WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H130493
CAS#: 133155-89-2
Description: Trapoxin A is a cyclotetrapeptide histone deacetylase (HDAC) inhibitor, irreversibly inhibiting HDAC activity in crude cell lysates and inducing hyperacetylation in histones.
Hodoodo Cat#: H130493
Name: Trapoxin A
CAS#: 133155-89-2
Chemical Formula: C34H42N4O6
Exact Mass: 602.31
Molecular Weight: 602.732
Elemental Analysis: C, 67.75; H, 7.02; N, 9.30; O, 15.93
Synonym: Trapoxin-A, RF 1023A, RF-1023A, RF1023A, RF-1023-A, RF1023-A, RF1023 A
IUPAC/Chemical Name: Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl); RF 1023A
InChi Key: GXVXXETYXSPSOA-UFEOFEBPSA-N
InChi Code: 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
SMILES Code: O=C([C@@]1(N(CCCC1)C([C@@H](NC2=O)CC3=CC=CC=C3)=O)[H])N[C@H](C(N[C@H]2CC4=CC=CC=C4)=O)CCCCCC([C@@H]5CO5)=O
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, chloroform, and methanol
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 602.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1. Watson PR, Gupta S, Hosseinzadeh P, Brown BP, Baker D, Christianson DW. Macrocyclic Octapeptide Binding and Inferences on Protein Substrate Binding to Histone Deacetylase 6. ACS Chem Biol. 2023 Apr 21;18(4):959-968. doi: 10.1021/acschembio.3c00113. Epub 2023 Apr 7. PMID: 37027789; PMCID: PMC10130746.
2. Zalloum WA, Zalloum N. Comparative QM/MM Molecular Dynamics and Umbrella Sampling Simulations: Interaction of the Zinc-Bound Intermediate Gem-Diolate Trapoxin A Inhibitor and Acetyl-l-lysine Substrate with Histone Deacetylase 8. J Phys Chem B. 2021 May 27;125(20):5321-5337. doi: 10.1021/acs.jpcb.1c01696. Epub 2021 May 17. PMID: 33998791.
3. Itazaki H, Nagashima K, Sugita K, Yoshida H, Kawamura Y, Yasuda Y, Matsumoto K, Ishii K, Uotani N, Nakai H, et al. Isolation and structural elucidation of new cyclotetrapeptides, trapoxins A and B, having detransformation activities as antitumor agents. J Antibiot (Tokyo). 1990 Dec;43(12):1524-32. doi: 10.7164/antibiotics.43.1524. PMID: 2276972.
4. Nakai H, Nagashima K, Itazaki H. Structure of a new cyclotetrapeptide trapoxin A. Acta Crystallogr C. 1991 Jul 15;47 ( Pt 7):1496-9. doi: 10.1107/s0108270190012987. PMID: 1930826.
5. Aoki F, Worrad DM, Schultz RM. Regulation of transcriptional activity during the first and second cell cycles in the preimplantation mouse embryo. Dev Biol. 1997 Jan 15;181(2):296-307. doi: 10.1006/dbio.1996.8466. PMID: 9013938.
6. Chireux M, Espinos E, Bloch S, Yoshida M, Weber MJ. Histone hyperacetylating agents stimulate promoter activity of human choline acetyltransferase gene in transfection experiment. Brain Res Mol Brain Res. 1996 Jul;39(1-2):68-78. doi: 10.1016/0169-328x(96)00006-x. PMID: 8804715.
7. Van Lint C, Emiliani S, Verdin E. The expression of a small fraction of cellular genes is changed in response to histone hyperacetylation. Gene Expr. 1996;5(4-5):245-53. PMID: 8723390; PMCID: PMC6138027.
8. Yoshida M, Horinouchi S, Beppu T. Trichostatin A and trapoxin: novel chemical probes for the role of histone acetylation in chromatin structure and function. Bioessays. 1995 May;17(5):423-30. doi: 10.1002/bies.950170510. PMID: 7786288.
9. Kijima M, Yoshida M, Sugita K, Horinouchi S, Beppu T. Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase. J Biol Chem. 1993 Oct 25;268(30):22429-35. PMID: 8226751.
10. Ho TT, Peng C, Seto E, Lin H. Trapoxin A Analogue as a Selective Nanomolar Inhibitor of HDAC11. ACS Chem Biol. 2023 Apr 21;18(4):803-809. doi: 10.1021/acschembio.2c00840. Epub 2023 Mar 28. PMID: 36977486; PMCID: PMC10127203.
