2-NBDG [2-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)Amino)-2-Deoxyglucose] CAS#: 186689-07-6

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Physical properties

Molecular weight	342.26
Solvent	DMSO

Spectral properties

Excitation (nm)	467
Emission (nm)	538

Storage, safety and handling

H-phrase	H303, H313, H333
Hazard symbol	XN
Intended use	Research Use Only (RUO)
R-phrase	R20, R21, R22
Storage	Freeze (< -15 °C); Minimize light exposure
UNSPSC	12352200

Overview SDS Protocol

CAS

186689-07-6

Molecular weight

342.26

Excitation (nm)

467

Emission (nm)

538

2-NBDG is a fluorescently-labeled deoxyglucose analog that is used primarily to directly monitor glucose uptake by living cells and tissues. It is also used as a topical contrast reagent for the detection of neoplasia. 2-NBDG can be used in real-time confocal, high-resolution, or wide-field fluorescence microscopy as well as in flow cytometry. The probe can be excited by the Argon laser at 488 nm to give the environment-sensitive fluorescence. It has lower photostability than the rhodamine-based fluorescent probes.

Calculators

Common stock solution preparation

Table 1. Volume of DMSO needed to reconstitute specific mass of 2-NBDG [2-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)Amino)-2-Deoxyglucose] *CAS#: 186689-07-6* to given concentration. Note that volume is only for preparing stock solution. Refer to sample experimental protocol for appropriate experimental/physiological buffers.

	0.1 mg	0.5 mg	1 mg	5 mg	10 mg
1 mM	292.176 µL	1.461 mL	2.922 mL	14.609 mL	29.218 mL
5 mM	58.435 µL	292.176 µL	584.351 µL	2.922 mL	5.844 mL
10 mM	29.218 µL	146.088 µL	292.176 µL	1.461 mL	2.922 mL

Molarity calculator

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Spectrum

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Spectral properties

Excitation (nm)	467
Emission (nm)	538

Product Family

Name	Excitation (nm)	Emission (nm)
2-Aminoacridone CAS 27918-14-5	429	529
BTA-2 [2-(4'-(dimethylamino)phenyl)-6-methyl-benzothiazole]	355	426

Images

Figure 1. Chemical structure for 2-NBDG [2-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)Amino)-2-Deoxyglucose] *CAS#: 186689-07-6*

Citations

View all 9 citations: Citation Explorer

GLP-1RA Liraglutide and Semaglutide Improves Obesity-Induced Muscle Atrophy via SIRT1 Pathway
Authors: Xiang, Jie and Qin, Liyan and Zhong, Jinling and Xia, Ning and Liang, Yuzhen
Journal: Diabetes, Metabolic Syndrome and Obesity (2023): 2433--2446

FGF21 alleviates adipose stem cell senescence via CD90 glycosylation-dependent glucose influx in remodeling healthy white adipose tissue
Authors: Zhou, Zixin and Zhang, Huiying and Tao, Yan and Zang, Jinhao and Zhao, Jingyuan and Li, Huijie and Wang, Yalin and Wang, Tianci and Zhao, Hui and Wang, Fuwu and others,
Journal: Redox Biology (2023): 102877

Inhibition of human CD8+ T cells by the tumor metabolite methylthioadenosine: Mechanisms of action and putative strategies to improve antitumor activity
Authors: Strobl, Carolin Dorothea
Journal: (2022)

Selective PRMT5 inhibitors suppress human CD8+ T cells by upregulation of p53 and impairment of the AKT pathway similar to the tumor metabolite MTA
Authors: Strobl, Carolin Dorothea and Schaffer, Stefanie and Haug, Tabea and V{\"o}lkl, Simon and Peter, Katrin and Singer, Katrin and B{\"o}ttcher, Martin and Mougiakakos, Dimitrios and Mackensen, Andreas and Aigner, Michael
Journal: Molecular cancer therapeutics (2020): 409--419

Metabolische und funktionelle Modulation von Effektor-T-Zellen durch humane doppelt-negative T-Zellen
Authors: Haug, Tabea
Journal: (2020)

