| Identification | Back Directory | [Name]
2-GUANIDINOETHYLMERCAPTOSUCCINIC ACID | [CAS]
77482-44-1 | [Synonyms]
GEMSA
2-Guanidinoethylthiosuccinic acid
GUANIDINOETHYLMERCAPTO-SUCCINIC ACID
2-GUANIDINOETHYLMERCAPTOSUCCINIC ACID
2-(2-Guanidinoethylthio)succinic acid
2-[(2-Guanidinoethyl)thio]succinic acid
(2-GUANIDINOETHYLMERCAPTO)SUCCINIC ACID 99+%
(2-Guanidinoethylthio)succinic acid, GEMSA
2-[(2-carbaMiMidaMidoethyl)sulfanyl]succinicacid
Butanedioic acid, 2-[[2-[(aminoiminomethyl)amino]ethyl]thio]-
2-Guanidinoethylmercaptosuccinic Acid - CAS 77482-44-1 - Calbiochem | [Molecular Formula]
C7H13N3O4S | [MDL Number]
MFCD00036862 | [MOL File]
77482-44-1.mol | [Molecular Weight]
235.26 |
| Chemical Properties | Back Directory | [Melting point ]
~180 °C (dec.) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO | [form ]
White solid | [color ]
white | [Water Solubility ]
water: soluble | [InChI]
1S/C7H13N3O4S/c8-7(9)10-1-2-15-4(6(13)14)3-5(11)12/h4H,1-3H2,(H,11,12)(H,13,14)(H4,8,9,10) | [InChIKey]
VKVCLXDFOQQABP-UHFFFAOYSA-N | [SMILES]
S(C(CC(=O)O)C(=O)O)CCN=C(N)N |
| Hazard Information | Back Directory | [Uses]
GEMSA is a potent inhibitor of enkephalin convertase (Ki=8.8 nM). GEMSA elicites analgesia[1]. | [Biological Activity]
ki: 8.8 nm2-guanidinoethylmercaptosuccinic acid is a carboxypeptidase e inhibitor.carboxypeptidase e, also known as enkephalin convertase, can remove c-terminal residues during the processing of propeptides, such as enkephalin and proinsulin. | [in vitro]
2-guanidinoethylmercaptosuccinic acid was identified as a biproduct analogs of lysine and arginine that showed potent inhibitory effect on enkephalin convertase with the ki value of 8.8 nm. in addition, 2-guanidinoethylmercaptosuccinic acid was found to be several hundred fold more potent towards enkephalin convertase than towards carboxypeptidase b or n and the kinetic analyses indicated the pure competitive nature of the inhibition [1]. | [in vivo]
previous study found that following the intrathecal administration of 2-guanidinoethylmercaptosuccinic acid at 12.5, 25 and 50 micrograms, an increase in the tail-flick latency was seen. in addition, 2-guanidinoethylmercaptosuccinic acid could potentiate the analgesic effects of the intrathecally applied met5-enkephalin-arg6-phe7 and met5-enkephalin-arg6-gly7-leu8. all these effects of 2-guanidinoethylmercaptosuccinic acid were significantly attenuated by the treatment of naloxone. moreover, the rats subjected to chronic pain showed a weaker analgesic response to the treatment of 2-guanidinoethylmercaptosuccinic acid. furthermore, 2-guanidinoethylmercaptosuccinic acid bound to enkephalin convertase in the spinal cord of these rats produced only a slight increase in kd [2]. | [storage]
Store at 4°C | [References]
1. fricker ld, plummer th jr, snyder sh. enkephalin convertase: potent, selective, and irreversible inhibitors. biochem biophys res commun. 1983 mar 29;111(3):994-1000.2. m. bommer, k. nikolarakis, e. p. noble, et al. in vivo modulation of rat hypothalamic opioid peptide content by intracerebroventricular injection of guanidinoethylmercaptosuccinic acid (gemsa): possible physiological role of enkephalin convertase. brain research 492(1-2), 305-313 (1989). |
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