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SML1356

Sigma-Aldrich

Sephin1

≥95% (HPLC)

Synonym(s):

(E)-2-(2-Chlorobenzylidene)hydrazinecarboximidamide, Sephin 1

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About This Item

Empirical Formula (Hill Notation):
C8H9ClN4
CAS Number:
951441-04-6
Molecular Weight:
196.64
MDL number:
MFCD00790608
UNSPSC Code:
12352200
PubChem Substance ID:
329825811
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

NC(N/N=C/C1=CC=CC=C1Cl)=N

InChI

1S/C8H9ClN4/c9-7-4-2-1-3-6(7)5-12-13-8(10)11/h1-5H,(H4,10,11,13)/b12-5+

InChI key

PDWJALXSRRSUHR-LFYBBSHMSA-N

Biochem/physiol Actions

In vivo studies using mice models show that sephin1 suppresses neurodegeneration, by preventing eIF2α (eukaryotic initiation factor 2) dephosphorylation.
Sephin1 is a selective inhibitor of a holophosphatase. It is a guanabez derivative that binds to and inhibits a regulatory subunit of the stress-induced protein phosphatase 1 (PPP1R15A), but not the constitutive PPP1R15B, and lacks α2-adrenergic activity. Phosphorylation of eIF2α, α subunit of eukaryotic translation initiation factor 2, reduces protein synthesis and prevents the accumulation of misfolded protein in the endoplasmic reticulum (ER). PPP1R15A recruits the serine/threonine-protein phosphatase PP1 to dephosphorylate eIF2α, so inhibiting PPP1R15A activity prolongs the phosphorylation of eIF2α and aids in its prevention of the accumulation of misfolded protein. In vitro Sephin1 protected cells from lethal protein misfolding and cytotoxic ER stress. In vivo sephin1 prevented two unrelated protein misfolding diseases in mice (Charchot-Marie-Tooth 1B and ALS).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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PPP1R15A-mediated dephosphorylation of eIF2α is unaffected by Sephin1 or Guanabenz.
Crespillo-Casado A, et al.
eLife, 6, e26109-e26109 (2017)
Nadejda Capatina et al.
The Journal of physiology, 599(17), 4153-4181 (2021-07-17)
Endoplasmic reticulum (ER) stress promotes placental dysmorphogenesis and is associated with poor pregnancy outcomes. We show that unfolded protein response signalling pathways located in the ER drive differentiation of mouse trophoblast stem cells into trophoblast subtypes involved in development of

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