B1027-5g | 2-Deoxy-D-glucose [154-17-6] Clinisciences

2-Deoxy-D-glucose (2DG), glucose analogue, is a competitive glycolytic inhibitor [1] [2] [3]. Cytotoxicity assays displayed IC50 values of 2DG in KIT-positive GIST cell lines between 0.5μM (GIST882 cell line) and 2.5μM (GIST430 cell line) [4].
Glycolysis is an ATP-producing subsystem [5].
If the physiologically relevant ratio of 2DG/glucose is 0.8, the glucose metabolism in the FaDu cells that are growing in DMEM containing 25 mmol/L glucose will be inhibited. Treatment with 2DG caused a 30% to 40% decrease in total glutathione content and 32% cell killing relative to untreated control cells [2]. 2-DG inhibited PEDV propagation in a concentration-dependent manner and induced endoplasmic reticulum stress in Vero cells. The 2-DG treatment did not significantly affect virus entry. But further research showed that 2-DG decreased viral protein translation, implying that 2-DG might affect virus replication at the early stage of virus infection. Additionally, the 2-DG treatment increased the expression level of CD13 [6].
2-Deoxy-D-glucose increases the efficacy of adriamycin and paclitaxel in human osteosarcoma and non-small cell lung cancers in vivo in retarding tumor growth and prolonging survival [3]. In Sparus aurata L., 2-DG increased blood glucose levels in a statistically significant way, caused a non-statistically significant decrease in the respiratory burst activity of head kidney leucocytes. Peroxidase activity measured in serum and head kidney leukocyte showed no statistically significant difference with respect to the control values [7].
References:
[1]. John Laszlo, William R. Harlan, Robert F. Klein, et al. The Effect of 2-Deoxy-D-Glucose Infusions on Lipid and Carbohydrate Metabolism in Man. J Clin Invest., 1961, 40(1):171-176.
[2]. Andrean L. Simons, Iman M. Ahmad, David M. Mattson, et al. 2-Deoxy-D-Glucose Combined with Cisplatin Enhances Cytotoxicity via Metabolic Oxidative Stress in Human Head and NeckCancer Cells. Cancer Research, 2007, 67(7): 3364-3371.
[3]. Gregory Maschek, Niramol Savaraj, Waldemar Priebe, et al. 2-Deoxy-D-glucose Increases the Efficacy of Adriamycin and Paclitaxel in Human Osteosarcoma and Non-Small Cell Lung Cancers In Vivo. Cancer Research, 2004, 64:31-34.
[4]. Thomas Mühlenberg, Susanne Grunewald, Jürgen Treckmann, et al. Inhibition of KIT-Glycosylation by 2-Deoxyglucose Abrogates KIT-Signaling and Combination with ABT-263 Synergistically Induces Apoptosis in Gastrointestinal Stromal Tumor. PLOS ONE, 2015, 10(3):e0120531.
[5]. R. J. Connett, C. R. Honig, T. E. Gayeski, et al. Defining hypoxia: a systems view of VO2, glycolysis, energetics, and intracellular PO2. Journal of Applied Physiology, 1990, 68(3): 833-842.
[6]. Yue Wang, Jia-rong Li, Ming-xia Sun, et al. Triggering unfolded protein response by 2-Deoxy-D-glucose inhibits porcine epidemic diarrhea virus propagation. Antiviral Research, 2014, 106: 33–41.
[7]. F.A. Guardiola, R. Cerezuela, J. Meseguer, et al. Effects of 2-deoxy-D-glucose on the immune system of seabream (Sparus aurata L.). Fish & Shellfish Immunology, 2011, 30: 592-599.

