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MedKoo Cat#: 563409 | Name: Thiamet G
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Description:

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

Thiamet G is a potent and selective inhibitor of O-GlcNAcase.

Chemical Structure

Thiamet G
Thiamet G
CAS#1009816-48-1

Theoretical Analysis

MedKoo Cat#: 563409

Name: Thiamet G

CAS#: 1009816-48-1

Chemical Formula: C9H16N2O4S

Exact Mass: 248.0831

Molecular Weight: 248.29

Elemental Analysis: C, 43.54; H, 6.50; N, 11.28; O, 25.77; S, 12.91

Price and Availability

Size Price Availability Quantity
10mg USD 125.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 400.00 Ready to ship
100mg USD 650.00 Ready to ship
200mg USD 1,050.00 Ready to ship
500mg USD 2,150.00 Ready to ship
1g USD 3,450.00 Ready to ship
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No Data
Synonym
Thiamet G; Thiamet-G;
IUPAC/Chemical Name
(3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol
InChi Key
PPAIMZHKIXDJRN-FMDGEEDCSA-N
InChi Code
InChI=1S/C9H16N2O4S/c1-2-10-9-11-5-7(14)6(13)4(3-12)15-8(5)16-9/h4-8,12-14H,2-3H2,1H3,(H,10,11)/t4-,5-,6-,7-,8-/m1/s1
SMILES Code
O[C@H]1[C@H](O)[C@@]2([H])N=C(NCC)S[C@@]2([H])O[C@@H]1CO
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
Biological target:
Thiamet G is a potent and selective inhibitor of O-GlcNAcase (OGA), which acts to remove O-GlcNAc from modified proteins, with Ki of 20 nM for human OGA.
In vitro activity:
To further confirm the effect of TMG (Thiamet G ) on polarization of microglia, a polarization experiment was carried out in BV2 cells with or without TMG. BV2 cells were cultivated in medium containing M1 or M2 polarization cytokines in the presence of TMG. After 12 h, no significant change of M2 was observed in TMG-treated groups compared with the MCAO group, although M1 polarization was suppressed by TMG (Figure 5(a) to (d)). These results provide further evidence to assert that TMG influences microglial polarization. The transcriptional activity of NF-κB was also examined during polarization. The data showed that NF-κB was suppressed along with the decreased M1 phenotype trigged by TMG treatment (Figure 5(e) to (h)). After intervention with TMG, less p65 translocated into nuclei even when the amount of p65 in the cytoplasm did not change dramatically, which indicated that the transcriptional activity of p65 was suppressed by TMG (Figure 5(e) and (g), cytoplasmic: 0.52 ± 0.02 in the TMG group vs. 0.45 ± 0.01 in the Control group, ns: not significant, n = 9 per group; Figure 5(f) and (h), nuclear: 0.81 ± 0.06 in TMG group vs. 1.33 ± 0.01 in the Control group, P < 0.05, n = 9 per group). The implication was that TMG may shift the polarization of microglia/macrophages by inhibiting NF-κB activation. Reference: J Cereb Blood Flow Metab. 2017 Aug; 37(8): 2938–2951. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5536801/
In vivo activity:
