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110165CBC O-GlcNAcase Inhibitor, TMG - CAS 1009816-48-1 - Calbiochem

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: (3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol, 1,2-Dideoxy-2ʹ-ethylamino-α-D-glucopyranoso-[2,1-d]-2ʹ-thiazoline, OGA Inhibitor, Thiamet-G

110165CBC
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Overview

Replacement Information

Products

Catalog NumberPackaging Qty/Pack
110165CBC-25MG Glass bottle 25 mg
Description
OverviewA cell-permeable, blood-brain barrier-permeant, orally active aminothiazoline that effectively increases O-GlcNAc level of cellular proteins both in cultures (EC50 = 30 nM, ECmax = 200 nM in PC3) in vitro and in rats (50 mg/kg i.v.; 200 mg/kg via drinking water ad libitum) and mice (500 mg/kg via drinking water ad libitum) in vivo by inhibiting O-GlcNAcase/OGA-mediated O-GlcNAc cleavage in a substrate-competitive (Ki = 21 nM), time- and dose-dependent, and highly selective manner. TMG long-term treatment in murine AD model effectively prevents loss of motor neurons and reduces NFTs in brain without apparent effect on Tau hyperphosphorylation. O-GlcNAcylation is also reported to slow down heat-induced sTAB1 (TAK1-binding protein) aggregation and modulate CK2α kinase activity and substrate selectivity in vitro.
Catalogue Number110165CBC
Brand Family Calbiochem®
Synonyms(3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol, 1,2-Dideoxy-2ʹ-ethylamino-α-D-glucopyranoso-[2,1-d]-2ʹ-thiazoline, OGA Inhibitor, Thiamet-G
References
ReferencesYuzwa, S.A., et al. 2012. Nat. Chem. Biol. 8, 393.
Tarrant, M.K., et al. 2012. Nat. Chem. Biol. 8, 262
Yuzwa, S.A., et al. 2008. Nat. Chem. Biol. 4, 483.
Product Information
CAS number1009816-48-1
FormOff-white solid
Hill FormulaC₉H₁₆N₂O₄S
Chemical formulaC₉H₁₆N₂O₄S
Quality LevelMQ100
Applications
Biological Information
Purity≥98% by HPLC
Physicochemical Information
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Harmful
Storage -20°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalog Number GTIN
110165CBC-25MG 04055977208009

Documentation

O-GlcNAcase Inhibitor, TMG - CAS 1009816-48-1 - Calbiochem Certificates of Analysis

TitleLot Number
110165CBC

References

Reference overview
Yuzwa, S.A., et al. 2012. Nat. Chem. Biol. 8, 393.
Tarrant, M.K., et al. 2012. Nat. Chem. Biol. 8, 262
Yuzwa, S.A., et al. 2008. Nat. Chem. Biol. 4, 483.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision04-April-2012 JSW
Synonyms(3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol, 1,2-Dideoxy-2ʹ-ethylamino-α-D-glucopyranoso-[2,1-d]-2ʹ-thiazoline, OGA Inhibitor, Thiamet-G
DescriptionA cell-permeable, stable (no degradation at room temp for 9 days in water), orally available aminothiazoline that effectively increases O-GlcNAc (O-linked β-N-acetylglucosamine) level of cellular proteins both in cultures (EC50 = 30 nM, ECmax = 200 nM in PC3) in vitro and in rats (50 mg/kg i.v.; 200 mg/kg via drinking water ad libitum) and mice (500 mg/kg via drinking water ad libitum) in vivo by inhibiting O-GlcNAcase/OGA-mediated O-GlcNAc cleavage in a substrate-competitive (Ki = 21 nM against pNP-GlcNaAc hydrolysis by human OGA), time- and dose-dependent, and highly selective manner, displaying no effect toward OCT (UDP GlcNAc polypeptidyltransferase) and five other glycoside hydrolases. O-GlcNAc modification is shown to reduce both the kinetics and extent of Tau441 c-terminal fragment Tau244-441 aggregate formation. TMG long-term treatment (36-wk; 500 mg/kg; drinking water ad libitum) of JNPL3 murine AD model bearing mutant human Tau (P301L) results in less NFTs (neurofibrillary tangles) in brain and 40% higher motor neurons in ventral horn without apparent effect on Tau hyperphosphorylation, while short-term treatment (≤24 h) in rats is reported to result in both a decrease in Tau phosphorylation and an increase of Tau O-GlcNAc modification. O-GlcNAcylation is also reported to slow down heat-induced sTAB1 (TAK1-binding protein) aggregation and modulate CK2α kinase activity and substrate selectivity in vitro.
FormOff-white solid
Intert gas (Yes/No) Packaged under inert gas
CAS number1009816-48-1
Chemical formulaC₉H₁₆N₂O₄S
Purity≥98% by HPLC
SolubilityDMSO (100 mg/ml) or H₂O (100 mg/ml)
Storage Protect from light
-20°C
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Toxicity Harmful
ReferencesYuzwa, S.A., et al. 2012. Nat. Chem. Biol. 8, 393.
Tarrant, M.K., et al. 2012. Nat. Chem. Biol. 8, 262
Yuzwa, S.A., et al. 2008. Nat. Chem. Biol. 4, 483.