2-NBDG
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MedKoo CAT#: 584465

CAS#: 186689-07-6

Description: 2-NBDG is a fluorescent derivative of glucose whose uptake is competitively inhibited by D-glucose, but not L-glucose or sucrose, in E. coli. It has been used to monitor glucose uptake by bacteria and live mammalian cells and in tumor biopsies.

Chemical Structure

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2-NBDG
CAS# 186689-07-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584465
Name: 2-NBDG
CAS#: 186689-07-6
Chemical Formula: C12H14N4O8
Exact Mass: 342.08
Molecular Weight: 342.264
Elemental Analysis: C, 42.11; H, 4.12; N, 16.37; O, 37.40

Price and Availability

Size Price Availability Quantity
5mg USD 120 Ready to ship
10mg USD 190 Ready to ship
25mg USD 350 Ready to ship
50mg USD 550 Ready to ship
100mg USD 950 Ready to ship
200mg USD 1650 Ready to ship
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Synonym: 2-NBDG; 2NBDG; 2 NBDG

IUPAC/Chemical Name: 2-(N-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino)-2-deoxyglucopyranoside

InChi Key: GVEBOQDOPLERMC-BGCUHRRXSA-N

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

SMILES Code: OC1[C@H](NC2=CC=C([N+]([O-])=O)C3=NON=C32)[C@H]([C@@H]([C@@H](CO)O1)O)O

Appearance: Red-orange 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: >2 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: 2934.99.9001

More Info:

Biological target: 2-NBDG, a fluorescent D-glucose analog, is a fluorescent indicator for monitoring glucose uptake into living cells.
In vitro activity: Results of high-resolution and widefield imaging of 2-NBDG based molecular contrast in model cell-culture systems are shown in Figure 1. Figure 1 (a) shows the uptake of 2-NBDG in 1483 oral squamous carcinoma cell line; fluorescence is predominantly localized to the cytoplasm. The fluorescence signal from 2-NBDG is significantly higher than the cellular autofluorescence signal from unlabeled cells. Figure 1(b) demonstrates labeling of cells in a tissue culture phantom following topical delivery of 2-NBDG. Reference: Int J Cancer. 2009 Jun 1;124(11):2634-42. https://pubmed.ncbi.nlm.nih.gov/19173294/
In vivo activity: Circulating breast cancer cells with increased uptake of 2-NBDG were detected in the blood samples of tumor-bearing mice following incubation of the blood samples with 2-NBDG and magnetic separation using magnetic beads conjugated with anti-EpCAM IgG. Circulating breast cancer cells with uptake of 2-NBDG were detected not only in the blood samples from the mice bearing visible SKBR-3 xenograft tumors, but also in the blood samples from the mice with no visible tumors after implantation of SKBR-3 tumor cells (Fig. 2a). Circulating breast cancer cells with uptake of 2-NBDG were also detected in the blood samples from the mice bearing MDA-MB-231 xenograft tumors (Fig. 2b), or BT474 xenograft tumors (Fig. 2c). Reference: J Fluoresc. 2013 Jan;23(1):213-20. https://pubmed.ncbi.nlm.nih.gov/23054302/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 29.22
DMSO 37.4 109.30
Ethanol 11.5 33.60
PBS (pH 7.2) 10.0 29.22
Water 3.5 10.23

Preparing Stock Solutions

The following data is based on the product molecular weight 342.26 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. Nitin N, Carlson AL, Muldoon T, El-Naggar AK, Gillenwater A, Richards-Kortum R. Molecular imaging of glucose uptake in oral neoplasia following topical application of fluorescently labeled deoxy-glucose. Int J Cancer. 2009 Jun 1;124(11):2634-42. doi: 10.1002/ijc.24222. PMID: 19173294; PMCID: PMC2700039. 2. Thekkek N, Maru DM, Polydorides AD, Bhutani MS, Anandasabapathy S, Richards-Kortum R. 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. 2011 Oct;10(5):431-41. doi: 10.7785/tcrt.2012.500220. PMID: 21895028; PMCID: PMC4527376. 3. Cai H, Peng F. 2-NBDG fluorescence imaging of hypermetabolic circulating tumor cells in mouse xenograft model of breast cancer. J Fluoresc. 2013 Jan;23(1):213-20. doi: 10.1007/s10895-012-1136-z. Epub 2012 Oct 9. PMID: 23054302; PMCID: PMC4592774. 4. Tsytsarev V, Maslov KI, Yao J, Parameswar AR, Demchenko AV, Wang LV. In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog. J Neurosci Methods. 2012 Jan 15;203(1):136-40. doi: 10.1016/j.jneumeth.2011.09.005. Epub 2011 Sep 14. PMID: 21939688; PMCID: PMC3221836.
In vitro protocol: 1. Nitin N, Carlson AL, Muldoon T, El-Naggar AK, Gillenwater A, Richards-Kortum R. Molecular imaging of glucose uptake in oral neoplasia following topical application of fluorescently labeled deoxy-glucose. Int J Cancer. 2009 Jun 1;124(11):2634-42. doi: 10.1002/ijc.24222. PMID: 19173294; PMCID: PMC2700039. 2. Thekkek N, Maru DM, Polydorides AD, Bhutani MS, Anandasabapathy S, Richards-Kortum R. 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. 2011 Oct;10(5):431-41. doi: 10.7785/tcrt.2012.500220. PMID: 21895028; PMCID: PMC4527376.
In vivo protocol: 1. Cai H, Peng F. 2-NBDG fluorescence imaging of hypermetabolic circulating tumor cells in mouse xenograft model of breast cancer. J Fluoresc. 2013 Jan;23(1):213-20. doi: 10.1007/s10895-012-1136-z. Epub 2012 Oct 9. PMID: 23054302; PMCID: PMC4592774. 2. Tsytsarev V, Maslov KI, Yao J, Parameswar AR, Demchenko AV, Wang LV. In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog. J Neurosci Methods. 2012 Jan 15;203(1):136-40. doi: 10.1016/j.jneumeth.2011.09.005. Epub 2011 Sep 14. PMID: 21939688; PMCID: PMC3221836.

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

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

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

4. N. Thekkek, D. M. Maru, A. D. Polydorides, 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).