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

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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      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
      HS Code2934 99 99
      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
      Catalogue 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.