GlcNAc-硒唑啉抑制 OGA。
OGA inhibition by GlcNAc-selenazoline.
机构信息
Department of Science Education-Chemistry Major, Daegu University, Gyeongbuk 712-714, Republic of Korea.
出版信息
Bioorg Med Chem. 2010 Oct 1;18(19):7058-64. doi: 10.1016/j.bmc.2010.08.010. Epub 2010 Aug 11.
Abstract
The title compound, which differs from the powerful O-GlcNAcase (OGA) inhibitor GlcNAc-thiazoline only at the chalcogen atom (Se for S), is a much weaker inhibitor in a direct OGA assay. In human cells, however, the selenazoline shows comparable ability to induce hyper-O-GlcNAc-ylation, and the two show similar reduction of insulin-stimulated translocation of glucose transporter 4 in differentiated 3T3 adipocytes.
摘要
标题化合物与强效 O-GlcNAcase（OGA）抑制剂 GlcNAc-噻唑啉仅在硫属原子（Se 代替 S）上有所不同，在直接 OGA 测定中，它是一种弱得多的抑制剂。然而，在人类细胞中，硒唑啉显示出相当的诱导高 O-GlcNAc 化的能力，并且两者在分化的 3T3 脂肪细胞中显示出相似的减少胰岛素刺激的葡萄糖转运蛋白 4 的易位。
相似文献
1
OGA inhibition by GlcNAc-selenazoline.
Bioorg Med Chem. 2010 Oct 1;18(19):7058-64. doi: 10.1016/j.bmc.2010.08.010. Epub 2010 Aug 11.
2
Tautomeric modification of GlcNAc-thiazoline.
Org Lett. 2007 Jun 7;9(12):2321-4. doi: 10.1021/ol0706814. Epub 2007 May 18.
3
Inhibition of O-GlcNAcase using a potent and cell-permeable inhibitor does not induce insulin resistance in 3T3-L1 adipocytes.
Chem Biol. 2010 Sep 24;17(9):937-48. doi: 10.1016/j.chembiol.2010.07.006.
4
N-Acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines.
Bioorg Med Chem Lett. 2008 May 1;18(9):2944-7. doi: 10.1016/j.bmcl.2008.03.067. Epub 2008 Mar 28.
5
Inhibition of O-GlcNAcase in perfused rat hearts by NAG-thiazolines at the time of reperfusion is cardioprotective in an O-GlcNAc-dependent manner.
Am J Physiol Heart Circ Physiol. 2010 Nov;299(5):H1715-27. doi: 10.1152/ajpheart.00337.2010. Epub 2010 Sep 10.
6
GlcNAc-Thiazoline conformations.
Bioorg Med Chem. 2009 Mar 1;17(5):1831-6. doi: 10.1016/j.bmc.2009.01.066. Epub 2009 Feb 3.
7
GlcNAcstatins are nanomolar inhibitors of human O-GlcNAcase inducing cellular hyper-O-GlcNAcylation.
Biochem J. 2009 May 13;420(2):221-7. doi: 10.1042/BJ20090110.
8
Structural insights into the mechanism and inhibition of eukaryotic O-GlcNAc hydrolysis.
EMBO J. 2006 Apr 5;25(7):1569-78. doi: 10.1038/sj.emboj.7601026. Epub 2006 Mar 16.
9
Distinctive inhibition of O-GlcNAcase isoforms by an alpha-GlcNAc thiolsulfonate.
J Am Chem Soc. 2007 Dec 5;129(48):14854-5. doi: 10.1021/ja076038u. Epub 2007 Nov 10.
10
Role of the O-GlcNAc modification on insulin resistance and endoplasmic reticulum stress in 3T3-L1 cells.
Mol Biol Rep. 2020 Aug;47(8):5927-5942. doi: 10.1007/s11033-020-05665-3. Epub 2020 Jul 20.
引用本文的文献
1
Bispecific Thio-Linked Disaccharides as Inhibitors of Pseudomonas Aeruginosa Lectins LecA (PA-IL) and LecB (PA-IIL): Dual-Targeting Strategy.
