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R8279 Sigma-Aldrich

RG108

≥98% (HPLC), powder

Synonym: N-Phthalyl-L-tryptophan

  • CAS Number 48208-26-0

  • Empirical Formula (Hill Notation) C19H14N2O4

  • Molecular Weight 334.33

  •  PubChem Substance ID 24724594

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Bioactive Small Molecules for Epigenetic Research, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   yellow
solubility   DMSO: >10 mg/mL
storage temp.   −20°C
SMILES string   OC(=O)[C@H](Cc1c[nH]c2ccccc12)N3C(=O)C4=CCCC=C4C3=O
InChI   1S/C19H16N2O4/c22-17-13-6-1-2-7-14(13)18(23)21(17)16(19(24)25)9-11-10-20-15-8-4-3-5-12(11)15/h3-8,10,16,20H,1-2,9H2,(H,24,25)/t16-/m0/s1
InChI key   LMAZUAXDZRILNJ-INIZCTEOSA-N

Description

General description

RG108, a non-nucleoside analog is also called [2-(1,3-dioxoisoindolin-2-yl)-3-(1H-indol-3-yl) propanoic acid.

Application

RG108 has been used:
• in reprogramming and increasing cell plasticity of primary multipotent mesenchymal stromal cells (MMSC)
• as an inhibitor of DNA methyltransferase (DNMTi) in human retinal pigment epithelial ARPE-19 cells
• as a DNA methyltransferase inhibitor in C33A2 cells to test its effect on papillomavirus late gene expression (HPV16)

Packaging

10 mg in glass bottle

Biochem/physiol Actions

RG108 is a DNA methyltransferase (DMNT) inhibitor. It reactivates tumor suppressor gene expression (p16, SFRP1, secreted frizzled related protein-1, and TIMP-3) in tumor cells by DNA demethylation. RG108 also inhibits human tumor cell line (HCT116, NALM-6) proliferation and increased doubling time in culture.

RG108 is less cytotoxic compared to azacytidine (5-Aza-dCR). It mediates radiosensitivity in esophageal cancer cells (EC). RG108 is a potent epigenetic modulator and a demethylating agent. It elicits non-cytotoxic functionality and may be useful in stem cell therapies based on human bone marrow-derived mesenchymal stem cells (hBMSCs). It interacts with DNA methyltransferase 1 at the catalytic domain region.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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

Articles

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Modulators and Proteins for Methylation

DNA methyltransferases are a family of enzymes that catalyze the transfer of a methyl group to DNA. There are five related DNA cytosine-5-methyltransferases (DNMTs) that transfer a methyl group from ...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 7–9
Keywords: Gene expression, Methylations

Peer-Reviewed Papers
15

References

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