Human double-negative regulatory T-cells induce a metabolic and functional switch in effector T-cells by suppressing mTOR activity
Authors: Haug, Tabea and Aigner, Michael and Peuser, Moritz M and Strobl, Carolin D and Hildner, Kai and Mougiakakos, Dimitrios and Bruns, Heiko and Mackensen, Andreas and V{\"o}lkl, Simon
Journal: Frontiers in immunology (2019): 883

NT1014, a novel biguanide, inhibits ovarian cancer growth in vitro and in vivo
Authors: Zhang, Lu and Han, Jianjun and Jackson, Am and a L , undefined and Clark, Leslie N and Kilgore, Joshua and Guo, Hui and Livingston, Nick and Batchelor, Kenneth and Yin, Yajie and Gilliam, Timothy P and others, undefined
Journal: Journal of Hematology & Oncology (2016): 91

Glutamine promotes ovarian cancer cell proliferation through the mTOR/S6 pathway
Authors: Yuan, Lingqin and Sheng, Xiugui and Willson, Adam K and Roque, Dario R and Stine, Jessica E and Guo, Hui and Jones, Hannah M and Zhou, Chunxiao and Bae-Jump, Victoria L
Journal: Endocrine-related cancer (2015): 577--591

Label-free optical metabolic imaging of adipose tissues for prediabetes diagnosis
Authors: Chen, Liping and Qin, Guihui and Liu, Yuhong and Li, Moxin and Li, Yue and Guo, Lun-Zhang and Du, Lidong and Zheng, Weiming and Wu, Pei-Chun and Chuang, Yueh-Hsun and others,

References

View all 14 references: Citation Explorer

Transport of a Fluorescent Analogue of Glucose (2-NBDG) versus Radiolabeled Sugars by Rumen Bacteria and Escherichia coli
Authors: Tao J, Diaz RK, Teixeira CR, Hackmann TJ.
Journal: Biochemistry (2016): 2578

2-NBDG as a marker for detecting glucose uptake in reactive astrocytes exposed to oxygen-glucose deprivation in vitro
Authors: Chen Y, Zhang J, Zhang XY.
Journal: J Mol Neurosci (2015): 126

2-NBDG fluorescence imaging of hypermetabolic circulating tumor cells in mouse xenograft model of breast cancer
Authors: Cai H, Peng F.
Journal: J Fluoresc (2013): 213

Syzygium aqueum leaf extract and its bioactive compounds enhances pre-adipocyte differentiation and 2-NBDG uptake in 3T3-L1 cells
Authors: Manaharan T, Ming CH, Palanisamy UD.
Journal: Food Chem (2013): 354

In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog
Authors: Tsytsarev V, Maslov KI, Yao J, Parameswar AR, Demchenko AV, Wang LV.
Journal: J Neurosci Methods (2012): 136

2-NBDG, a fluorescent analogue of glucose, as a marker for detecting cell electropermeabilization in vitro
Authors: Raeisi E, Mir LM.
Journal: J Membr Biol (2012): 633

Uptake of 2-NBDG as a method to monitor therapy response in breast cancer cell lines
Authors: Millon SR, Ostr and er JH, Brown JQ, Raheja A, Seewaldt VL, Ramanujam N.
Journal: Breast Cancer Res Treat (2011): 55

Syntheses of 2-NBDG analogues for monitoring stereoselective uptake of D-glucose
Authors: Yamamoto T, Tanaka S, Suga S, Watanabe S, Nagatomo K, Sasaki A, Nishiuchi Y, Teshima T, Yamada K.
Journal: Bioorg Med Chem Lett (2011): 4088

Uptake of 2-NBDG by human breast cancer cells in vitro
Authors: Hu H, Shan XH, Zhu W, Qian H, Xu WR, Wang YF.
Journal: Zhonghua Zhong Liu Za Zhi (2010): 507

2-NBDG as a fluorescent indicator for direct glucose uptake measurement
Authors: Zou C, Wang Y, Shen Z.
Journal: J Biochem Biophys Methods (2005): 207