A fluorescent derivative of glucose
Related Products
Contained In
600470Glucose Uptake Cell-Based Assay Kit
Isomer(s)
139616-NBDG
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2-NBDG

Item No. 11046

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose
CAS Number
186689-07-6
Synonyms
  • NBD-Glucose
Molecular Formula
C12H14N4O8
Formula Weight
342.3
Purity
≥98% (mixture of α and β)
Emission
550 nm
Excitation
475 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
228, 266, 332, 465 nm
SMILES
O[C@H]([C@@H](CO)OC(O)[C@@H]1NC2=CC=C([N+]([O-])=O)C3=NON=C32)[C@@H]1O
InChi Code
InChI=1S/C12H14N4O8/c17-3-6-10(18)11(19)9(12(20)23-6)13-4-1-2-5(16(21)22)8-7(4)14-24-15-8/h1-2,6,9-13,17-20H,3H2/t6-,9-,10-,11-,12?/m1/s1
InChi Key
GVEBOQDOPLERMC-BGCUHRRXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    2-NBDG is a fluorescent derivative of glucose whose uptake is competitively inhibited by D-glucose (Item No. 23733), but not L-glucose (Item No. 20829) or sucrose, in E. coli.1 It has been used to monitor glucose uptake by bacteria and live mammalian cells and in tumor biopsies.1,2,3,4 2-NBDG displays excitation/emission maxima of 475/550 nm, respectively.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshioka, K., Takahashi, H., Homma, T., et al. A novel fluorescent derivative of glucose applicable to the assessment of glucose uptake activity of Escherichia coli. Biochim. Biophys. Acta 1289(1), 5-9 (1996).

    2. Yamada, K., Saito, M., Matsuoka, H., et al. A real-time method of imaging glucose uptake in single, living mammalian cells. Nat. Protoc. 2(3), 753-763 (2007).

    3. Nitin, N., Carlson, A.L., Muldoon, T., et al. Molecular imaging of glucose uptake in oral neoplasia following topical application of fluorescently labeled deoxy-glucose. Int. J. Cancer 124(11), 1-20 (2009).

    4. Thekkek, N., Maru, D.M., Polydorides, A.D., et al. Pre-clinical evaluation of fluorescent deoxyglucose as a topical contrast agent for the detection of Barrett’s-associated neoplasia during confocal imaging. Technol. Cancer Res. Treat. 10(5), 431-441 (2011).

    Product Citations

    Manzo, T., Prentice, B.M., Anderson, K.G., et al. Accumulation of long-chain fatty acids in the tumor microenvironment drives dysfunction in intrapancreatic CD8+ T cells. J. Exp. Med. 217(8), e20191920 (2020).