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 (58880-19-6) is a potent and selective histone deacetylase (HDAC) inhibitor (Ki = 3.4 nM). Induces reversion of ras transformed cells to normal morphology. Trichostatin A induces dedifferentiation of primordial germ cells into embryonic germ cells. Cell permeable and active in vivo.

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 58880-19-6 differently. You can refer to the following data:
1. Trichostatin A is a known inhibitor of fibrosis in vitro and in vivo, and is used as an anticancer agent. Potent differentiation inducer of friend leukemic cells.
2. Trichostatin A is a histone deacetylase inhibitor that enhances the cytotoxic efficacy of anticancer drugs that target DNA. Trichostatin A displays antifungal, antiprotozoan and antitumour activity
3. Trichostatin A, ready-made solution has been used:as a histone deacetylase inhibitor to study its effect on transcriptome changes by stem cell testingto inhibit histone deacetylase (HDAC) class I, II, or III in primary pituitary cell cultures and to investigate insulin control of endogenous human growth hormone gene (hGH)to treat cells for the HDAC inhibition experiments

General Description

Trichostatin A is a compound of primary hydroxamic acid.

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

• 1334686-47-3 C₂₃H₃₆N₂O₃Si 
• 114127-18-3 (+)-(R)-trichostatin acid 
• 921213-02-7 (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethyl-2,4-heptadienoic acid 
• 1334686-43-9 4-[(2R)-1-methoxy-2-methylpent-3-yn-1-yl]-N,N-dimethylaniline 
• 1334686-42-8 4-[(2R)-1-methoxy-2-methylbut-3-yn-1-yl]-N,N-dimethylaniline 
• 1334686-41-7 (R)-1-[4-(dimethylamino)phenyl]-2-methylbut-3-yn-1-ol 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 122222-84-8 methyl 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate 
• 122222-84-8 methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate 
• 122222-74-6 3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(R)-methylpropane 
• 122222-74-6 3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(S)-methylpropane 
• 122222-79-1 ethyl 2,4-(S)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate 
• 122222-79-1 ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate 
• 122222-85-9 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid 

Downstream Products

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

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.