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SML1751

Sigma-Aldrich

GSK591

≥97% (HPLC)

Synonym(s):

2-(Cyclobutylamino)-N-[(2S)-3-(3,4-dihydro-2(1H)-isoquinolinyl)-2-hydroxypropyl]-4-pyridinecarboxamide., EPZ015866, GSK 591, GSK3203591

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About This Item

Empirical Formula (Hill Notation):
C22H28N4O2
CAS Number:
1616391-87-7
Molecular Weight:
380.48
MDL number:
MFCD30187524
UNSPSC Code:
12352200
PubChem Substance ID:
329826054
NACRES:
NA.77

Quality Level

100

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

Biochem/physiol Actions

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
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).

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.
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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Kazuki Fukumoto et al.
Communications biology, 5(1), 313-313 (2022-04-07)
The global dietary supplement market is valued at over USD 100 billion. One popular dietary supplement, S-adenosylmethionine, is marketed to improve joints, liver health and emotional well-being in the US since 1999, and has been a prescription drug in Europe
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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