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Merck

SML0778

UNC1999

≥98% (HPLC), EZH2 and EZH1 lysine methyltransferases inhibitor, powder

Synonym(s):

1-Isopropyl-6-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C33H43N7O2
CAS Number:
1431612-23-5
Molecular Weight:
569.74
UNSPSC Code:
41121800
PubChem Substance ID:
329825598
NACRES:
NA.77
MDL number:
MFCD26960958
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

UNC1999, ≥98% (HPLC)

SMILES string

CC(C)N1CCN(C2=NC=C(C3=CC4=C(C=NN4C(C)C)C(C(NCC5=C(CCC)C=C(C)NC5=O)=O)=C3)C=C2)CC1

InChI

1S/C33H43N7O2/c1-7-8-24-15-23(6)37-33(42)28(24)19-35-32(41)27-16-26(17-30-29(27)20-36-40(30)22(4)5)25-9-10-31(34-18-25)39-13-11-38(12-14-39)21(2)3/h9-10,15-18,20-22H,7-8,11-14,19H2,1-6H3,(H,35,41)(H,37,42)

InChI key

DPJNKUOXBZSZAI-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

The polycomb repressive complex 2 (PRC2), which represses gene expression through methylation of histone H3 on lysine 27 (H3K27), contains either EZH1 or EZH2 as its catalytic subunit, with EZH1 being found in both dividing and non-dividing cells, whereas EZH2 is only found in actively dividing cells. UNC1999 is an orally bioavaliable selective inhibitor of both EZH2 and EZH1 lysine methyltransferases with IC50 < 10 nM for EZH2 and 45 nM for EZH1. UNC1999 potently inhibited both wild-type and mutant Y641N EZH2 methyltransferase activity with less than a 5-fold difference in potency, and selectively killed diffused large B cell lymphoma (DLBCL) cells bearing Y641 point mutations. It was selective for EZH2 and EZH1 over 15 other lysine, arginine and DNA methyltransferases. UNC1999 is competitive with the cofactor S-adenosylmethionine (SAM) and non-competitive with the peptide substrate. Because it inhibits both EZH2 and EZH1, UNC1999 has potential advantages over EZH2 selective inhibitors in the disease settings where both PRC2 – EZH2 and PRC2 – EZH1 contribute to the methylation of H3K27.

For full characterization details, please visit the UNC1999 probe summary on the Structural Genomics Consortium (SGC) website.

UNC2400 is the negative control for the active probe, UNC1999. 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
UNC1999 is an orally bioavailable selective inhibitor of both EZH2 and EZH1 lysine methyltransferases.

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.
UNC1999 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

UNC1999 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the UNC1999 probe summary on the Chemical Probes Portal website.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

SML0778-5MG: + SML0778-VAR: + SML0778-BULK: + SML0778-25MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000502946
0000502945
0000502946
0000502945
0000242233

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Kyunghwan Kim et al.
Epigenetics & chromatin, 11(1), 23-23 (2018-05-29)
MMP-9 plays a direct role in the activation of pro-osteoclastogenic genes by cleaving histone H3N-terminal tail (H3NT) and altering chromatin architecture. Although H3 acetylation at K18 has been shown to stimulate MMP-9 enzymatic activity toward H3NT, nothing is known about
Chen Hou et al.
Frontiers in genetics, 13, 1013475-1013475 (2022-10-25)
Although gene mutations and aberrant chromosomes are associated with the pathogenesis and prognosis of uveal melanoma (UM), potential therapeutic targets still need to be explored. We aim to determine the predictive value and potential therapeutic target of EZH2 in uveal
Peter E Feist et al.
Analytical chemistry, 89(5), 2773-2781 (2017-02-15)
Multicellular tumor spheroids (MCTS) are valuable in vitro tumor models frequently used to evaluate the penetration and efficacy of therapeutics. In this study, we evaluated potential differences in epigenetic markers, i.e., histone post-translational modifications (PTMs), in the layers of the
Geneviève Deblois et al.
Cancer discovery, 10(9), 1312-1329 (2020-06-18)
Tumor progression upon treatment arises from preexisting resistant cancer cells and/or adaptation of persister cancer cells committing to an expansion phase. Here, we show that evasion from viral mimicry response allows the growth of taxane-resistant triple-negative breast cancer (TNBC). This
Christiaan J Stavast et al.
Leukemia (2021-11-07)
MIR139 is a tumor suppressor and is commonly silenced in acute myeloid leukemia (AML). However, the tumor-suppressing activities of miR-139 and molecular mechanisms of MIR139-silencing remain largely unknown. Here, we studied the poorly prognostic MLL-AF9 fusion protein-expressing AML. We show
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