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Revision as of 17:18, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465214312 of page 2-Deoxy-D-glucose for the Chem/Drugbox validation project (updated: '').  Latest revision as of 15:01, 18 May 2024 edit Nthep (talk | contribs)Autopatrolled, Administrators110,583 edits Copyvio revdel completed (RR)Tag: Manual revert 
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{{DISPLAYTITLE:2-Deoxy-<small>D</small>-glucose}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 446636166 | verifiedrevid = 477213198
| Name = 2-Deoxy-<small>D</small>-glucose | Name = 2-Deoxy-{{sm|d}}-glucose
| Reference =<ref>''Merck Index'', 11th Edition, '''2886'''.</ref> | Reference =<ref>''Merck Index'', 11th Edition, '''2886'''.</ref>
| ImageFile = 2-Deoxy-D-glucose.png | ImageFile = 2-Deoxy-D-glucose.png
| ImageSize = 200px | ImageSize =
| ImageName = 2-Deoxy-D-glucose | ImageName = 2-Deoxy-D-glucose
| IUPACName = 2-Deoxy-<small>D</small>-''arabino''-hexopyranose
| IUPACName = (4''R'',5''S'',6''R'')-6-(hydroxymethyl)oxane-2,4,5-triol |SystematicName=(4''R'',5''S'',6''R'')-6-(hydroxymethyl)oxane-2,4,5-triol
| OtherNames = 2-Deoxyglucose<br />2-Deoxy-<small>D</small>-mannose<br />2-Deoxy-<small>D</small>-arabino-hexose<br />2-DG | OtherNames = 2-Deoxyglucose<br />2-Deoxy-{{sm|d}}-mannose<br />2-Deoxy-{{sm|d}}-arabino-hexose<br />2-DG
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| IUPHAR_ligand = 4643
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 154-17-6 | CASNo = 154-17-6
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9G2MP84A8W | UNII = 9G2MP84A8W
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 388402 | ChemSpiderID = 388402
| PubChem = 108223
| EC_number = 205-823-0
| ChEMBL = 2074932
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/m1/s1 | StdInChI = 1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/m1/s1
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| SMILES = O(C(CO)O(O)C1)1O | SMILES = O(C(CO)O(O)C1)1O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>12</sub>O<sub>5</sub> | Formula = C<sub>6</sub>H<sub>12</sub>O<sub>5</sub>
| MolarMass = 164.16 g/mol | MolarMass = 164.16 g/mol
| Density = | Density =
| MeltingPtC = 142 to 144
| MeltingPt = 142–144&nbsp;°C
| MeltingPt_notes =
}} }}
}} }}

'''2-Deoxy-{{sm|d}}-glucose''' is a ] ] which has the 2-] group replaced by hydrogen, so that it cannot undergo further ]. As such; it acts to competitively inhibit the production of ] from glucose at the ] level (step 2 of glycolysis).<ref>{{cite journal | last1 = Wick | first1 = AN | last2 = Drury | first2 = DR | last3 = Nakada | first3 = HI | last4 = Wolfe | first4 = JB | year = 1957 | title = Localization of the primary metabolic block produced by 2-deoxyglucose | url = http://www.jbc.org/content/224/2/963.full.pdf | journal = J Biol Chem| volume = 224 | issue = 2| pages = 963–969 | doi = 10.1016/S0021-9258(18)64988-9 | pmid=13405925| doi-access = free }}</ref> 2-Deoxyglucose labeled with ] or ] has been a popular ligand for laboratory research in animal models, where distribution is assessed by tissue-slicing followed by ]y, sometimes in tandem with either conventional or ].

