| Identification | Back Directory | [Name]
(S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxaMide | [CAS]
848193-72-6 | [Synonyms]
CHIC-35
Compound (S)-35
SIRT1 Inhibitor IV, (S)-35
SIRT1 Inhibitor IV, (S)-35 - CAS 848193-72-6 - Calbiochem
(S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxaMide
(6S)-2-Chloro-5,6,7,8,9,10-hexahydro-cyclohept[b]indole-6-carboxamide
Cyclohept[b]indole-6-carboxamide, 2-chloro-5,6,7,8,9,10-hexahydro-, (6S)- | [Molecular Formula]
C14H15ClN2O | [MDL Number]
MFCD11045286 | [MOL File]
848193-72-6.mol | [Molecular Weight]
262.73 |
| Hazard Information | Back Directory | [Uses]
CHIC35, an analog of EX-527, is a potent and selective inhibitor of SIRT1 (IC50=0.124 μM). CHIC35 shows potential selective inhibition against SIRT1 over SIRT2 (IC50=2.8 μM) or SIRT3 (IC50>100 μM)[1]. CHIC35 has anti-inflammatory effects and can be used for CHARGE syndrome research[1][2]. | [Definition]
ChEBI: CHIC-35 is an organic heterotricyclic compound resulting from the formal fusion of the 2-3 bond of 5-chloroindole with the 2-3 bond of cycloheptanecarboxamide (the S enantiomer). It is a potent, cell-permeable, metabolically stable and selective inhibitor of the deacetylase SIRT1. It has a role as an EC 3.5.1.98 (histone deacetylase) inhibitor. It is an aromatic compound, an organic heterotricyclic compound, an organochlorine compound and a primary carboxamide. | [General Description]
A cell-permeable entiomerically pure compound that is structurally similar to and exhibits similar potency (IC50 = 63 nM) and selectivity as SIRT1 Inhibitor III (Cat. No. 566322). Shown to be orally bioavailable with a serum half-life of 94 minutes in mice in vivo. | [Biochem/physiol Actions]
CHIC-35 is cell-permeable, metabolically stable, and very potent inhibitor of SIRT1; IC50 of S-isomer is 60 nM; IC50 of mixed isomers is 124 nM. There is no inhibition of SIRT3 or HDAC. The IC50 for SIRT2 is 2.77 μM. Sirtuins are protein deacetylases, which represent a new class of histone deacetylases (HDAC) involved in gene silencing. SIRT modulators are potential therapeutics for cancer, diabetes, muscle differentiation, heart failure, neurodegeneration, and aging. | [IC 50]
SIRT1: 0.124 μM (IC50); SIRT2: 2.8 μM (IC50); SIRT3: >100 μM (IC50) | [storage]
Store at -20°C | [References]
[1] Jér?me Lugrin, et al. The sirtuin inhibitor cambinol impairs MAPK signaling, inhibits inflammatory and innate immune responses and protects from septic shock. Biochim Biophys Acta. 2013 Jun;1833(6):1498-510 DOI:10.1016/j.bbamcr.2013.03.004
[2] Zainab Asad, et al. Chemical screens in a zebrafish model of CHARGE syndrome identifies small molecules that ameliorate disease-like phenotypes in embryo. Eur J Med Genet. 2020 Feb;63(2):103661. DOI:10.1016/j.ejmg.2019.04.018 |
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