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C9873

Sigma-Aldrich

CPTH2

≥98% (HPLC), powder

Synonym(s):

Cyclopentylidene-[4-(4-chlorophenyl)thiazol-2-yl)hydrazone

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About This Item

Empirical Formula (Hill Notation):
C14H14ClN3S
CAS Number:
357649-93-5
Molecular Weight:
291.80
MDL number:
MFCD02307488
UNSPSC Code:
12352200
PubChem Substance ID:
329775211
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

Clc1ccc(cc1)-c2csc(N\N=C3\CCCC3)n2

InChI

1S/C14H14ClN3S/c15-11-7-5-10(6-8-11)13-9-19-14(16-13)18-17-12-3-1-2-4-12/h5-9H,1-4H2,(H,16,18)

InChI key

YYTHPXHGWSAKIZ-UHFFFAOYSA-N

General description

CPTH2 ((3-methylcyclopentylidene-[4-(4′-chlorophenyl)thiazol-2-yl]hydrazone)) inhibits histone acetyltransferase functionality and reduces acetylation of histone H3 and H4. CPTH2 promotes apoptosis in lymphoma cell lines. It may serve as an anticancer agent. CPTH2 inhibits α-tubulin acetylation and modulates autophagic pathway in human acute myeloid leukemia cell lines.

Application

CPTH2 has been used for the inhibition of histone acetyltransferase in cortical cultures, bud cells and natural killer T cells (iNKT).

Biochem/physiol Actions

CPTH2 is a histone acetyltransferase (HAT) inhibitor modulating the Gcn5 network. Histone Acetyltransferase (HAT) inhibitor modulating Gcn5 network. Histone acetyltransferases (HATs) act as transcriptional coactivators. Histone acetylation plays an important role in regulating the chromatin structure and is tightly regulated by two classes of enzyme, histone acetyltransferases (HAT) and histone deacetylases (HDAC). Deregulated HAT and HDAC activity plays a role in the development of a range of cancers. Consequently, inhibitors of these enzymes have potential as anticancer agents.

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.

Storage Class Code

11 - Combustible Solids

WGK

nwg

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 thiazole derivative CPTH6 impairs autophagy
Ragazzoni Y, et al.
Cell Death & Disease, 4(3), e524-e524 (2013)
The lysine acetyltransferase GCN5 is required for iNKT cell development through EGR2 acetylation
Wang Y, et al.
Cell Reports, 20(3), 600-612 (2017)
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4?-chlorophenyl) thiazol-2-yl) hydrazone
Chimenti F, et al.
Journal of Medicinal Chemistry, 52(2), 530-536 (2008)
Interactive histone acetylation and methylation in regulating transdifferentiation-related genes during tunicate budding and regeneration
Shibuya M, et al.
Developmental Dynamics, 244(1), 10-20 (2015)
CPTH6, a thiazole derivative, induces histone hypoacetylation and apoptosis in human leukemia cells
Trisciuoglio D, et al.
Clinical Cancer Research, 18(2), 475-486 (2012)
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Articles

Histone Modification and Chromatin Remodeling | Epigenetics

Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.

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