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SML2031 Sigma-Aldrich

S4

≥98% (HPLC)

Synonym: 4-(3′-(3″,5″-Dimethylphenyl)ureido)phenyl sulfamate, 4-[(3,5-Dimethylphenyl)ureido]phenyl sulfamate, 4-[[[(3,5-Dimethylphenyl)amino]carbonyl]amino]phenyl sulfamic acid ester

  • CAS Number 1330061-67-0

  • Empirical Formula (Hill Notation) C15H17N3O4S

  • Molecular Weight 335.38

  •  MDL number MFCD30182321

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, S
assay   ≥98% (HPLC)
form   powder
color   white to beige
solubility   DMSO: 2 mg/mL, clear
shipped in   ambient
storage temp.   2-8°C
SMILES string   O=S(OC1=CC=C(NC(NC2=CC(C)=CC(C)=C2)=O)C=C1)(N)=O

Description

Biochem/physiol Actions

S4 is a potent and selective inhibitor against sulfamate carbonic anhydrase (CA) subtypes CAIX & CAXII (Ki = 2, 7, 546, 5600 nM against human CA XII, IX, II, and I, respectively). S4 selectively inhibits migration upon anoxia/hypoxia-induced CAIX expression in cancer cultures (% inhibition/conc./cell line = 54%/100 μM/WRO, 65%/33 μM/MDA-MB-231), while exhibiting no inhibitory effects under normoxia or among non-CAIX-expressing cells (HCT116 & RT112). Daily intraperitoneal injection (10 mg/kg) is reported to reduce the metastatic tumor burden in lungs of mice bearing orthotopic eGFP-MDA-MB-231 tumors in vivo.

Safety & Documentation

Safety Information

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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