Trichostatin A

Modify Date: 2024-01-03 09:34:19

Trichostatin A Structure
Trichostatin A structure
 Common Name Trichostatin A
CAS Number 58880-19-6 Molecular Weight 302.368
Density 1.1±0.1 g/cm3 Boiling Point N/A
Molecular Formula C17H22N2O3 Melting Point 141-143ºC
MSDS Chinese USA Flash Point N/A
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Trichostatin A


Trichostatin A is a potent and specific inhibitor of HDAC class I/II, with an IC50 value of 1.8 nM for HDAC.

 Names

Name trichostatin A
Synonym More Synonyms

 Trichostatin A Biological Activity

Description Trichostatin A is a potent and specific inhibitor of HDAC class I/II, with an IC50 value of 1.8 nM for HDAC.
Related Catalog
Target

HDAC:1.8 nM (IC50)
In Vitro Trichostatin A is a potent and specific inhibitor of HDAC class I/II, with an IC50 value of 1.8 nM for HDAC. Trichostatin A (TSA) inhibits proliferation of eight breast carcinoma cell lines with mean±SD IC50 of 124.4±120.4 nM (range, 26.4-308.1 nM). HDAC inhibitory activity of Trichostatin A is similar in all cell lines with mean IC50 of 2.4±0.5 nM (range, 1.5-2.9 nM)[1]. Trichostatin A (330 nM) increases Gαs protein expression in human myometrial cells, but does not increase Gαs mRNA levels[2]. Trichostatin A (20-75 nM) induces minimal cytotoxicity to adipose-derived stem cells (ADSCs), and enhances the osteogenic differentiation capacity of ADSCs[3]. In addition, Trichostatin A (0, 10, 100, 500 nM) dose-dependently decreases HDAC class I/II activity[4].
In Vivo Trichostatin A (500 μg/kg, s.c.) pronounces antitumor activity without causing any measurable toxicity in doses of up to 5 mg/kg by s.c. injection, in randomized controlled efficacy studies using the N-methyl-N-nitrosourea carcinogen-induced rat mammary carcinoma model[1].
Cell Assay Cells are cultured in a 96-well plate at 1×103 cells per well with 100 μL complete DMEM in the presence or absence of a HDAC inhibitor Trichostatin A for 72 h. Cytotoxicity is measured by performing WST-8 assay using a CCK-8 cell proliferation kit. The 450 nm absorbance is measured with a microplate reader. All experiments are carried out in triplicate and 3 independent experiments are performed[3].
Animal Admin Rats[1] Twelve rats are randomized to receive 500 μg/kg Trichostatin A in 50 μL DMSO, or 50 μL DMSO as vehicle control, by s.c. injection twice weekly for 4 weeks. In subsequent studies, 30 rats are randomized to receive Trichostatin A 500 μg/kg in 50 μL DMSO, or 50 μL DMSO as vehicle control, by s.c. injection daily for 4 weeks. Weekly tumor measurements, estimated tumor volumes, and body mass are recorded for each animal. Animals are sacrificed at the end of the 4-week study period; palpable tumors are resected and immediately snap-frozen in liquid nitrogen. Animals with tumors <2 cm in diameter or ulcerating tumors are withdrawn from study[1].
References

[1]. Vigushin DM et al. Trichostatin A is a histone deacetylase inhibitor with potent antitumor activity against breast cancer in vivo. Clin Cancer Res. 2001 Apr;7(4):971-6.

[2]. Karolczak-Bayatti M, et al. Expression of the GTP-Binding Protein Gαs in Human Myometrial Cells is Regulated by Ubiquitination and Protein Degradation: Involvement of Proteasomal Inhibition by Trichostatin A.,Reprod Sci. 2012 Aug 8.

[3]. Hu X, et al. Histone deacetylase inhibitor trichostatin A promotes the osteogenic differentiation of rat adipose-derived stem cells by altering the epigenetic modifications on Runx2 promoter in a BMP signaling-dependent manner.,Stem Cells Dev. 2012 Aug 8.

[4]. Azechi T, et al. Trichostatin A, an HDAC class I/II inhibitor, promotes Pi-induced vascular calcification via up-regulation of the expression of alkaline phosphatase. J Atheroscler Thromb. 2013;20(6):538-47.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Melting Point 141-143ºC
Molecular Formula C17H22N2O3
Molecular Weight 302.368
Exact Mass 302.163055
PSA 69.64000
LogP 2.77
Index of Refraction 1.578

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MI5215000
CHEMICAL NAME :
2,4-Heptadienamide, 7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7- oxo-
CAS REGISTRY NUMBER :
58880-19-6
LAST UPDATED :
198912
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C17-H22-N2-O3
MOLECULAR WEIGHT :
302.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Rodent - rat Embryo
DOSE/DURATION :
100 ug/L
REFERENCE :
ECREAL Experimental Cell Research. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.10- 1950- Volume(issue)/page/year: 177,122,1988

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302 + H312 + H332-H315-H317-H319-H335
Precautionary Statements P261-P280-P302 + P352 + P312-P304 + P340 + P312-P333 + P313
Personal Protective Equipment Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)
Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22
Safety Phrases 26-36
RIDADR NA 1993 / PGIII
WGK Germany 3
RTECS MI5215000
HS Code 2924299090

 Synthetic Route

 Customs

HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

Antibiotic A-300
2,4-Heptadienamide, 7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-, (2E,4E,6R)-
(2E,4E,6R)-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide
(R)-Trichostatin A
2,4-Heptadienamide, 7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-, (2E,4E,6R)- (9CI)
TSA
2,4-Heptadienamide, 7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-, (2E,4E,6R)-
2,4-Heptadienamide, 7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-
Trichostatin A
7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide
7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6R-dimethyl-7-oxo-2E,4E-heptadienamide
(2E,4E,6R)-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
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