To assess the effect of TMG (Thiamet G ) on the brain injury after focal ischemia in mice, infarct volumes and neurological deficit scores were quantified at several doses and multiple time points after MCAO. Higher doses (10–40 mg/kg) significantly reduced infarct volumes (Figure 1(a)). These decreases of infarct volume reached significance at 72 h after I/R injury, although the decreased mNSS reached significance at 24 h (Supplemental Figure 1). The following experiments were performed at a dose of 20 mg/kg TMG, and infarct volume was evaluated at 72 h after MCAO. To evaluate the effect of TMG on neuronal function of mice after MCAO, a variety of behavior function tests were executed. All these tests were performed at 24 h after MCAO. Results from mNSS testing exemplified a dramatic change in the MCAO group compared to both TMG-treated groups: 9 (6.5–10.5) in the preventative treatment group vs. 13 (10.5–13.5) in the MCAO group, P < 0.05, n = 9 per group; 6 (4.5–8) in the therapeutic treatment group vs. 13 (10.5– 13.5) in MCAOs, P < 0.01, n = 9 per group (Figure 1(d)). Further functional analyses with the foot-fault test, adhesion-removal test, and inclined plane test also indicated markedly improved outcomes after treatment with TMG in MCAO mice (Figure 1(e) to (g)). Together, these results support the presumption that treatment with TMG is neuroprotective in MCAO mice. Results shown in Figure 1(b) and (c) indicate that treatment with TMG before ischemic injury significantly reduced the infarct size (37.00 ± 0.60 mm3 in the preventative treatment group vs. 52.44 ± 1.00 mm3 in the MCAO group, P < 0.05, n = 9 per group). The therapeutic treatment group yielded virtually the same result (38.11 ± 1.60 mm3 vs. 52.44 ± 1.00 mm3 in the MCAO group, P < 0.05, n = 9 per group). Reference: J Cereb Blood Flow Metab. 2017 Aug; 37(8): 2938–2951. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5536801/
Solvent mg/mL mM comments
Solubility
DMSO 32.0 128.99
H2O 50.0 201.55
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 248.29 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Takeuchi T, Horimoto Y, Oyama M, Nakatani S, Kobata K, Tamura M, Arata Y, Hatanaka T. Osteoclast Differentiation Is Suppressed by Increased O-GlcNAcylation Due to Thiamet G Treatment. Biol Pharm Bull. 2020;43(10):1501-1505. doi: 10.1248/bpb.b20-00221. PMID: 32999159. 2. He Y, Ma X, Li D, Hao J. Thiamet G mediates neuroprotection in experimental stroke by modulating microglia/macrophage polarization and inhibiting NF-κB p65 signaling. J Cereb Blood Flow Metab. 2017 Aug;37(8):2938-2951. doi: 10.1177/0271678X16679671. Epub 2016 Jan 1. PMID: 27864466; PMCID: PMC5536801. 3.Jiang M, Yu S, Yu Z, Sheng H, Li Y, Liu S, Warner DS, Paschen W, Yang W. XBP1 (X-Box-Binding Protein-1)-Dependent OGlcNAcylation Is Neuroprotective in Ischemic Stroke in Young Mice and Its Impairment in Aged Mice Is Rescued by Thiamet-G. Stroke. 2017 Jun;48(6):1646-1654. doi: 10.1161/STROKEAHA.117.016579. Epub 2017 May 9. PMID: 28487326; PMCID: PMC5493893.
In vitro protocol:
1. Takeuchi T, Horimoto Y, Oyama M, Nakatani S, Kobata K, Tamura M, Arata Y, Hatanaka T. Osteoclast Differentiation Is Suppressed by Increased O-GlcNAcylation Due to Thiamet G Treatment. Biol Pharm Bull. 2020;43(10):1501-1505. doi: 10.1248/bpb.b20-00221. PMID: 32999159. 2. He Y, Ma X, Li D, Hao J. Thiamet G mediates neuroprotection in experimental stroke by modulating microglia/macrophage polarization and inhibiting NF-κB p65 signaling. J Cereb Blood Flow Metab. 2017 Aug;37(8):2938-2951. doi: 10.1177/0271678X16679671. Epub 2016 Jan 1. PMID: 27864466; PMCID: PMC5536801.
