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SML2017 Sigma-Aldrich

Compound C108

≥98% (HPLC)

Synonym: 2-Hydroxy-2-[1-(2-hydroxyphenyl)ethylidene]hydrazide-benzoic acid, 2-Hydroxy-N′-[1-(2-hydroxyphenyl)ethylidene]benzohydrazide

  • CAS Number 15533-09-2

  • Empirical Formula (Hill Notation) C15H14N2O3

  • Molecular Weight 270.28

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, CI-CZ, Cell Biology
assay   ≥98% (HPLC)
form   powder
color   white to beige
solubility   DMSO: 2 mg/mL, clear
shipped in   ambient
storage temp.   −20°C
SMILES string   OC1=C(C=CC=C1)C(C)=NNC(C2=C(C=CC=C2)O)=O

Description

Biochem/physiol Actions

C108 is a small molecule that exhibits cancer-selective cytotoxicity (Viability = 100%/MCF-10A vs. 50%/BT-474, 67%/4T1, 70%/MDA-MB-231 & MDA-MB-453 post 48 h 1 μM C108 treatment) and synergizes with low dose paclitaxel in reducing ALDH-positive tumor-initiating cells (TIC poulation = 56.6%/control, 60.6%/0.1 μM paclitaxel alone, 47.4%/1 μM C108 alone, 7.3%/combined treatment for 24 h in BT474 breast cancer cultures) by targeting stress granule-associated protein G3BP2 (GAP SH3 domain-binding protein 2). Likewise, C108 pretreatment prior to xenografting greatly reduces BT-474 tumor-initiating frequency (from 1/175 to 1/1103 by limiting dilution xenograft assays) in mice in vivo. G3BP2 is reported to bind and stabilize SART3 mRNA, thereby indirectly regulating the core pluripotency transcription factors Oct-4 and Nanog critically involved in ESC self-renewal and breast tumor initiation.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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