133155-89-2

Basic information

• Product Name: trapoxin A
• Synonyms: trapoxin A;(4aR,7S,10S,13S)-10,13-Dibenzyl-7-[6-oxo-6-[(S)-oxiranyl]hexyl]-1,2,3,4,9,10-hexahydro-4aH-6,9,12,14a-tetraazabenzocyclododecene-5,8,11,14(6H,7H,12H,13H)-tetrone;Cyclo[L-Phe-L-Phe-D-Hpr-6-[2-[(S)-oxiranyl]-2-oxoethyl]-L-Nle-];RF-1023A;Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl);Cyclo[(aS,2S)-a-amino-h-oxo-2-oxiraneoctanoyl-L-phenylalanyl-L-phenylalanyl-(2R)-2-piperidinecarbonyl]
• CAS NO: 133155-89-2
• Molecular Formula: C₃₄H₄₂N₄O₆
• Molecular Weight: 602.72
• Mol File: 133155-89-2.mol

Chemical Properties

• Boiling Point: 928.3°Cat760mmHg
• Flash Point: 515.2°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble0.9-1.10 mg/ml, clear, colorless to faintly yellow
• CAS DataBase Reference: trapoxin A(CAS DataBase Reference)
• NIST Chemistry Reference: trapoxin A(133155-89-2)
• EPA Substance Registry System: trapoxin A(133155-89-2)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 133155-89-2(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
Trapoxin A is used as a research tool for studying its effects on the inhibition of histone deacetylase 11 (HDAC11), HDAC3 in human cell lines, and HDAC6 in rat pyramidal neurons. This helps in understanding the role of HDACs in various cellular processes and their potential as therapeutic targets.
Used in Cancer Research:
Trapoxin A is used as an inhibitor of oncogene v-sis transformed NIH3T3 cells (sis/NIH3T3), with an IC50 of approximately 200 ng/ml. It demonstrates detransformation activity, flattening sis/NIH3T3 cells when used at a concentration of 1 ng/ml.
Used in Cell Cycle Research:
Trapoxin A is used to study its effects on the cell cycle, as it halts the cell cycle at the G2 phase in 3Y1 fibroblasts when used at a concentration of 10 nM.
Used in Drug Resistance Research:
Trapoxin A is used to study its effects on the growth inhibition of TR303 cells, which are resistant to trichostatin A, at a concentration of 50 ng/ml. This helps in understanding the mechanisms of drug resistance and potential strategies to overcome it.

Biochem/physiol Actions

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.

InChI:InChI=1/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

Relevant articles and documents

Total Synthesis of Trapoxin A, a Fungal HDAC Inhibitor from Helicoma ambiens

Peptide modification reactions, e.g., via palladium-catalyzed allylic alkylations, are useful tools for the synthesis of peptides containing interesting nonproteinogenic amino acids, which are often essential for the biological activity of natural products and drugs. Herein we report the utilization of such modification reactions in the first total synthesis of trapoxin A, a naturally occurring tetrapeptidic histone deacetylase (HDAC) inhibitor.