In vivo protocol:
1. He Y, Ma X, Li D, Hao J. Thiamet G mediates neuroprotection in experimental stroke by modulating microglia/macrophage polarization and inhibiting NF-κB p65 signaling. J Cereb Blood Flow Metab. 2017 Aug;37(8):2938-2951. doi: 10.1177/0271678X16679671. Epub 2016 Jan 1. PMID: 27864466; PMCID: PMC5536801. 2. Jiang M, Yu S, Yu Z, Sheng H, Li Y, Liu S, Warner DS, Paschen W, Yang W. XBP1 (X-Box-Binding Protein-1)-Dependent OGlcNAcylation Is Neuroprotective in Ischemic Stroke in Young Mice and Its Impairment in Aged Mice Is Rescued by Thiamet-G. Stroke. 2017 Jun;48(6):1646-1654. doi: 10.1161/STROKEAHA.117.016579. Epub 2017 May 9. PMID: 28487326; PMCID: PMC5493893.
1: Domenico FD, Lanzillotta C, Prestia F, Tramutola A, Barone E, Perluigi M. Basic Science and Pathogenesis. Alzheimers Dement. 2024 Dec;20 Suppl 1:e086816. doi: 10.1002/alz.086816. PMID: 39751020. 2: Garcia ML, McMahon LL, Jackson NL. Basic Science and Pathogenesis. Alzheimers Dement. 2024 Dec;20 Suppl 1:e093507. doi: 10.1002/alz.093507. PMID: 39750578. 3: Holicek V, Deen M, Bhosale S, Ashmus RA, Vocadlo DJ. An Efficient and Accessible Hectogram-Scale Synthesis for the Selective O-GlcNAcase Inhibitor Thiamet-G. ACS Omega. 2024 Dec 8;9(50):49223-49228. doi: 10.1021/acsomega.4c06141. PMID: 39713709; PMCID: PMC11656354. 4: Xu L, Liu B, Ma H, Qi E, Ma J, Chang T, Zhang J, Zhang W, Chen W, Cao X, Xiong X. O-GlcNAc transferase promotes vascular smooth muscle calcification through modulating Wnt/β-catenin signaling. FASEB J. 2024 Dec 13;38(24):e70271. doi: 10.1096/fj.202401649RR. PMID: 39704274. 5: Liu G, Li H, Feng L, Li M, Gao P, Wang F. O-GlcNAcylation promotes astroglial-mesenchymal transition via the connexin43 pathway under high-glucose conditions. Exp Eye Res. 2024 Dec 11;251:110206. doi: 10.1016/j.exer.2024.110206. Epub ahead of print. PMID: 39672530. 6: Li C, Qian Z, Zhang H, Ge X, Chen L, Xue M, Tang T, He Z, Zheng L, Cao C, Zhang K, Ma R, Yao B. O-GlcNAc participates in the meiosis of aging oocytes by mediating mitochondrial function. Reproduction. 2024 Nov 14;168(6):e240138. doi: 10.1530/REP-24-0138. PMID: 39405070; PMCID: PMC11623119. 7: Bell M, Kane MS, Ouyang X, Young ME, Jegga AG, Chatham JC, Darley-Usmar V, Zhang J. Acute increase of protein O-GlcNAcylation in mice leads to transcriptome changes in the brain opposite to what is observed in Alzheimer's Disease. bioRxiv [Preprint]. 2024 Sep 20:2024.09.19.613769. doi: 10.1101/2024.09.19.613769. PMID: 39345543; PMCID: PMC11429956. 8: Kramer J, Chatham JC, Young ME, Darley-Usmar V, Zhang J. Impact of O -GlcNAcylation elevation on mitophagy and glia in the dentate gyrus. bioRxiv [Preprint]. 2024 Sep 20:2024.09.19.613771. doi: 10.1101/2024.09.19.613771. PMID: 39345468; PMCID: PMC11430020. 9: Alghusen IM, Carman MS, Wilkins HM, Strope TA, Gimore C, Fedosyuk H, Shawa J, Ephrame SJ, Denson AR, Wang X, Swerdlow RH, Slawson C. O-GlcNAc impacts mitophagy via the PINK1-dependent pathway. Front Aging Neurosci. 2024 Aug 8;16:1387931. doi: 10.3389/fnagi.2024.1387931. PMID: 39175808; PMCID: PMC11339348. 