543-18-0 Usage
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 is a white solid and exists in a zwitterionic form at pH 7.3, arising from the transfer of a proton from the sulfo group to the guanidino group.
Uses
1. Used in Pharmaceutical Applications:
Guanidinoethyl sulfonate is used as a potent inhibitor of taurine transport for its ability to competitively inhibit taurine uptake by sodium-dependent taurine transporters in rat hepatocytes (Ki = 1.75 mM). This property makes it a valuable compound in the study and treatment of various conditions related to taurine transport.
2. Used in Neurological Applications:
Guanidinoethyl sulfonate is used as a competitive glycine receptor antagonist in mouse striatal neurons. This application highlights its potential role in the study and treatment of neurological disorders involving the glycine receptor.
3. Used in Chronic Renal Failure Research:
Plasma levels of guanidinoethyl sulfonate are significantly increased in patients with chronic renal failure. This makes it a potential biomarker or therapeutic target for further research and development in the treatment of 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].
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.
Check Digit Verification of cas no
The CAS Registry Mumber 543-18-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 3 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 543-18:
(5*5)+(4*4)+(3*3)+(2*1)+(1*8)=60
60 % 10 = 0
So 543-18-0 is a valid CAS Registry Number.
InChI:InChI=1/C3H9N3O3S/c4-3(5)6-1-2-10(7,8)9/h1-2H2,(H4,4,5,6)(H,7,8,9)
543-18-0Relevant articles and documents
ORGANIC DISULFIDES AND RELATED SUBSTANCES. IX. SYMMETRICAL
FIELD,FERRETTI,CRENSHAW,OWEN
, p. 39 - 44 (1964)
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ACIDES α ET β AMIDINO SULFONIQUES
Garrigues, Bernard,Lopez, Lucien,Mulliez, Michel
, p. 195 - 202 (2007/10/02)
The titel compounds (4 or 11, Table) are synthesized by coupling, in an aqueous basic medium, of the α or β amino sulfonic acids with thioiminoethers salts or cyanamide ( Fig. 4). Key words: thioiminoethers; cyclization in aqueous medium; sulfonopeptides;