AA9
AA9 Basic information
- Product Name:
- AA9
- Synonyms:
-
- SRS11-92
- Benzoic acid, 4-(cyclohexylamino)-3-[(phenylmethyl)amino]-, ethyl ester
- HT-1080,FRDA,Friedreich,Inhibitor,cell death,ataxia,SRS-11-92,SRS1192,Ferroptosis,inhibit,SRS11 92,SRS11-92
- Ethyl 3-(benzylamino)-4-(cyclohexylamino)benzoate
- SRS11-92, 10 mM in DMSO
- CAS:
- 1467047-25-1
- MF:
- C22H28N2O2
- MW:
- 352.47
- Mol File:
- 1467047-25-1.mol
AA9 Chemical Properties
- Boiling point:
- 523.7±45.0 °C(Predicted)
- Density
- 1.152±0.06 g/cm3(Predicted)
- storage temp.
- 4°C, protect from light
- solubility
- DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:4): 0.2 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml
- form
- A crystalline solid
- pka
- 5.48±0.20(Predicted)
- color
- White to off-white
AA9 Usage And Synthesis
Uses
SRS11-92, a Ferrostatin-1 (Fer-1) analogue, is a potent ferroptosis inhibitor. SRS11-92 inhibits ferroptotic cell death induced by Erastin in HT-1080 human fibrosarcoma cells (EC50=6 nM)[1].
Definition
ChEBI: SRS11-92 is an ethyl ester resulting from the formal condensation of the carboxy group of 3-(benzylamino)-4-(cyclohexylamino)benzoic acid with ethanol. It is a potent inhibitor of ferroptosis induced by erastin in HT-1080 human fibrosarcoma cells (EC50 = 6 nM). It has a role as a ferroptosis inhibitor. It is a substituted aniline, an ethyl ester, a secondary amino compound and a diamine. It is functionally related to a ferrostatin-1.
Biological Activity
SRS11-92 is a cell penetrant and potent inhibitor of ferroptosis th at attenuates the cell death associated with frataxin knockdown in healthy human fibroblasts. SRS11-92 protects against cell death in in a brain slice model of Huntington′s disease, an oligodendrocyte model of periventricular leukomalacia, and in isolated kidney proximal tubules model of kidney disfunction.
in vivo
SRS11-92, used at 500 nM, is efficacious in protecting human and mouse cellular models of Friedreich ataxia (FRDA) treated with ferric ammonium citrate (FAC) and an inhibitor of glutathione synthesis (BSO), whereas caspase-3 inhibitors fail to show significant biological activity[2].
References
[1] Skouta R, et al. Ferrostatins inhibit oxidative lipid damage and cell death in diverse disease models. J Am Chem Soc. 2014;136(12):4551-4556. DOI:10.1021/ja411006a
[2] Cotticelli MG, et al. Ferroptosis as a Novel Therapeutic Target for Friedreich's Ataxia. J Pharmacol Exp Ther. 2019;369(1):47-54. DOI:10.1124/jpet.118.252759
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