| Revision as of 18:44, 16 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wik← Previous edit |
Latest revision as of 05:29, 12 November 2024 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,518 edits templated cite |
| (31 intermediate revisions by 28 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
| ⚫ |
{{drugbox | verifiedrevid = 443611389 |
|
|
|
{{cs1 config|name-list-style=vanc|display-authors=6}} |
|
| |
|
|
|
{{one source|date=June 2017}} |
| ⚫ |
| IUPAC_name = O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino ''N''-phenyl carbamate |
|
|
|
{{drugbox |
|
⚫ |
| verifiedrevid = 450848550 |
|
⚫ |
| IUPAC_name = ''O''-(2-Acetamido-2-deoxy-<small>D</small>-glucopyranosylidene)amino ''N''-phenyl carbamate |
|
| image = pugnac.png |
|
| image = pugnac.png |
|
|
| CAS_number_Ref = {{cascite|correct|CAS}} |
|
| CAS_number = 132489-69-1 |
|
| CAS_number = 132489-69-1 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = AWZ7VE64B6 |
|
| ATC_prefix = |
|
| ATC_prefix = |
|
| ATC_suffix = |
|
| ATC_suffix = |
|
| PubChem = 9576811 |
|
| PubChem = 9576811 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = |
|
| DrugBank = |
|
| C=15 | H=19 | N=3 | O=7 |
|
| C=15 | H=19 | N=3 | O=7 |
|
| molecular_weight = 353.33 |
|
|
| bioavailability = |
|
| bioavailability = |
|
| protein_bound = |
|
| protein_bound = |
| Line 27: |
Line 32: |
|
}} |
|
}} |
|
|
|
|
|
'''PUGNAc''' is a 1,5-hydroximolactone, acting as an ] of a variety of ]. It was long thought that increased levels of ''O''-GlcNAc in human cells lead to Type II diabetes. O-GlcNAc levels were artificially raised with PUGNAc, which inhibits O-GlcNAcase, a beta-exo-N-acetylhexosaminidase which cleaves beta-O-linked-N-acetylglucosamine residues from glycoproteins. As a result of this inhibition, a type II diabetic phenotype was observed. It was unknown however, whether it was the increased O-GlcNAc levels or inhibition of another N-acetylhexosaminidase within the cell which was generating this phenotype. Recent studies have shown, using a selective O-GlcNAcase inhibitor, that there is no corellation between increased ''O''-GlcNAc levels on glycoproteins and Type II diabetes. |
|
'''PUGNAc''' is a 1,5-hydroximolactone, acting as an ] of a variety of ].<ref>{{cite book | vauthors = Cox NJ, Meister TR, Boyce M | chapter = Chemical biology of O-GlcNAc glycosylation | chapter-url = https://books.google.com/books?id=WmwoDwAAQBAJ&dq=PUGNAc&pg=PT102 | veditors = Tan Z, Wang LX|title=Chemical biology of glycoproteins |date= March 2017 |location=United Kingdom | publisher = Royal Society of Chemistry | doi = 10.1039/9781782623823-00094 |isbn=978-1-78801-122-8}}</ref> It was long thought that increased levels of ] in human cells lead to ]. O-GlcNAc levels were artificially raised with PUGNAc, which inhibits O-GlcNAcase, a beta-exo-N-acetylhexosaminidase which cleaves beta-O-linked-N-acetylglucosamine residues from glycoproteins. As a result of this inhibition, a type II diabetic phenotype was observed. Recent pharmacological studies using a more selective O-GlcNAcase inhibitor did not see this effect. However, genetic manipulation of O-GlcNAc levels is consistent with the effects observed by PUGNAc, namely insulin resistance upon elevation of O-GlcNAc levels.<ref>{{Cite journal | vauthors = Cheng SS, Mody AC, Woo CM |date=2024-11-07 |title=Opportunities for Therapeutic Modulation of O-GlcNAc |journal=Chemical Reviews |language=en |doi=10.1021/acs.chemrev.4c00417 |issn=0009-2665}}</ref> |
|
|
|
|
|
==Fictional references== |
|
==Fictional references== |
|
PUGNAc was used by ] in the television series '']'' to keep his ] level high to appear ] and to be resistant to insulin shots he was receiving but did not need. |
|
PUGNAc was used by ] in the television series '']'' to keep his ] level high to appear diabetic.<ref>Season 1, episode 1</ref> |
|
|
|
|
|
|
==References== |
|
== External links == |
|
|
|
{{Reflist}} |
|
* |
|
|
|
|
|
|
== Further reading == |
|
|
{{refbegin}} |
|
|
* {{cite journal | vauthors = Vosseller K, Wells L, Lane MD, Hart GW | title = Elevated nucleocytoplasmic glycosylation by O-GlcNAc results in insulin resistance associated with defects in Akt activation in 3T3-L1 adipocytes | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 99 | issue = 8 | pages = 5313–8 | date = April 2002 | pmid = 11959983 | pmc = 122766 | doi = 10.1073/pnas.072072399 }} |
|
|
{{refend}} |
|
|
|
|
|
{{DEFAULTSORT:Pugnac}} |
|
{{DEFAULTSORT:Pugnac}} |
| Line 42: |
Line 52: |
|
|
|
|
|
{{gastrointestinal-drug-stub}} |
|
{{gastrointestinal-drug-stub}} |
|
|
|
|
] |
|