58880-19-6

Basic information

• Product Name: TRICHOSTATIN A
• Synonyms: 7-[4-(DIMETHYLAMINO)PHENYL]-N-HYDROXY-4,6R-DIMETHYL-7-OXO-2E,4E-HEPTADIENAMIDE;4,6-DIMETHYL-7-[P-DIMETHYLAMINOPHENYL]-7-OXAHEPTA-2,4-DIENOHYDROXAMIC ACID;4,6-DIMETHYL-7-[P-DIMETHYLAMINOPHENYL]-7-OXOHEPTA-2,4-DIENOHYDROXAMIC ACID;7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-4-heptadienamide;TSA;TRICHOSTATIN A;TRICHOSTATIN A, STREPTOMYCES SPECIES;Trichostatin A, Streptomyces sp.
• CAS NO: 58880-19-6
• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.37
• EINECS: 611-758-2
• Product Categories: Anti Cancer Research;Inhibitor;antibiotic;API;Inhibitors
• Mol File: 58880-19-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 140-143℃
• Appearance: /
• Density: 1.139
• Refractive Index: 136 ° (C=0.3, MeOH)
• Storage Temp.: −20°C
• Solubility: ethanol: 1 mg/mL
• PKA: 8.93±0.23(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
• Merck: 14,9649
• CAS DataBase Reference: TRICHOSTATIN A(CAS DataBase Reference)
• NIST Chemistry Reference: TRICHOSTATIN A(58880-19-6)
• EPA Substance Registry System: TRICHOSTATIN A(58880-19-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-43
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: MI5215000
• Hazardous Substances Data: 58880-19-6(Hazardous Substances Data)

Usage

Description

TRICHOSTATIN A is a potent and selective histone deacetylase (HDAC) inhibitor, primarily composed of hydroxamic acid. It is known for its ability to induce reversion of ras transformed cells to normal morphology and dedifferentiation of primordial germ cells into embryonic germ cells. As a solid compound, it possesses cell permeability and is active in vivo.

Uses

Used in Anticancer Applications:
TRICHOSTATIN A is used as an anticancer agent in the pharmaceutical industry for its ability to inhibit fibrosis in vitro and in vivo. It acts as a potent differentiation inducer of friend leukemic cells and enhances the cytotoxic efficacy of anticancer drugs that target DNA. Additionally, it displays antifungal, antiprotozoan, and antitumor activity.
Used in Drug Delivery Systems:
In the field of drug delivery, TRICHOSTATIN A is utilized to overcome limitations associated with its use. Novel drug delivery systems have been developed to improve its delivery, bioavailability, and therapeutic outcomes against cancer cells. Various organic and metallic nanoparticles are employed as carriers for TRICHOSTATIN A delivery.
Used in Stem Cell Research:
TRICHOSTATIN A is used as a histone deacetylase inhibitor in stem cell testing to study its effect on transcriptome changes. This application is crucial in understanding the role of HDAC inhibition in stem cell biology and its potential implications in regenerative medicine.
Used in Primary Pituitary Cell Cultures:
In the field of endocrinology, TRICHOSTATIN A is used to inhibit histone deacetylase (HDAC) class I, II, or III in primary pituitary cell cultures. This application aids in investigating the insulin control of the endogenous human growth hormone gene (hGH), providing insights into the regulation of growth hormone production.
Used in HDAC Inhibition Experiments:
TRICHOSTATIN A is employed in cellular and molecular biology research to treat cells for HDAC inhibition experiments. This application is essential for understanding the role of HDAC inhibition in various cellular processes and its potential therapeutic applications.

Biological Activity

Selective and potent inhibitor of histone deacetylase (K i = 3.4 nM). Active in vivo . Potential anti-cancer agent. Induces accelerated dedifferentiation of primordial germ cells (PGCs) into embryonic germ (EG) cells.

Biochem/physiol Actions

Inhibits histone deacetylase at nanomolar concentrations; resultant histone hyperacetylation leads to chromatin relaxation and modulation of gene expression. May be involved in cell cycle progression of several cell types, inducing cell growth arrest at both G and G/M phases; may induce apoptosis. Enhances the efficacy of anticancer agents that target DNA.

