| Identification | Back Directory | [Name]
GUANIDINOETHYL SULFONATE | [CAS]
543-18-0 | [Synonyms]
NSC 667063
Taurocyamin
TAUROCYAMINE
Amidinotaurine
N-Guanyltaurine
N-Amidinotaurine
taurocyamine zwitterion
GUANIDINOETHYL SULFONATE
Guanidinoethanesulfonic Acid
2-GUANIDINOETHANE SULFONIC ACID
2-Guanylaminoethanesulfonic Acid
2-[(Aminoiminomethyl)amino]thanesulfonic Acid
2-(diaminomethylideneamino)ethanesulfonic acid
2-([AMINO(IMINO)METHYL]AMINO)ETHANE-1-SULFONIC ACID
2-{[amino(imino)methyl]amino}ethane-1-sulphonic acid | [Molecular Formula]
C3H9N3O3S | [MDL Number]
MFCD00084865 | [MOL File]
543-18-0.mol | [Molecular Weight]
167.19 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
263-265°C | [density ]
1.73±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Very Slightly, Heated), Methanol (Very Slightly, Heated), Water (Heated) | [form ]
Solid | [pka]
1.31±0.50(Predicted) | [color ]
White to Off-White | [CAS DataBase Reference]
543-18-0 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A potent inhibitor of taurine transport | [Definition]
ChEBI: Zwitterionic form of taurocyamine arising from transfer of a proton from the sulfo to the guanidino group; major species at pH 7.3. | [Description]
Guanidinoethyl sulfonate, also known as taurocyamine, is a natural guanidine-taurine analog derived from taurine. It is an intermediate of taurine and hypotaurine metabolism and is phosphorylated by taurocyamine kinase. Guanidinoethyl sulfonate competitively inhibits taurine uptake by sodium-dependent taurine transporters in rat hepatocytes (Ki = 1.75 mM). It also acts as a competitive glycine receptor antagonist in mouse striatal neurons. Plasma levels of guanidinoethyl sulfonate are significantly increased in patients with chronic renal failure. | [in vitro]
guanidinoethyl sulphonate was found to be an analogue of taurine and an inhibitor of taurine transport. guanidinoethyl sulphonate was also shown to be a weak agonist at gaba(a) receptors, and was able to antagonize gaba-evoked responses. guanidinoethyl sulphonate did not gate glyr. 3. but antagonized glycine responses in a concentration-dependent and surmountable manner. glycine receptor-mediated taurine responses were competitively antagonized by guanidinoethyl sulphonate. taurine dose-response curves, in contrast to the glycine dose-response curves were shifted by guanidinoethyl sulphonate to the right in a parallel manner [1]. | [in vivo]
guanidinoethyl sulphonate delivered in the drinking water of rats for 1 month could effectively reduce taurine levels in brain structures and outside the brain by between 50 and 80 %, depending on the tissue. this partial taurine depletion could not affect either basal synaptic transmission or the late phase of long-term potentiation in hippocampal slices. in-vivo microdialysis studies in the hippocampus demonstrated that guanidinoethyl sulphonate was able to reduce extracellular taurine levels and the magnitude of taurine released in response to the application of either n-methyl-d-aspartate or a hypoosmotic solution [2]. | [storage]
Store at -20°C | [References]
[1] sergeeva, o. a.,chepkova, a.n., and hass, h.l. guanidinoethyl sulphonate is a glycine receptor antagonist in striatum. british journal of pharmacology 137, 855-860 (2002).
[2] suárez lm, muoz md, gonzález jc, bustamante j, del río rm, solís jm. the taurine transporter substrate guanidinoethyl sulfonate mimics the action of taurine on long-term synaptic potentiation. amino acids. 2016 nov;48(11):2647-2656. epub 2016 jul 15. |
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