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O3139

Sigma-Aldrich

Oxamflatin

≥98% (HPLC), solid

Synonym(s):

(2E)-5-[3-(Phenylsulfonylamino)phenyl]-pent-2-en-4-ynohydroxamic acid

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About This Item

Empirical Formula (Hill Notation):
C17H14N2O4S
CAS Number:
151720-43-3
Molecular Weight:
342.37
MDL number:
MFCD00949087
UNSPSC Code:
12352203
PubChem Substance ID:
329818905
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

solubility

DMSO: soluble 13 mg/mL

storage temp.

2-8°C

SMILES string

ONC(=O)\C=C\C#Cc1cccc(NS(=O)(=O)c2ccccc2)c1

InChI

1S/C17H14N2O4S/c20-17(18-21)12-5-4-7-14-8-6-9-15(13-14)19-24(22,23)16-10-2-1-3-11-16/h1-3,5-6,8-13,19,21H,(H,18,20)/b12-5+

InChI key

QRPSQQUYPMFERG-LFYBBSHMSA-N

Application

Oxamflatin has been used as a histone deacetylase (HDAC) inhibitor:
  • to study its effect on specificity protein 1 (Sp1) transcription and transactivation activity and CD1d mRNA expression in various tumor cells
  • to study its inhibitory effect on long transcript- survival motor neuron gene 2 (SMN2) silencing mediated by DNA methylation
  • to study its effect on somatic embryogenesis in Coffea arabica thorough a miniaturized and automated screening system
  • to study its stand-alone effect on cytarabine-sensitive and resistant cells.

Biochem/physiol Actions

Oxamflatin is an aromatic sulfonamide derivative with a hydroxamic acid group. It stimulates the expression of the transcription factor, JunD, and fibronectin. In addition, oxamflatin also aids in the morphological reversion of various NIH3T3-derived transformed cell lines. It inhibits the proliferation of various mouse and human tumor cell lines in vitro.
Histone deacetylase inhibitor; anti-cancer agent.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Oxamflatin is a novel antitumor compound that inhibits mammalian histone deacetylase.
Kim, et al.
Oncogene, 18, 2461-2470 (2012)
Jan Hauke et al.
Human molecular genetics, 18(2), 304-317 (2008-10-31)
Spinal muscular atrophy (SMA), a common neuromuscular disorder, is caused by homozygous absence of the survival motor neuron gene 1 (SMN1), while the disease severity is mainly influenced by the number of SMN2 gene copies. This correlation is not absolute
Rayan Awada et al.
Scientific reports, 10(1), 810-810 (2020-01-23)
Somatic embryogenesis (SE) faces many challenges in fulfilling the growing demand for elite materials. A high-throughput approach is required to accelerate the optimization of SE protocols by multiplying experimental conditions within a limited time period. For the first time in
Pei-Ming Yang et al.
Epigenetics, 7(4), 390-399 (2012-03-16)
CD1d is a MHC class-like molecule that presents glycolipids to natural killer T (NKT) cells, then regulates innate and adaptive immunity. The regulation of CD1d gene expression in solid tumors is still largely unknown. Gene expression can be epigenetically regulated
Catja Freiburghaus et al.
BMC cancer, 18(1), 466-466 (2018-04-27)
The addition of high-dose cytarabine to the treatment of mantle cell lymphoma (MCL) has significantly prolonged survival of patients, but relapses are common and are normally associated with increased resistance. To elucidate the mechanisms responsible for cytarabine resistance, and to

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

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.

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