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R8279

Sigma-Aldrich

RG108

≥98% (HPLC), powder

Synonyme(s) :

N-Phthalyl-L-tryptophan

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About This Item

Formule empirique (notation de Hill):
C19H14N2O4
Numéro CAS:
48208-26-0
Poids moléculaire :
334.33
Code UNSPSC :
12352200
ID de substance PubChem :
24724594
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

[α]/D -250 to -310°, c = 0.5 in methanol

Couleur

yellow

Solubilité

DMSO: >10 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

LMAZUAXDZRILNJ-INIZCTEOSA-N

Description générale

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)

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Lucia Bialesova et al.
Scientific reports, 7(1), 10152-10152 (2017-09-02)
Increased adipocyte lipolysis links obesity to insulin resistance. The lipid droplet coating-protein Perilipin participates in regulation of lipolysis and is implicated in obesity. In the present study we investigate epigenetic regulation of the PLIN1 gene by correlating PLIN1 CpG methylation
Cecilia Johansson et al.
Virology, 482, 244-259 (2015-04-23)
We report that many histone modifications are unevenly distributed over the HPV16 genome in cervical cancer cells as well as in HPV16-immortalized keratinocytes. For example, H3K36me3 and H3K9Ac that are common in highly expressed cellular genes and over exons, were
German Todorov et al.
Scientific reports, 9(1), 8741-8741 (2019-06-21)
Mental health disorders are manifested in families, yet cannot be fully explained by classical Mendelian genetics. Changes in gene expression via epigenetics present a plausible mechanism. Anxiety often leads to avoidant behaviors which upon repetition may become habitual, maladaptive and
Peter Karagiannis et al.
Physiological reviews, 99(1), 79-114 (2018-10-18)
The discovery of somatic cell nuclear transfer proved that somatic cells can carry the same genetic code as the zygote, and that activating parts of this code are sufficient to reprogram the cell to an early developmental state. The discovery
Yao Ou et al.
Oncology reports, 39(3), 993-1002 (2018-01-13)
Esophageal cancer (EC) is the eighth most common highly aggressive cancer worldwide. The purpose of this study was to investigate the effect of the DNA methyltransferase inhibitor RG108 on the radiosensitivity of EC cells. MTT and clonogenic assays were performed
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Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

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