Merck
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安全信息

T2580

Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

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别名:
Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl), RF 1023A
经验公式（希尔记法）:
C34H42N4O6
CAS号:
133155-89-2
分子量:
602.72
NACRES:
NA.77

生物来源

Helicoma ambiens

质量水平

200

检测方案

≥98% (HPLC)

形式

solid

溶解性

DMSO: soluble 0.9-1.10 mg/ml, clear, colorless to faintly yellow (may be further diluted 20 fold in H2O)
chloroform: soluble
methanol: soluble

运输

dry ice

储存温度

−20°C

InChI

1S/C34H42N4O6/c39-29(30-22-44-30)18-9-3-8-16-25-31(40)36-26(20-23-12-4-1-5-13-23)32(41)37-27(21-24-14-6-2-7-15-24)34(43)38-19-11-10-17-28(38)33(42)35-25/h1-2,4-7,12-15,25-28,30H,3,8-11,16-22H2,(H,35,42)(H,36,40)(H,37,41)/t25-,26-,27-,28+,30-/m0/s1

InChI key

GXVXXETYXSPSOA-UFEOFEBPSA-N

应用

Trapoxin A has been used:
  • to study its effects on the inhibition of histone deacetylase 11 (HDAC11)
  • to study its effects on the inhibition of HDAC3 in human cell lines
  • to study its effects on the inhibition of HDAC6 in rat pyramidal neurons

生化/生理作用

Trapoxin A is a cyclotetrapeptide and a histone deacetylase (HDAC) inhibitor. It increases the level of chromatin acetylation associated with histone H3 at low nanomolar concentrations. Unlike the reversible HDAC inhibition induced by TCA, Trapoxin A irreversibly inhibites HDAC activity in crude cell lysates, and induces the accumulation of hyperacetylated core histones in a number of mammalian cell lines and tissues. Histone acetylation and methylation have been studied extensively for their anti-tumor activities in carcinogenesis and Trapoxin has been suggested as a potential anticancer agent for pre-clinical trials.

特点和优势

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.

制备说明

Trapoxin A is soluble in DMSO at a concentration ranging from 0.9-1.10 mg/ml and yields a clear, colorless to faint yellow solution. It is also soluble in chloroform and methanol.

相关产品

产品编号
说明
价格

象形图

Skull and crossbones
GHS06

警示用语：

Danger

危险声明

H301

预防措施声明

P301 + P310

危险分类

Acute Tox. 3 Oral

储存分类代码

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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M Yoshida et al.
Cancer chemotherapy and pharmacology, 48 Suppl 1, S20-S26 (2001-10-06)
Trichostatin A (TSA) and trapoxin (TPX), inhibitors of the eukaryotic cell cycle and inducers of morphological reversion of transformed cells, inhibit histone deacetylase (HDAC) at nanomolar concentrations. Recently, FK228 (also known as FR901228 and depsipeptide) and MS-275. antitumor agents structurally
S M Sternson et al.
Organic letters, 3(26), 4239-4242 (2002-01-11)
Seventy-two hundred potential inhibitors of the histone deacetylase (HDAC) enzyme family, based on a 1,3-dioxane diversity structure, were synthesized on polystyrene macrobeads. The compounds were arrayed for biological assays in a "one bead-one stock solution" format. Metal-chelating functional groups were
Betül Kitir et al.
Biochemistry, 56(38), 5134-5146 (2017-09-01)
Histone deacetylases (HDACs) are validated targets for treatment of certain cancer types and play numerous regulatory roles in biology, ranging from epigenetics to metabolism. Small molecules are highly important as tool compounds for probing these mechanisms as well as for
John Nielsen
Current opinion in chemical biology, 6(3), 297-305 (2002-05-23)
Combinatorial syntheses allow production of compound libraries in an expeditious and organized manner immediately applicable for high-throughput screening. Natural products possess a pedigree to justify quality and appreciation in drug discovery and development. Currently, we are seeing a rapid increase
[A new target of cancer therapy: advances in the study of histone deacetylase].
Ai-Lin Liu et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 40(7), 585-590 (2005-10-04)
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