SML1037

Sigma-Aldrich

UNC0642

≥98% (HPLC)

Synonym(s):
2-(4,4-Difluoropiperidin-1-yl)-6-methoxy-N-[1-(propan-2-yl)piperidin-4-yl]-7-[3-(pyrrolidin-1-yl)propoxy]quinazolin-4-amine
Empirical Formula (Hill Notation):
C29H44F2N6O2
Molecular Weight:
546.70
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

FC(CC1)(F)CCN1C2=NC(NC3CCN(C(C)C)CC3)=C4C(C=C(OCCCN5CCCC5)C(OC)=C4)=N2

InChI

1S/C29H44F2N6O2/c1-21(2)36-14-7-22(8-15-36)32-27-23-19-25(38-3)26(39-18-6-13-35-11-4-5-12-35)20-24(23)33-28(34-27)37-16-9-29(30,31)10-17-37/h19-22H,4-18H2,1-3H3,(H,32,33,34)

InChI key

RNAMYOYQYRYFQY-UHFFFAOYSA-N

Application

UNC0642 has been used to treat human HeLa cells to inhibit the DNA ligase 1 (LIG1) /UHRF1 (ubiquitin-like with PHD and ring finger domains 1) interaction.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

UNC0642 is a potent, selective inhibitor of histone methyltransferases G9a (EHMT2) and GLP (EHMT1), which catalyze the mono and dimethylation of lysine 9 of histone 3 (H3K9), and other non-histone substrates such as p53 and WIZ. UNC0642 has an in vitro IC50 <15 nM with greater than 100-fold selectivity over 13 other HMTs and selected representatives of kinases, ion channels, 7TMs, and other epigenetic proteins. UNC0642 has the same potency with improved PK properties relative to UNC0638, which should make it a more useful probe in an in vivo setting. For full characterization details, please visit the UNC0642 probe summary on the Structural Genomics Consortium (SGC) website.

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

Features and Benefits

UNC0642 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

UNC0642 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the UNC0642 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

Tiffani D M Berkel et al.
The international journal of neuropsychopharmacology, 22(4), 292-302 (2018-12-28)
Tolerance to ethanol-induced anxiolysis promotes alcohol intake, thus contributing to alcohol use disorder development. Recent studies implicate histone deacetylase-mediated histone H3K9 deacetylation in regulating neuropeptide Y expression during rapid ethanol tolerance to the anxiolytic effects of ethanol. Furthermore, the histone...
Yue-Peng Cao et al.
Acta pharmacologica Sinica, 40(8), 1076-1084 (2019-02-16)
Urinary bladder cancer (UBC) is characterized by frequent recurrence and metastasis despite the standard chemotherapy with gemcitabine and cisplatin combination. Histone modifiers are often dysregulated in cancer development, thus they can serve as an excellent drug targets for cancer therapy....
Methylation of DNA Ligase 1 by G9a/GLP Recruits UHRF1 to Replicating DNA and Regulates DNA Methylation.
Ferry L, et al.
Molecular Cell, 67(4), 550-565 (2017)
Chengfa Zhao et al.
Reproduction (Cambridge, England), 157(4), 359-369 (2019-02-08)
Somatic cell nuclear transfer in mammalian cloning suffers from a faulty epigenetic reprogramming, which is believed to cause developmental failures in cloned embryos. Regulating the epigenetic-modifying enzymes can rescue the chromatin of cloned embryos from aberrant epigenetic status, thereby potentially...
So Young Kim et al.
Chemico-biological interactions, 332, 109277-109277 (2020-10-03)
The unfolded protein response (UPR) is an emerging target pathway for cancer treatment owing to its ability to induce cell death. In our previous analysis of UPR-modulating small molecules, we had reported that piperazine oxalate derivative compounds (AMC-01-04) are able...
Related Content
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.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.