SML1751

Sigma-Aldrich

GSK591

≥97% (HPLC)

Synonym(s):
GSK3203591, GSK 591, 2-(Cyclobutylamino)-N-[(2S)-3-(3,4-dihydro-2(1H)-isoquinolinyl)-2-hydroxypropyl]-4-pyridinecarboxamide., EPZ015866
Empirical Formula (Hill Notation):
C22H28N4O2
CAS Number:
Molecular Weight:
380.48
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(NC[C@H](O)CN1CCC(C=CC=C2)=C2C1)C3=CC=NC(NC4CCC4)=C3

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

GSK591 is also known as 2-(cyclobutylamino)-N-[(2S)-3-(3,4-dihydro-2(1H)-isoquinolinyl)-2-hydroxypropyl]-4-pyridinecarboxamide, EPZ015866 and GSK3203591. It prevents the systemic arginine methylation of SmD3 (small nuclear ribonucleoprotein).
GSK591 is a SGC probe for PRMT5. GSK591 is a potent and selective inhibitor of H4 histone methylation by PRMT5/MEP50 complex. For full characterization details, please visit the GSK591 probe summary on the Structural Genomics Consortium (SGC) website.

SGC2096 is the negative control for the active probe, GSK-591. To request a sample of the negative control from the SGC,
click here.

To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc

Features and Benefits

GSK591 is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit sigma.com/SGC.

Other Notes

GSK591 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the GSK591 probe summary on the Chemical Probes Portal website.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

The Inhibitor Index: A Desk Reference on Enzyme Inhibitors, Receptor Antagonists, Drugs, Toxins, Poisons, Biologics, and Therapeutic Leads, 1362-1362 (2017)
Juan Dong et al.
Nature communications, 10(1), 4705-4705 (2019-10-19)
DNA methylation, repressive histone marks, and PIWI-interacting RNA (piRNA) are essential for the control of retrotransposon silencing in the mammalian germline. However, it remains unknown how these repressive epigenetic pathways crosstalk to ensure retrotransposon silencing in the male germline. Here...
Coralie Poulard et al.
Methods (San Diego, Calif.), 175, 66-71 (2019-09-10)
Arginine methylation is now recognized as a major contributor to proteome diversity and is, as such, involved in a large range of cellular processes. There is a growing need for assessing endogenous protein arginine methylation in cells. Besides the classical...
Carolin Dorothea Strobl et al.
Molecular cancer therapeutics, 19(2), 409-419 (2019-11-13)
Genetic alterations in tumor cells provide promising targets for antitumor therapy. Recently, loss of methylthioadenosine phosphorylase (MTAP), a deletion frequently occurring in cancer, has been shown to create vulnerability to the inhibition of the protein arginine methyltransferase 5 (PRMT5). MTAP...
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