1. Wanli Liu, et al. "MCT1-governed pyruvate metabolism is essential for antibody class-switch recombination through H3K27 acetylation." Nat Commun. 2024 Jan 2;15(1):163. PMID: 38167945
2. Méghane Sittewelle, Stephen J Royle, et al. "Passive diffusion accounts for the majority of intracellular nanovesicle transport." Life Sci Alliance. 2023 Oct 19;7(1):e202302406. PMID: 37857498
3. Ren He, Xiaohan Li, et al. "Dexamethasone inhibits IL-8 via glycolysis and mitochondria-related pathway to regulate inflammatory pain." BMC Anesthesiol. 2023 Sep 18;23(1):317. PMID: 37723417
4. Xiaofeng Li, Yiwen Chen, et al. "GPR81-mediated reprogramming of glucose metabolism contributes to the immune landscape in breast cancer." Discov Oncol. 2023 Jul 27;14(1):140. PMID: 37500811
5. Xu-Zhe Fu, Yu Wang, et al. "Interferon-γ regulates immunosuppression in septic mice by promoting the Warburg effect through the PI3K/AKT/mTOR pathway." Mol Med. 2023 Jul 11;29(1):95. PMID: 37434129
6. Yiman He, Huawan Chen, et al. "3-Bromopyruvate-loaded bismuth sulfide nanospheres improve cancer treatment by synergizing radiotherapy with modulation of tumor metabolism." J Nanobiotechnology. 2023 Jul 5;21(1):209. PMID: 37408010
7. Joshua Saliutama. "Fatty Acids and Parasitism: Towards a Better Understanding of Lipid Metabolism in Trypanosoma Brucei." Clemson University. August 2023.
8. Ye Liu, Wenna Chi, et al. "Ablation of Proton/glucose Exporter SLC45A2 Enhances Melanosomal Glycolysis to Inhibit Melanin Biosynthesis and Promote Melanoma Metastasis." J Invest Dermatol. 2022 Apr 23;S0022-202X(22)00301-3. PMID: 35469906
9. Fang Wang, Jing Zhang, et al. "2-Deoxy-D-glucose impedes T cell-induced apoptosis of keratinocytes in oral lichen planus." J Cell Mol Med. 2021 Nov;25(21):10257-10267. PMID: 34672419
10. Beatriz Lapa, Ana Cristina Gonçalves, et al. "Acute myeloid leukemia sensitivity to metabolic inhibitors: glycolysis showed to be a better therapeutic target." Med Oncol. 2020 Jul 28;37(8):72. PMID: 32725458
11. Wang F, Zhang J, et al. "HIF1α/PLD2 axis linked to glycolysis induces T-cell immunity in oral lichen planus." Biochim Biophys Acta Gen Subj. 2020;1864(7):129602. PMID: 32205175
12. Wang F, Zhang J, et al. "The mTOR-glycolytic pathway promotes T-cell immunobiology in oral lichen planus." Immunobiology. 2020;225(3):151933. PMID: 32201095
13. Li X, Zhang Y, et al. "Enhanced glucose metabolism mediated by CD147 contributes to immunosuppression in hepatocellular carcinoma." Cancer Immunol Immunother. 2020;10.1007/s00262-019-02457-y. PMID: 31965268
14. Barot S, Abo-Ali EM, et al. "Inhibition of glycogen catabolism induces intrinsic apoptosis and augments multikinase inhibitors in hepatocellular carcinoma cells." Exp Cell Res. 2019 Aug 15;381(2):288-300. PMID: 31128107
15. Tian C, Yuan Z, et al. "Inhibition of glycolysis by a novel EGFR/HER2 inhibitor KU004 suppresses the growth of HER2+ cancer." Exp Cell Res. 2017 May 19. pii: S0014-4827(17)30297-5. PMID: 28532652

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Storage	Store at -20°C
M.Wt	164.16
Cas No.	154-17-6
Formula	C₆H₁₂O₅
Solubility	≥105 mg/mL in H2O; ≥2.37 mg/mL in EtOH with gentle warming and ultrasonic; ≥8.2 mg/mL in DMSO
Chemical Name	(4R,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol
SDF	Download SDF
Canonical SMILES	06[C@]([C@](C1(06)06)(06)O06)([C@](C(06)(06)O06)(06)OC1(06)O06)O06
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Cell experiment [1, 2]:
Cell lines	GIST cell lines, Vero cells infected with PEDV
Preparation method	The solubility of this compound in DMSO is >8.2 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.
Reacting condition	5 mM, 10 mM, 24 h
Applications	2DG dose-dependent accumulation of cells in G1 phase and reduction of S phase cells with the IC50 values between 0.5 μM and 2.5 μM. 2-DG inhibited PEDV replication and gene expression in Vero cells. 2-DG (10 mM for 24 h) treatment affected virus packaging.
Animal experiment [3]:
Animal models	Nude mouse xenograft models of human osteosarcoma and non-small cell lung cancer
Dosage form	500 mg/kg, i.p., 3 × per week (Monday, Wednesday, and Friday)
Application	ADR (6 mg/kg, i.v.) + 2-DG (500 mg/kg, i.p.) combination treatment resulted in significant slower tumor growth than 2-DG alone.
Other notes	Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.
References: [1]. Mühlenberg T, Grunewald S, Treckmann J, et al. Inhibition of KIT-glycosylation by 2-deoxyglucose abrogates KIT-signaling and combination with ABT-263 synergistically induces apoptosis in gastrointestinal stromal tumor[J]. PloS one, 2015, 10(3): e0120531. [2]. Wang Y, Li J, Sun M, et al. Triggering unfolded protein response by 2-Deoxy-D-glucose inhibits porcine epidemic diarrhea virus propagation[J]. Antiviral research, 2014, 106: 33-41. [3]. Gregory Maschek, Niramol Savaraj, Waldemar Priebe, et al. 2-Deoxy-D-glucose Increases the Efficacy of Adriamycin and Paclitaxel in Human Osteosarcoma and Non-Small Cell Lung Cancers In Vivo. Cancer Research, 2004, 64:31-34.