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2-NBDG
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Identifiers CAS number 186689-07-6 Template loop detected: Template:Chembox entryTemplate loop detected: Template:Chembox entryTemplate loop detected: Template:Chembox entryTemplate loop detected: Template:Chembox entry
2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
PubChem 6711157
This article uses material from the Wikipedia article 2-NBDG, that was deleted or is being discussed for deletion, which is released under the Creative Commons Attribution-ShareAlike 3.0 Unported License.
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This article uses material from the Wikipedia article 2-NBDG, that was deleted or is being discussed for deletion, which is released under the Creative Commons Attribution-ShareAlike 3.0 Unported License.
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
Properties Template loop detected: Template:Chembox entryTemplate loop detected: Template:Chembox entryTemplate loop detected: Template:Chembox entryTemplate loop detected: Template:Chembox entry
2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
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2-NBDG
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references








Supplementary data page Structure and
properties
n, εr, etc. Thermodynamic
data
Phase behaviour
Solid, liquid, gas Spectral data UV, IR, NMR, MS Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

2-NBDG is a fluorescent tracer used for monitoring glucose uptake into living cells; it consists of a glucosamine molecule substituted with a 7-nitrobenzofurazan fluorophore at its amine group. It is widely referred to a fluorescent derivative of glucose,[1] and it is used in cell biology to visualize uptake of glucose by cells.[2] Cells that have taken up the compound fluorescence green.

2-NBDG is similar to radiolabeled glucose in that both can be used to detect glucose transport. Unlike radiolabeled glucose, 2-NBDG is compatible with fluorescence techniques such as a fluorescent microscopy, flow cytometry, and fluorimetry [2]

The compound is taken up by a variety of mammalian, plant, and microbial cells[2][3] In mammalian cells, the transporter for 2-NBDG is GLUT2.[4] In bacterial cells, the predominant transporter is the mannose phosphotransferase system.[5] Cells that lack these or other compatible transporters do not take up 2-NBDG.[5][6]

Similar to glucose, 2-NBDG is transported according to Michaelis-Menten kinetics. However, transport of 2-NBDG has a lower V_\max(maximum rate), and thus the rate of transport is generally slower than glucose.[5]

Once taken up, the compound is metabolized to a non-fluorescent derivative, as shown in Escherichia coli.[7] The identity and further metabolism of this non-fluorescent derivative has not been established.

References

  1. Yoshioka, K; Takahashi, H; Homma, T; Saito, M; Oh, K; Nemoto, Y; Matsuoka, H (1996). "A novel fluorescent derivative of glucose applicable to the assessment of glucose uptake activity of Escherichia coli". Biochim Biophys Acta 1289 (1): 5–9. PMID 8605231. http://www.sciencedirect.com/science/article/pii/0304416595001530. 
  2. 2.0 2.1 2.2 "A real-time method of imaging glucose uptake in single, living mammalian cells". Nat Protoc 2 (3): 753–62. 2007. DOI:10.1038/nprot.2007.76. PMID 17406637. 
  3. "Existence of two parallel mechanisms for glucose uptake in heterotrophic plant cells". J. Exp. Bot. 56 (417): 1905–12. 2005. DOI:10.1093/jxb/eri185. PMID 15911561. 
  4. "Measurement of glucose uptake and intracellular calcium concentration in single, living pancreatic beta-cells". J. Biol. Chem. 275 (29): 22278–83. 2000. DOI:10.1074/jbc.M908048199. PMID 10748091. 
  5. 5.0 5.1 5.2 "Transport of a Fluorescent Analogue of Glucose (2-NBDG) versus Radiolabeled Sugars by Rumen Bacteria and Escherichia coli". Biochemistry 55 (18): 2578–89. 2016. DOI:10.1021/acs.biochem.5b01286. PMID 27096355. 
  6. "Development of a novel non-radioactive cell-based method for the screening of SGLT1 and SGLT2 inhibitors using 1-NBDG". Mol Biosyst 9 (8): 2010–20. 2013. DOI:10.1039/c3mb70060g. PMID 23657801. 
  7. "Intracellular fate of 2-NBDG, a fluorescent probe for glucose uptake activity, in Escherichia coli cells". Biosci. Biotechnol. Biochem. 60 (11): 1899–901. 1996. DOI:10.1271/bbb.60.1899. PMID 8987871. 


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