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SML1358 Sigma-Aldrich

SGI-1027

≥98% (HPLC)

Synonym: N-(4-(2-Amino-6-methylpyrimidin-4-ylamino)phenyl)-4-(quinolin-4-ylamino) benzamide

  • CAS Number 1020149-73-8

  • Empirical Formula (Hill Notation) C27H23N7O

  • Molecular Weight 461.52

  •  MDL number MFCD27937047

  •  PubChem Substance ID 329825813

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, DNA-RNA Transcription Regulators,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   white to light brown
solubility   DMSO: 20 mg/mL, clear
storage temp.   2-8°C
SMILES string   O=C(NC1=CC=C(NC2=NC(N)=NC(C)=C2)C=C1)C(C=C3)=CC=C3NC4=C(C=CC=C5)C5=NC=C4
InChI   1S/C27H23N7O/c1-17-16-25(34-27(28)30-17)32-20-10-12-21(13-11-20)33-26(35)18-6-8-19(9-7-18)31-24-14-15-29-23-5-3-2-4-22(23)24/h2-16H,1H3,(H,29,31)(H,33,35)(H3,28,30,32,34)
InChI key   QSYLKMKIVWJAAK-UHFFFAOYSA-N

Description

Application

SGI-1027 has been used as a DNA methyltransferase inhibitor to study its effects on gene expression during osteogenic differentiation. It has also been used as a DNA methyltransferase 3a inhibitor to study its effects on interleukin-6 (IL-6)-induced loss of forkhead box P3 (Foxp3) gene expression in B-lymphocyte-induced maturation protein 1 (Blimp1)-Treg cells.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

SGI-1027 is a DNA methyltransferase (DNMT) inhibitor with IC50 values of 6-13 μM for DNMT3B, DNMT3A and DNMT1. SGI-1027 directly inhibits DNMT activity by competing with the cofactor, S-adenosylmethionine (SAM) in the methylation reaction. SGI-1027 treatment of cancer cell lines induced degradation of DNMT1, but not DNMT3A or DNMT3B, and in RKO cells caused re-expression of the silenced tumor supressor genes p16, MLH1 and TIMP3.

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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