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

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. 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
2. 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
3. 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
4. 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
5. 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
6. 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
7. 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
8. 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	22[C@]([C@](C1(22)22)(22)O22)([C@](C(22)(22)O22)(22)OC1(22)O22)O22
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.