10: Loaeza-Reyes KJ, Zenteno E, Ramírez-Hernández E, Salinas-Marin R, Moreno- Rodríguez A, Torres-Rosas R, Argueta-Figueroa L, Fernández-Rojas B, Pina-Canseco S, Acevedo-Mascarúa AE, Hernández-Antonio A, Pérez-Cervera Y. The modulation of the hexosamine biosynthetic pathway impacts the localization of CD36 in macrophages. Acta Biochim Pol. 2024 Jul 8;71:13004. doi: 10.3389/abp.2024.13004. PMID: 39041003; PMCID: PMC11261345. 11: Zhou W, Tang Q, Wang S, Ding L, Chen M, Liu H, Wu Y, Xiong X, Shen Z, Chen W. Local thiamet-G delivery by a thermosensitive hydrogel confers ischemic cardiac repair via myeloid M2-like activation in a STAT6 O-GlcNAcylation- dependent manner. Int Immunopharmacol. 2024 Apr 20;131:111883. doi: 10.1016/j.intimp.2024.111883. Epub 2024 Mar 18. PMID: 38503016. 12: Wu QP, Vang S, Zhou JQ, Krick S, Barnes JW, Sanders YY. O-GlcNAc regulates anti-fibrotic genes in lung fibroblasts through EZH2. J Cell Mol Med. 2024 Apr;28(7):e18191. doi: 10.1111/jcmm.18191. PMID: 38494860; PMCID: PMC10945079. 13: Yaqin Z, Kehan W, Yi Z, Naijian W, Wei Q, Fei M. Resveratrol alleviates inflammatory bowel disease by inhibiting JAK2/STAT3 pathway activity via the reduction of O-GlcNAcylation of STAT3 in intestinal epithelial cells. Toxicol Appl Pharmacol. 2024 Mar;484:116882. doi: 10.1016/j.taap.2024.116882. Epub 2024 Mar 2. PMID: 38437956. 14: Alghusen IM, Carman MS, Wilkins H, Ephrame SJ, Qiang A, Dias WB, Fedosyuk H, Denson AR, Swerdlow RH, Slawson C. O-GlcNAc regulates the mitochondrial integrated stress response by regulating ATF4. Front Aging Neurosci. 2023 Dec 18;15:1326127. doi: 10.3389/fnagi.2023.1326127. PMID: 38192280; PMCID: PMC10773771. 15: Zhang CC, Li Y, Jiang CY, Le QM, Liu X, Ma L, Wang FF. O-GlcNAcylation mediates H2O2-induced apoptosis through regulation of STAT3 and FOXO1. Acta Pharmacol Sin. 2024 Apr;45(4):714-727. doi: 10.1038/s41401-023-01218-z. Epub 2024 Jan 8. PMID: 38191912; PMCID: PMC10943090. 16: Liu G, Feng L, Liu X, Gao P, Wang F. O-GlcNAcylation Inhibition Upregulates Connexin43 Expression in the Endothelium to Protect the Tight Junction Barrier in Diabetic Retinopathy. Invest Ophthalmol Vis Sci. 2023 Nov 1;64(14):30. doi: 10.1167/iovs.64.14.30. PMID: 37982762; PMCID: PMC10668625. 17: Yu F, Zhang Z, Leng Y, Chen AF. O-GlcNAc modification of GSDMD attenuates LPS-induced endothelial cells pyroptosis. Inflamm Res. 2024 Jan;73(1):5-17. doi: 10.1007/s00011-023-01812-1. Epub 2023 Nov 14. PMID: 37962578; PMCID: PMC10776498. 18: Cook BE, Nag S, Arakawa R, Lin EY, Stratman N, Guckian K, Hering H, Lulla M, Choi J, Salinas C, Genung NE, Morén AF, Bolin M, Boscutti G, Plisson C, Martarello L, Halldin C, Kaliszczak MA. Development of a PET Tracer for OGA with Improved Kinetics in the Living Brain. J Nucl Med. 2023 Oct;64(10):1588-1593. doi: 10.2967/jnumed.122.265225. Epub 2023 Jul 6. PMID: 37934021. 19: Su WC, Hung CF, Wang YC, Peng H, Huang WH, Lo YL, Lo YH, Chen YC, Su HH, Chen YL. Thiamet G as a Potential Treatment for Polycystic Kidney Disease. In Vivo. 2023 Nov-Dec;37(6):2524-2532. doi: 10.21873/invivo.13360. PMID: 37905652; PMCID: PMC10621443. 20: Silva-Aguiar RP, Teixeira DE, Peres RAS, Alves SAS, Novaes-Fernandes C, Dias WB, Pinheiro AAS, Peruchetti DB, Caruso-Neves C. O-Linked GlcNAcylation mediates the inhibition of proximal tubule (Na++K+)ATPase activity in the early stage of diabetes mellitus. Biochim Biophys Acta Gen Subj. 2023 Nov;1867(11):130466. doi: 10.1016/j.bbagen.2023.130466. Epub 2023 Sep 22. PMID: 37742874.