934.99.9001

 

In Vitro

Treating N2a and Conduritol B epoxide-N2a cells with G6 gave GC reductions to 7% and 26% of untreated levels, respectively. G6 treated Conduritol B epoxide-N2a also has significantly decreased GS. Co-treatment of G6 and dantrolene of Conduritol B epoxide-N2a cells lead to a similar degree of GC and GS reduction as G6 alone, indicating a specific effect of G6 on inhibition of substrate accumulation, Conduritol B epoxide-N2a cells have higher calcium levels than in N2a cells without caffeine at baseline. Conduritol B epoxide-N2a cells show a significant increase in cytosolic calcium levels compared to N2a cells. Conduritol B epoxide-N2a cells show a significant reduction in OCR as evidenced by approximately 50% in all the parameters, including rate of ATP production, basal respiration, and maximal respiration, compared to N2a cells, indicating reduced mitochondrial function in this nGD cell model. In dantrolene-treated Conduritol B epoxide-N2a cells, levels of Ryr3 are increased to 76% of WT level.

 

In Vivo

Conduritol B epoxide treatment of 4L, 9H, 9V and WT mice (100 mg/kg/day, i.p.) from postnatal day 5 to 11 does not induce α-synuclein aggregates. Long-term daily Conduritol B epoxide treatment of 4L mice (100 mg/kg/day of Conduritol B epoxide from postnatal day 15 for 24 or 36 doses) leads to hind limb paralysis and small amounts of α-synuclein accumulation in the olfactory bulb, brainstem, and PVP near D3V (dorsal 3rd ventricle).

 

 

References

 

  1. Balreira A, Cavallari M, SaMiranda MC, Arosa FA. Uncoupling between CD1d upregulation induced by retinoic acid and conduritol-B-epoxide and iNKT cell responsiveness. Immunobiology. 2010 Jun;215(6):505-13. doi: 10.1016/j.imbio.2009.07.002. Epub 2009 Aug 3. PubMed PMID: 19651460.

 

  1. Serrano P, Llebaria A, Delgado A. Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide. J Org Chem. 2005 Sep 30;70(20):7829-40. Erratum in: J Org Chem. 2006 Jan 6;71(1):448. PubMed PMID: 16277302.

 

  1. Premkumar L, Sawkar AR, Boldin-Adamsky S, Toker L, Silman I, Kelly JW, Futerman AH, Sussman JL. X-ray structure of human acid-beta-glucosidase covalently bound to conduritol-B-epoxide. Implications for Gaucher disease. J Biol Chem. 2005 Jun 24;280(25):23815-9. Epub 2005 Apr 6. PubMed PMID: 15817452.

 

  1. Newburg DS, Shea TB, Yatziv S, Raghavan SS, McCluer RH. Macrophages exposed in vitro to conduritol B epoxide resemble Gaucher cells. Exp Mol Pathol. 1988 Jun;48(3):317-23. PubMed PMID: 3371456.

 

  1. Grabowski GA, Osiecki-Newman K, Dinur T, Fabbro D, Legler G, Gatt S, Desnick RJ. Human acid beta-glucosidase. Use of conduritol B epoxide derivatives to investigate the catalytically active normal and Gaucher disease enzymes. J Biol Chem. 1986 Jun 25;261(18):8263-9. PubMed PMID: 3087971.

 

Products are for research use only. Not for human use.

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