Chemistry. 2025 Jan 22;31(5):e202403546. doi: 10.1002/chem.202403546. Epub 2024 Nov 28.
2
Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from .
Molecules. 2021 Jan 21;26(3):542. doi: 10.3390/molecules26030542.
3
An enzymatic route to selenazolines.
Chembiochem. 2013 Mar 18;14(5):564-7. doi: 10.1002/cbic.201300037. Epub 2013 Feb 18.
4
The roles of O-linked β-N-acetylglucosamine in cardiovascular physiology and disease.
Am J Physiol Heart Circ Physiol. 2012 May 15;302(10):H1905-18. doi: 10.1152/ajpheart.00445.2011. Epub 2012 Jan 27.
5
Detection and analysis of proteins modified by O-linked N-acetylglucosamine.
Curr Protoc Protein Sci. 2011 Nov;Chapter 12:12.8.1-12.8.33. doi: 10.1002/0471140864.ps1208s66.
6
Detection and analysis of proteins modified by O-linked N-acetylglucosamine.
Curr Protoc Mol Biol. 2011 Jul;Chapter 17:Unit 17.6. doi: 10.1002/0471142727.mb1706s95.
本文引用的文献
1
Enhanced Nrf2-dependent induction of glutathione in mouse embryonic fibroblasts by isoselenocyanate analog of sulforaphane.
Bioorg Med Chem Lett. 2010 Apr 15;20(8):2675-9. doi: 10.1016/j.bmcl.2010.01.044. Epub 2010 Jan 20.
2
Synthesis and characterization of a novel iNOS/Akt inhibitor Se,Se'-1,4-phenylenebis(1,2-ethanediyl)bisisoselenourea (PBISe)--against colon cancer.
Bioorg Med Chem Lett. 2010 Mar 15;20(6):2038-43. doi: 10.1016/j.bmcl.2009.09.071. Epub 2009 Sep 22.
3
Visualizing the reaction coordinate of an O-GlcNAc hydrolase.
J Am Chem Soc. 2010 Feb 17;132(6):1807-9. doi: 10.1021/ja9086769.
4
Probing synergy between two catalytic strategies in the glycoside hydrolase O-GlcNAcase using multiple linear free energy relationships.
J Am Chem Soc. 2009 Sep 23;131(37):13415-22. doi: 10.1021/ja904506u.
5
O-linked beta-N-acetylglucosamine (O-GlcNAc): Extensive crosstalk with phosphorylation to regulate signaling and transcription in response to nutrients and stress.
Biochim Biophys Acta. 2010 Feb;1800(2):96-106. doi: 10.1016/j.bbagen.2009.07.018. Epub 2009 Aug 6.
6
The hexosamine signaling pathway: O-GlcNAc cycling in feast or famine.
Biochim Biophys Acta. 2010 Feb;1800(2):80-95. doi: 10.1016/j.bbagen.2009.07.017. Epub 2009 Jul 30.
7
GlcNAc-Thiazoline conformations.
Bioorg Med Chem. 2009 Mar 1;17(5):1831-6. doi: 10.1016/j.bmc.2009.01.066. Epub 2009 Feb 3.
8
Elevation of global O-GlcNAc levels in 3T3-L1 adipocytes by selective inhibition of O-GlcNAcase does not induce insulin resistance.
J Biol Chem. 2008 Dec 12;283(50):34687-95. doi: 10.1074/jbc.M804525200. Epub 2008 Oct 8.
9
O-GlcNAc regulates FoxO activation in response to glucose.
J Biol Chem. 2008 Jun 13;283(24):16283-92. doi: 10.1074/jbc.M802240200. Epub 2008 Apr 17.
10
N-Acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines.
Bioorg Med Chem Lett. 2008 May 1;18(9):2944-7. doi: 10.1016/j.bmcl.2008.03.067. Epub 2008 Mar 28.
Zotero 插件