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

110165CBC
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      Overview

      Replacement Information

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      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      110165CBC-25MG
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          Glass bottle 25 mg
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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®
          Synonyms1,2-Dideoxy-2ʹ-ethylamino-α-D-glucopyranoso-[2,1-d]-2ʹ-thiazoline, OGA Inhibitor, Thiamet-G, (3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol
          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
          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

          Documentation

          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
          Synonyms1,2-Dideoxy-2ʹ-ethylamino-α-D-glucopyranoso-[2,1-d]-2ʹ-thiazoline, OGA Inhibitor, Thiamet-G, (3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol
          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 -20°C
          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.
          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.