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SML1037

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

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About This Item

Empirical Formula (Hill Notation):
C29H44F2N6O2
CAS Number:
1481677-78-4
Molecular Weight:
546.70
NACRES:
NA.77
PubChem Substance ID:
329825635
UNSPSC Code:
51111800
MDL number:
MFCD28044322
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Quality Level

100

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

Related Categories

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.

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
UNC0642 is a potent, selective inhibitor of histone methyltransferases; G9a and GLP selective methhylransferase chemical probe.

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.
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.

Storage Class

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
0000162557
0000162558
0000162557
0000102951

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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.
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
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)
Patricia D B Tiburcio et al.
Translational oncology, 13(10), 100819-100819 (2020-07-06)
Malignant gliomas have disproportionally high morbidity and mortality. Heterozygous mutations in the isocitrate dehydrogenase 1 (IDH1) gene are most common in glioma, resulting in predominantly arginine to histidine substitution at codon 132. Because IDH1R132H requires a wild-type allele to produce
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
View All Related Papers

Articles

Discover Bioactive Small Molecules for Gene Regulation

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.

Global Trade Item Number

SKUGTIN
SML1037-5MG04061832635781
SML1037-25MG04061832635774

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