2-DG is up taken by the ]s of the cell.<ref>{{cite journal|last1=Laussel|first1=Clotilde|last2=Léon|first2=Sébastien|date=December 2020|title=Cellular toxicity of the metabolic inhibitor 2-deoxyglucose and associated resistance mechanisms|journal=Biochemical Pharmacology|language=en|volume=182|pages=114213|doi=10.1016/j.bcp.2020.114213|pmid=32890467 |doi-access=free}}</ref> Therefore, cells with higher glucose uptake, for example tumor cells, have also a higher uptake of 2-DG. Since 2-DG hampers cell growth, its use as a ] therapeutic has been suggested, and in fact, 2-DG is in clinical trials.<ref>{{cite journal | last1 = Pelicano | first1 = H | last2 = Martin | first2 = DS | last3 = Xu | first3 = RH | last4 = Huang | first4 = P | year = 2006 | title = Glycolysis inhibition for anticancer treatment | journal = Oncogene | volume = 25 | issue = 34| pages = 4633–4646 | doi=10.1038/sj.onc.1209597 | pmid=16892078| title-link = Glycolysis | doi-access = | s2cid = 22155169 }}</ref> It is not completely clear how 2-DG inhibits cell growth. The fact that glycolysis is inhibited by 2-DG, seems not to be sufficient to explain why 2-DG treated cells stop growing.<ref>{{cite journal | doi = 10.1073/pnas.0803090105| pmid = 19004802| pmc = 2584745| title = A catabolic block does not sufficiently explain how 2-deoxy-D-glucose inhibits cell growth| journal = Proceedings of the National Academy of Sciences| volume = 105| issue = 46| pages = 17807–17811| year = 2008| last1 = Ralser| first1 = M.| last2 = Wamelink| first2 = M. M.| last3 = Struys| first3 = E. A.| last4 = Joppich| first4 = C.| last5 = Krobitsch| first5 = S.| last6 = Jakobs| first6 = C.| last7 = Lehrach| first7 = H.| bibcode = 2008PNAS..10517807R| doi-access = free}}</ref> A synergistic effect between 2-DG and various other agents have been reported in the pursuit of anticancer strategies.<ref>{{cite journal |last1=Cheng |first1=Gang |last2=Zielonka |first2=Jacek |last3=Dranka |first3=Brian P. |last4=McAllister |first4=Donna |last5=Mackinnon |first5=A. Craig |last6=Joseph |first6=Joy |last7=Kalyanaraman |first7=Balaraman |date=2012-05-15 |title=Mitochondria-Targeted Drugs Synergize with 2-Deoxyglucose to Trigger Breast Cancer Cell Death |url=https://aacrjournals.org/cancerres/article/72/10/2634/575828/Mitochondria-Targeted-Drugs-Synergize-with-2 |journal=Cancer Research |language=en |volume=72 |issue=10 |pages=2634–2644 |doi=10.1158/0008-5472.CAN-11-3928 |issn=0008-5472 |pmc=3700358 |pmid=22431711}}</ref><ref>{{cite journal |last1=Luo |first1=Zhangyi |last2=Xu |first2=Jieni |last3=Sun |first3=Jingjing |last4=Huang |first4=Haozhe |last5=Zhang |first5=Ziqian |last6=Ma |first6=Weina |last7=Wan |first7=Zhuoya |last8=Liu |first8=Yangwuyue |last9=Pardeshi |first9=Apurva |last10=Li |first10=Song |date=March 2020 |title=Co-delivery of 2-Deoxyglucose and a glutamine metabolism inhibitor V9302 via a prodrug micellar formulation for synergistic targeting of metabolism in cancer |journal=Acta Biomaterialia |language=en |volume=105 |pages=239–252 |doi=10.1016/j.actbio.2020.01.019 |pmc=7105957 |pmid=31958597}}</ref><ref>{{cite journal |last1=Abebe |first1=Felagot A. |last2=Hopkins |first2=Megan D. |last3=Vodnala |first3=Suraj N. |last4=Sheaff |first4=Robert J. |last5=Lamar |first5=Angus A. |date=2021-07-20 |title=Development of a Rapid In Vitro Screening Assay Using Metabolic Inhibitors to Detect Highly Selective Anticancer Agents |journal=ACS Omega |language=en |volume=6 |issue=28 |pages=18333–18343 |doi=10.1021/acsomega.1c02203 |issn=2470-1343 |pmc=8296616 |pmid=34308064}}</ref> Because of its structural similarity to mannose, 2DG has the potential to inhibit N-glycosylation in mammalian cells and other systems, and as such induces ER stress and the Unfolded Protein Response (UPR) pathway.<ref>{{cite journal|last1=Kurtoglu|first1=M.|last2=Gao|first2=N.|last3=Shang|first3=J.|last4=Maher|first4=J. C.|last5=Lehrman|first5=M. A.|last6=Wangpaichitr|first6=M.|last7=Savaraj|first7=N.|last8=Lane|first8=A. N.|last9=Lampidis|first9=T. J.|date=2007-11-07|title=Under normoxia, 2-deoxy-D-glucose elicits cell death in select tumor types not by inhibition of glycolysis but by interfering with N-linked glycosylation|journal=Molecular Cancer Therapeutics|volume=6|issue=11|pages=3049–3058|doi=10.1158/1535-7163.mct-07-0310|pmid=18025288|issn=1535-7163|doi-access=|s2cid=6315384 }}</ref><ref>{{cite journal|last1=Xi|first1=Haibin|last2=Kurtoglu|first2=Metin|last3=Liu|first3=Huaping|last4=Wangpaichitr|first4=Medhi|last5=You|first5=Min|last6=Liu|first6=Xiongfei|last7=Savaraj|first7=Niramol|last8=Lampidis|first8=Theodore J.|date=2010-07-01|title=2-Deoxy-d-glucose activates autophagy via endoplasmic reticulum stress rather than ATP depletion|journal=Cancer Chemotherapy and Pharmacology|volume=67|issue=4|pages=899–910|doi=10.1007/s00280-010-1391-0|pmid=20593179|issn=0344-5704|pmc=3093301}}</ref><ref name=":0">{{cite journal|last1=Defenouillère|first1=Quentin|last2=Verraes|first2=Agathe|last3=Laussel|first3=Clotilde|last4=Friedrich|first4=Anne|last5=Schacherer|first5=Joseph|last6=Léon|first6=Sébastien|date=2019-09-03|title=The induction of HAD-like phosphatases by multiple signaling pathways confers resistance to the metabolic inhibitor 2-deoxyglucose|journal=Science Signaling|volume=12|issue=597|pages=eaaw8000|doi=10.1126/scisignal.aaw8000|pmid=31481524|s2cid=201829818|issn=1945-0877|url=https://hal.archives-ouvertes.fr/hal-03064377/file/Defenouillere%20HAL.pdf}}</ref>