References

1) Yoshida et al. (1990), Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A ; J. Biol. Chem., 265 17174 2) Futamura et al. (1995), Trichostatin A inhibits both ras-induced neurite outgrowth of PC12 cells and morphological transformation of NIH3T3 cells; Oncogene, 10 1119 3) Durcova-Hills et al. (2008), Reprogramming Primordial Germ Cells into Pluripotent Stem Cells; PLoS-One, 3 e3531

InChI:InChI=1/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+

Upstream product

• 122222-87-1 O-(2-methoxypropyl)-(S)-trichostatin A 
• 122222-87-1 O-(2-methoxypropyl)-(R)-trichostatin A 
• 934246-98-7 ethyl (2E,4E)-(6R,7R)-7-[4-(dimethylamino)phenyl]-7-hydroxy-4,6-dimethylhepta-2,4-dienoate 
• 122222-78-0 (S)-3-(4-Dimethylamino-phenyl)-3-(1-methoxy-1-methyl-ethoxy)-2-methyl-propionaldehyde 
• 122222-78-0 (R)-3-(4-Dimethylamino-phenyl)-3-(1-methoxy-1-methyl-ethoxy)-2-methyl-propionaldehyde 
• 122222-72-4 3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-2-(S)-methyl-1-propanol 
• 122222-72-4 3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-2-(R)-methyl-1-propanol 
• 122222-76-8 3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol 
• 122222-76-8 3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(S)-methyl-1-propanol 
• 122222-81-5 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol 
• 122222-81-5 2,4-(S)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol 
• 114127-18-3 (+)-(R)-trichostatin acid 
• 114127-17-2 (S)-trichostatic acid 
• 122222-83-7 (E)-(R)-5-(4-Dimethylamino-phenyl)-5-(1-methoxy-1-methyl-ethoxy)-2,4-dimethyl-pent-2-enal 

Downstream Products

• 1298085-51-4 2,3-dihydrotrichostatin A 
• 68676-88-0 trichostatin C 

Relevant articles and documents

Evolution of concise and flexible synthetic strategies for trichostatic acid and the potent histone deacetylase inhibitor trichostatin A

(R)-(+)-Trichostatic acid and (R)-(+)-trichostatin A (TSA) are natural products that have attracted considerable attention in the field of epigenetic therapies. TSA in particular is a naturally occurring hydroxamic acid having potent activity as a histone deacetylase inhibitor (HDACi) and having significant potential for treatment of a myriad of genetically based diseases. Development of TSA and other trichostatic acid derivatives into useful small-molecule therapies has been hindered by the low natural abundance and high cost associated with these compounds. We report herein our collective efforts towards the development of concise and scalable routes for the synthesis of trichostatic acid and TSA in both racemic and enantioenriched forms. Three independent synthetic pathways were developed with varying degrees of efficiency and convergency. In the first synthesis, the key step was a vinylogous Horner-Wadsworth-Emmons condensation. A Marshall propargylation reaction was used as the key step in the second synthesis, and Pd-catalyzed α-alkenylation of a ketone zinc enolate by using various functionalized alkenyl or dienyl halides was developed for the third synthesis. The second pathway proved to be readily amenable to an enantioselective modification, and both the second and third pathways were straightforwardly adapted for the facile preparation of new analogues of trichostatic acid and TSA. Three synthetic strategies have been developed for trichostatic acid and trichostatin A. Each strategy has a different key bond-forming step; a vinylogous Horner-Wadsworth-Emmons condensation, a Marshall propargylation, and coupling of a ketone enolate with various alkenyl halides. Two of the syntheses were efficient and able to produce analogues. Two of the syntheses were enantioselective. Copyright

OCULAR HYPOTENSIVE AGENT COMPRISING COMPOUND CAPABLE OF INHIBITING HISTONE DEACETYLASE AS ACTIVE INGREDIENT

An object of the present invention is to find a novel pharmacological effect of a compound having an HDAC inhibitory effect. The compound having an HDAC inhibitory effect of the invention has an excellent effect of cell morphological change on trabecular meshwork cells and/or effect of intraocular pressure reduction, and is therefore useful as a preventive and/or therapeutic agent for a disease considered to be associated with aqueous humor circulation and/or intraocular pressure, particularly as a preventive and/or therapeutic agent for glaucoma or ocular hypertension.

Efficient, enantioselective organocatalytic synthesis of trichostatin A

An efficient, highly stereocontrolled total synthesis of trichostatin A (1) has been achieved in 9 steps with 17.4% overall yield and >99% optical purity from readily available achiral starting materials. The key features of this synthesis include the L-proline-promoted, highly enantioselective cross-aldol reaction as a crucial step for the construction of the C-6 chiral center and the minimization of racemization by final step oxidation of the OH group to a ketone at position 7.