| Identification | Back Directory | [Name]
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE | [CAS]
49843-98-3 | [Synonyms]
CS-1862
(S)-EX-527
Selisistat
SEN0014196
EX 527, >=98%
EX 527; EX527
EX 527 (Selisistat)
EX 527 (SEN0014196)
SIRT1 Inhibitor III
Selisistat - EX 527
Selisistat (SEN0014196
SELISISTAT;EX 527;EX527;SEN0014196
EX-527; EX-527; EX-527; SELISISTAT.
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE
1H-Carbazole-1-carboxamide, 6-chloro-2,3,4,9-tetrahydro-
6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide >
(S)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE, >95%
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE USP/EP/BP
Selisistat 6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxaMide
6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide EX-527 Selisistat | [Molecular Formula]
C13H13ClN2O | [MDL Number]
MFCD03009471 | [MOL File]
49843-98-3.mol | [Molecular Weight]
248.71 |
| Chemical Properties | Back Directory | [Melting point ]
179.0 to 183.0 °C | [Boiling point ]
531.7±38.0 °C(Predicted) | [density ]
1.388 | [storage temp. ]
Store at +4°C | [solubility ]
Soluble in dimethyl sulfoxide, ethanol and dimethyl formamide. | [form ]
powder | [pka]
16.12±0.40(Predicted) | [color ]
white to beige | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months |
| Hazard Information | Back Directory | [Description]
EX-527 (49843-98-3) is a selective SIRT1 inhibitor (IC50=98 nM). Does not inhibit other HDACs or SIRT family members. Increases p53 acetylation following DNA damage. Cell permeable. | [Uses]
A selective inhibitor of SIRT1 over SIRT2 and SIRT3 | [Definition]
ChEBI: 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide is a member of the class of carbazoles that is 2,3,4,9-tetrahydro-1H-carbazole which is substituted at position 1 by an aminocarbohyl group and at position 6 by a chlorine. It is a member of carbazoles, a monocarboxylic acid amide and an organochlorine compound. | [General Description]
A cell-permeable indole compound that acts as a potent and highly selective inhibitor of SIRT1 (IC50 = 98 nM). It inhibits other sirtuin family deacetylases only at much higher concentrations (IC50 = 19.6 and 48.7 μM for SIRT2 and SIRT3, respectively) and shows no inhibitory effect against class I and II HDACs or NAD glycohydrolase even at concentrations as high as 100 μM. Shown to be orally bioavailable with a serum half-life of 136 minutes in mice in vivo. | [Biological Activity]
Selective inhibitor of SIRT1 that does not inhibit histone deacetylase (HDAC) or other sirtuin deacetylase family members (IC 50 values are 98, 19600, 48700, > 100000 and > 100000 nM for SIRT1, SIRT2, SIRT3, HDAC and NADase respectively). Enhances p53 acetylation in response to DNA damaging agents. | [Biochem/physiol Actions]
Primary TargetSIRT1 | [storage]
Store at +4°C | [References]
1) Napper et al. (2005), Discovery of indoles as potent and selective inhibitors of the deacetylase SIRT1; J. Med. Chem., 48 8045
2) Solomon et al. (2006) Inhibition of SIRT1 catalytic activity increases p53 acetylation but does not alter cell survival following DNA damage; Mol. Cell, 26 28
3) Gertz et al. (2013) EX-527 inhibits Sirtuins by exploiting their unique NAD+-dependent deacetylation mechanism; Proc. Natl. Acad. Sci. USA, 110 e2772 |
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