Description
Aminoethyl-SS-ethylamine contains two primary amine terminal groups and a cleavable disulfide bond. The terminal amines can participate in chemical reactions with carboxylic acids, activated NHS esters and other carbonyl compounds. The disulfide bond can be cleaved by Dithiothreitol (DTT) reagent.
Chemical Properties
Cystamine is an unstable liquid, and its dihydrochloride C4H12N2S2·2HCl is generally used. The latter is stable to 203-214°C and decomposes above this temperature.
Uses
Cystamine is the disulfide form of the free thiol, cysteamine. Cystamine is an orally active transglutaminase (Tgase) inhibitor. Cystamine also has inhibition activity for caspase-3 with an IC50 value of 23.6 μM. Cystamine can be used for the research of severals diseases including Huntington's disease (HD) [1][2][3].
Definition
ChEBI: An organic disulfide obtgained by oxidative dimerisation of cysteamine.
Synthesis
Cystamine is an organic disulfide that can be formed from the thermal decarboxylation of cystine.
in vivo
Cystamine (oral, i.p.; 112, 225 mg/kg) reduces Tgase activity and GGEL levels, lessens the behavioral and neuropathological severity, and extends survival in R6/2 transgenic HD mice[2].
| Animal Model: | R6/2 transgenic HD mice[2] |
| Dosage: | 112, 225 mg/kg |
| Administration: | Intraperitoneal or oral, daily |
| Result: | Significantly extended survival, improved body weight and motor performance, delayed the neuropathological sequela and significantly altered the levels of Tgase activity and N(Sigma)-(gamma-L-glutamyl)-L-lysine (GGEL) levels. |
IC 50
Caspase 3: 23.6 μM (IC
50)
References
[1] Mathieu Lesort, et al. Cystamine inhibits caspase activity. Implications for the treatment of polyglutamine disorders. J Biol Chem. 2003 Feb 7;278(6):3825-30. DOI:
10.1074/jbc.M205812200[2] Alpaslan Dedeoglu, et al. Therapeutic effects of cystamine in a murine model of Huntington's disease. J Neurosci. 2002 Oct 15;22(20):8942-50. DOI:
10.1523/JNEUROSCI.22-20-08942.2002[3] Thomas M Jeitner, et al. Cystamine and cysteamine as inhibitors of transglutaminase activity in vivo. Biosci Rep. 2018 Sep 5;38(5):BSR20180691. DOI:
10.1042/BSR20180691
