SML1827

CCF642

≥98% (HPLC)

• Synonym(s): 3-(4-Methoxyphenyl)-5-((5-nitrothiophen-2-yl)methylene)-2-thioxothiazolidin-4-one
• Empirical Formula (Hill Notation): C₁₅H₁₀N₂O₄S₃
• CAS Number: 346640-08-2
• Molecular Weight: 378.45
• UNSPSC Code: 12352200
• PubChem Substance ID: 329826084
• NACRES: NA.77
• MDL number: MFCD01899742
• Assay: ≥98% (HPLC)
• Form: powder
• Storage condition: protect from light

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• storage condition: protect from light
• color: yellow to orange
• solubility: DMSO: 5 mg/mL, clear (warmed)
• storage temp.: 2-8°C
• SMILES string: S=C1SC(C(N1C(C=C2)=CC=C2OC)=O)=CC(S3)=CC=C3[N+]([O-])=O
• InChI: 1S/C15H10N2O4S3/c1-21-10-4-2-9(3-5-10)16-14(18)12(24-15(16)22)8-11-6-7-13(23-11)17(19)20/h2-8H,1H3
• InChI key: SPYIETQLOVDJCF-UHFFFAOYSA-N

Description

Application

CCF642 has been used as a protein disulfide isomerase (PDI) inhibitor to study its ability to reduce the expression of endoplasmic reticulum (ER) stress markers and neuroinflammation in the hippocampus of experimental autoimmune encephalomyelitis (EAE) mice.

Biochem/physiol Actions

CCF642 is a cell-permeable protein disulfide isomerase (PDI) inhibitor that exhibits 100-fold higher potency than PACMA 31 (by di-E-GSSG assay) via an alternative mode of action that most likely involves PDI active-site CGHCK motifs instead of cysteine known to be targeted by PACMA 31. CCF642 displays anti-multiple myeloma (MM) activity both in cultures in vitro (IC₅₀ <1 μM against murine 5TGM1 and nine human MM lines) and in mice in vivo (10 mg/kg, 3X i.p. per wk) without apparent adverse effects to the animals or being cytotoxic to normal bone marrow (NLBM) cells even at concentrations as high as 6.75 μM. Consistent with PDI′s role in ER protein folding process, CCF642 treatment causes acute ER stress accompanied by apoptosis-inducing calcium release in MM cells.

CCF642 is a cell-permeable protein disulfide isomerase (PDI) inhibitor.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3