== Use in optical imaging ==
2-DG has been used as a targeted optical imaging agent for fluorescent ''in vivo'' imaging.<ref>{{cite journal | doi = 10.1016/j.ab.2008.09.050 | pmid = 18938129 | title = Characterization and performance of a near-infrared 2-deoxyglucose optical imaging agent for mouse cancer models | journal = Analytical Biochemistry | volume = 384 | issue = 2 | pages = 254–262 | year = 2009 | last1 = Kovar | first1 = Joy L. | last2 = Volcheck | first2 = William | last3 = Sevick-Muraca | first3 = Eva | last4 = Simpson | first4 = Melanie A. | last5 = Olive | first5 = D. Michael | pmc = 2720560 | url = http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1037&context=biochemfacpub }}</ref><ref>Cheng, Z., Levi, J., Xiong, Z., Gheysens, O., Keren, S., Chen, X., and Gambhir, S., Bioconjugate Chemistry, 17(3), (2006), 662-669</ref> In clinical medical imaging (]ning), ] is used, where one of the 2-hydrogens of 2-deoxy-D-glucose is replaced with the positron-emitting isotope ], which emits paired ]s, allowing distribution of the tracer to be imaged by external gamma camera(s). This is increasingly done in tandem with a ] function which is part of the same PET/CT machine, to allow better localization of small-volume tissue glucose-uptake differences.

== Indian adoption for COVID-19 treatment ==
On May 8, 2021, the ] approved an oral formulation of 2-deoxy-D-glucose for emergency use as adjunct therapy in moderate to severe coronavirus patients.<ref>, The Economic Times, 17 May 2021.</ref><ref name=":1">{{cite web|date=2021-05-08|title=DCGI approves anti-COVID drug developed by DRDO for emergency use|url=https://pib.gov.in/PressReleasePage.aspx?PRID=1717007|access-date=2021-05-09|website=Press Information Bureau, Government of India|language=en-IN}}</ref>
The drug was developed by the ] along with ], who jointly claimed via a press release, that the drug "helps in faster recovery of hospitalised patients and reduces supplemental oxygen dependence".<ref name=":1" /><ref name=":2">{{cite web|last=Borana|first=Ronak|date=2021-05-12|title=India's Drug Regulator Has Approved DRDO's New COVID Drug on Missing Evidence|url=https://science.thewire.in/the-sciences/dcgi-drdo-2-dg-covid-19-treatment-phase-2-3-trials-shoddy-evidence/|access-date=2021-05-18|website=The Wire Science|language=en-GB}}</ref><ref name=":3">{{cite news|last=Koshy|first=Jacob|date=2021-05-11|title=Questions remain on DRDO's COVID drug|language=en-IN|work=The Hindu|url=https://www.thehindu.com/news/national/questions-remain-on-drdos-covid-drug/article34537596.ece|access-date=2021-05-18|issn=0971-751X}}</ref> ] as well as ] noted that the approval was based on poor evidence; no journal publication (or ]) concerning efficacy and safety are yet available.<ref name=":2" /><ref name=":3" />

== See also ==
* ]
* ]

==References==
<references/>

{{DEFAULTSORT:Deoxy-D-Glucose, 2-}}
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