| Revision as of 12:26, 20 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 08:12, 10 January 2025 edit undoGraeme Bartlett (talk | contribs)Administrators250,106 edits IUPHAR_ligand |
| (29 intermediate revisions by 16 users not shown) |
| Line 1: |
Line 1: |
|
{{Chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 400288292 |
|
| verifiedrevid = 425009413 |
|
| ImageFile = GTPgammaS.png |
|
| ImageFile = GTP-gamma-S.svg |
|
| ImageSize = 300px |
|
| ImageSize = 300px |
|
| IUPACName = methyl dihydroxyphosphinothioyl hydrogen |
|
| IUPACName = methyl dihydroxyphosphinothioyl hydrogen phosphate |
|
⚫ |
|Section1={{Chembox Identifiers |
|
phosphate |
|
|
⚫ |
| CASNo_Ref = {{cascite|correct|??}} |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
|
| CASNo = 37589-80-3 |
| ⚫ |
| CASNo_Ref = {{cascite}} |
|
|
| CASNo = 37589-80-3 |
|
| ChEBI = 43000 |
|
| InChI = 34654 |
|
| ChEMBL = 1204628 |
|
|
| ChemSpiderID = 34654 |
| ⚫ |
| InChI=1/C10H16N5O13P3S/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(26-9)1-25-29(19,20)27-30(21,22)28-31(23,24)32/h2-3,5-6,9,16-17H,1H2,(H,19,20)(H,21,22)(H2,23,24,32)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 |
|
|
|
| DrugBank = DB01864 |
| ⚫ |
| InChIKey = XOFLBQFBSOEHOG-UUOKFMHZBU |
|
|
| PubChem = 37792 |
|
| IUPHAR_ligand = 4207 |
|
|
| KEGG = C01806 |
| ⚫ |
| SMILES = S=P(O)(O)OP(=O)(O)OP(=O)(O)OC3O(n1cnc2c1NC(=N/C2=O)\N)(O)3O |
|
|
|
| UNII = EJ7Q9D2M9D |
|
| MeSHName = |
|
|
|
| InChI = 34654 |
|
⚫ |
| InChI2 = 1/C10H16N5O13P3S/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(26-9)1-25-29(19,20)27-30(21,22)28-31(23,24)32/h2-3,5-6,9,16-17H,1H2,(H,19,20)(H,21,22)(H2,23,24,32)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 |
|
⚫ |
| InChIKey = XOFLBQFBSOEHOG-UUOKFMHZBU |
|
|
| PubChem = 135398675 |
|
⚫ |
| SMILES = S=P(O)(O)OP(=O)(O)OP(=O)(O)OC3O(n1cnc2c1NC(=N/C2=O)\N)(O)3O |
|
⚫ |
}} |
|
⚫ |
|Section2={{Chembox Properties |
|
⚫ |
| C=10 | H=16 | N=5 | O=13 | P=3 | S=1 |
|
⚫ |
| Appearance = |
|
⚫ |
| Density = |
|
⚫ |
| MeltingPt = |
|
⚫ |
| BoilingPt = |
|
⚫ |
}} |
|
⚫ |
|Section3={{Chembox Hazards |
|
⚫ |
| MainHazards = |
|
⚫ |
| FlashPt = |
|
|
| AutoignitionPt = |
|
⚫ |
}} |
|
}} |
|
}} |
|
|
'''GTPgammaS''' (GTPγS, guanosine 5'-O-triphosphate) is a non-hydrolyzable or slowly hydrolyzable ]-activating analog of ] (GTP). Many GTP binding proteins demonstrate activity when bound to GTP, and are inactivated via the hydrolysis of the ] bond that links the γ-phosphate to the remainder of the nucleotide, leaving a bound ] (GDP) and releasing an inorganic ]. This usually occurs rapidly, and the GTP-binding protein can then only be activated by exchanging the GDP for a new GTP molecule.<ref>{{cite journal |last1=Harrison |first1=C. |last2=Traynor |first2=J. R. |date=December 12, 2003 |title=The GTPγS binding assay: approaches and applications in pharmacology |url=https://www.sciencedirect.com/science/article/abs/pii/S0024320503008920 |journal=] |volume=74 |issue=4 |pages=489–508 |doi=10.1016/j.lfs.2003.07.005 |pmid=14609727 |access-date=April 26, 2021 |name-list-style=vanc}}</ref> The substitution of ] for one of the oxygens of the γ-phosphate of GTP creates a nucleotide that either cannot be hydrolyzed or is only slowly hydrolyzed. This prevents the GTP-binding proteins from being inactivated, and allows the cellular processes that they carry out when active to be more easily studied.<ref>{{cite journal |last1=Spoerner |first1=Michael |last2=Nuehs |first2=Andrea |last3=Herrmann |first3=Christian |last4=Steiner |first4=Guido |last5=Kalbitzer |first5=Hans Robert |date=March 2007 |title=Slow conformational dynamics of the guanine nucleotide-binding protein Ras complexed with the GTP analogue GTPγS |journal=] |volume=274 |issue=6 |pages=1419–1433 |doi=10.1111/j.1742-4658.2007.05681.x |pmid=17302736 |name-list-style=vanc|doi-access=free }}</ref> |
