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Merck

SML0778

Sigma-Aldrich

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
MDL number:
MFCD26960958
UNSPSC Code:
41121800
PubChem Substance ID:
329825598
NACRES:
NA.77

Key Documents

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Product Name

UNC1999, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

2-8°C

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
026M4774V
083M4628V

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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
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
Wei Li et al.
Cancer biology & medicine, 16(3), 530-541 (2019-10-01)
To explore the effect of dysregulation of epigenetic regulator EZH1 and EZH2 on the proliferation in MCL and the underlying mechanisms. In this study, we elucidated the role of EZH1 and EZH2 overexpression by immunohistochemistry and correlated them to clinical
Xiaoning Wu et al.
The Prostate, 79(10), 1079-1089 (2019-05-20)
Enhancer of zeste 2 (EZH2) promotes prostate cancer progression. We hypothesized that increased EZH2 expression is associated with postradiotherapy metastatic disease recurrence, and may promote radioresistance. EZH2 expression was investigated using immunohistochemistry in diagnostic prostate biopsies of 113 prostate cancer
Iva A Tchasovnikarova et al.
Molecular cell, 82(2), 479-491 (2021-12-29)
Genetically encoded biosensors are powerful tools to monitor cellular behavior, but the difficulty in generating appropriate reporters for chromatin factors hampers our ability to dissect epigenetic pathways. Here, we present TRACE (transgene reporters across chromatin environments), a high-throughput, genome-wide technique
View All Related Papers

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