| ⚫ |
| Section2 = {{Chembox Properties |
|
| ⚫ |
| C=10|H=16|N=5|O=13|P=3|S=1 |
|
| ⚫ |
| Appearance = |
|
| ⚫ |
| Density = |
|
| ⚫ |
| MeltingPt = |
|
| ⚫ |
| BoilingPt = |
|
| ⚫ |
}} |
|
| ⚫ |
| Section3 = {{Chembox Hazards |
|
|
| Solubility = |
|
| ⚫ |
| MainHazards = |
|
| ⚫ |
| FlashPt = |
|
|
| Autoignition = |
|
| ⚫ |
}} |
|
| ⚫ |
}} |
|
|
'''GTPgammaS''' (GTPγS, guanosine 5'-O-triphosphate) is nonhydrolyzable (although in some cases such as with dynamin it is slowly hydrolyzable) ]-activating analog of ] (GTP). It has many physiological actions such as stimulation of guanine nucleotide-binding proteins, ] ], ]accumulation, and activation of specific ]. Its 35GS labelled radioligand GTPgammaS is used in ] and G-protein binding studies. |
|
|
|
|
|
|
|
The consequences of the constitutive activation of GTP-binding proteins include stimulation of ] ],<ref>{{cite journal |last1=White |first1=H. L. |last2=Scates |first2=P. W. |date=1991 |title=Effects of GTPγS and other nucleotides on phosphoinositide metabolism in crude rat brain synaptosomal preparations |url=https://www.sciencedirect.com/science/article/abs/pii/019701869190170I |journal=] |volume=18 |issue=3 |pages=381–387 |doi=10.1016/0197-0186(91)90170-I |pmid=20504715 |s2cid=44683770 |access-date=April 26, 2021 |name-list-style=vanc}}</ref> ] accumulation or elimination,<ref>{{cite journal |last1=Baker |first1=Stephen P. |last2=Scammells |first2=Peter J. |last3=Belardinelli |first3=Luiz |date=July 2000 |title=Differential A1-adenosine receptor reserve for inhibition of cyclic AMP accumulation and G-protein activation in DDT1 MF-2 cells |journal=] |volume=130 |issue=5 |pages=1156–1164 |doi=10.1038/sj.bjp.0703405 |pmid=10882402 |pmc=1572163 |name-list-style=vanc|doi-access=free }}</ref> and activation of specific ].<ref>{{cite journal |last1=Pennington |first1=Stephen R. |last2=Hesketh |first2=T. Robin |last3=Metcalfe |first3=James C. |date=January 25, 1988 |title=GTPγS activation of proto-oncogene expression in transiently permeabilised Swiss 3T3 fibroblasts |journal=] |volume=227 |issue=2 |pages=203–208 |doi=10.1016/0014-5793(88)80899-8 |pmid=3276558 |name-list-style=vanc|doi-access=free |bibcode=1988FEBSL.227..203P }}</ref> The <sup>35</sup>S labelled radioligand of the compound, <sup>35</sup>SGTPγS, is used in ] and G-protein binding studies.<ref>{{cite journal |last1=Strange |first1=Philip G. |date=November 2010 |title=Use of the GTPγS (GTPγS and Eu-GTPγS) binding assay for analysis of ligand potency and efficacy at G protein-coupled receptors |journal=] |volume=161 |issue=6 |pages=1238–1249 |doi=10.1111/j.1476-5381.2010.00963.x |pmid=20662841 |name-list-style=vanc|pmc=3000650 }}</ref> |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
{{Nucleobases, nucleosides, and nucleotides}} |
|
{{Nucleobases, nucleosides, and nucleotides}} |
|
|
|
|
|
] |
|
] |
|
|
|
|
{{biochem-stub}} |
|
|
|
|
|
] |
|