Chaetocin

Modify Date: 2024-01-09 13:37:04

Chaetocin structure	Common Name	Chaetocin
	CAS Number	28097-03-2	Molecular Weight	696.840
	Density	1.9±0.1 g/cm3	Boiling Point	N/A
	Molecular Formula	C₃₀H₂₈N₆O₆S₄	Melting Point	N/A
	MSDS	Chinese USA	Flash Point	N/A
	Symbol	GHS07	Signal Word	Warning

Use of Chaetocin

Chaetocin is a specific inhibitor of the histone methyltransferase (HMT) SU(VAR)3-9 with an IC50 of 0.6 μM for SU(VAR)3-9. It also inhibits thioredoxin reductase (TrxR) with an IC50 of 4 μM.

Name	Chaetocin
Synonym	More Synonyms

Description	Chaetocin is a specific inhibitor of the histone methyltransferase (HMT) SU(VAR)3-9 with an IC50 of 0.6 μM for SU(VAR)3-9. It also inhibits thioredoxin reductase (TrxR) with an IC50 of 4 μM.
Related Catalog	Signaling Pathways >> Epigenetics >> Histone Methyltransferase Natural Products >> Saccharides and Glycosides Research Areas >> Cancer
Target	IC50: 0.6 μM (HMT)[1], 4 μM (TrxR)[2]
In Vitro	Chaetocin is initially isolated from the fermentation broth of chaetomium minutum and belongs to the class of 3-6 epidithio-diketopiperazines (ETPs). The IC50 for SU(VAR)3-9 is 0.6 μM and acts as a competitive inhibitor for S-adenosylmethionine. Chaetocin inhibits the human ortholog of dSU(VAR)3-9 with a similar IC50 value of 0.8 μM. It inhibits other known Lys9-specific HMTs such as mouse G9a and Neurospora crassa DIM5 with a higher IC50 values of 2.5 and 3 mM, respectively[1]. Chaetocin inhibits TrxR1-initiated turnover of the synthetic substrate DTNB in a cell-free assay in a dose-responsive manner with an IC50 of about 4 μM[2].
In Vivo	SL-2 Drosophila tissue cells are cultured in the presence or absence of the inhibitor. Chaetocin has a toxic effect on cells grown in culture. Toxicity is highly dependent on the initial cell density when chaetocin is added to the culture. The number of H3 molecules dimethylated at Lys9 (H3K9me2) is markedly reduced when cells are grown in medium containing 0.5 μM chaetocin after 5 d. Histones isolated from cells treated with 0.1 μM and for a shorter time also shows a drop in Lys9 methylation, but not as strongly as with the higher concentration[1].
Cell Assay	HeLa cells are transfected with 1 μg pcDNA or pcDNA-Trx. Twenty four h after transfection the cells are treated with either DMSO, 100 nM chaetocin or 100 nM doxorubicin for 24 h. The cells are then trypsinized and manually counted in trypan blue to exclude dead cells. For immunoblotting (24 h after transfections), cells are trypsinized, ished in cold PBS, and lysed in CelLytic lysis buffer containing protease inhibitors. Protein is analyzed by BCA assay and lysates are electrophoresed on 15% SDS-PAGE gels and transferred to nitrocellulose. Immunoblotting for thioredoxin and actin is then performed[2].
References	[1]. Greiner D, et al. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat Chem Biol. 2005 Aug;1(3):143-5. [2]. Tibodeau JD, et al. The anticancer agent chaetocin is a competitive substrate and inhibitor of thioredoxin reductase. Antioxid Redox Signal. 2009 May;11(5):1097-106.

Density	1.9±0.1 g/cm3
Molecular Formula	C₃₀H₂₈N₆O₆S₄
Molecular Weight	696.840
Exact Mass	696.095337
PSA	246.96000
LogP	3.10
Index of Refraction	1.930
Storage condition	2~8°C

Chaetocin MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FM3032000

CHEMICAL NAME :: Chetocin

CAS REGISTRY NUMBER :: 28097-03-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C30-H28-N6-O6-S4

MOLECULAR WEIGHT :: 696.88

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 4(1),170,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1700 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 4(1),170,1980

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302 + H312 + H332
Precautionary Statements	P280
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn
Risk Phrases	20/21/22
RIDADR	UN 1544
RTECS	FM3032000
Packaging Group	III
Hazard Class	6.1(b)

(+)-chaetocin A...

CAS#:28097-04-3

~89%

Chaetocin

CAS#:28097-03-2

Literature: Kim, Justin; Movassaghi, Mohammad Journal of the American Chemical Society, 2010 , vol. 132, # 41 p. 14376 - 14378

CAS#:1219135-51-9

~43%

Chaetocin

CAS#:28097-03-2

Literature: Iwasa, Eriko; Hamashima, Yoshitaka; Fujishiro, Shinya; Eisuke, Higuchi; Ito, Akihiro; Yoshida, Minoru; Sodeoka, Mikiko Journal of the American Chemical Society, 2010 , vol. 132, # 12 p. 4078 - 4079

CAS#:1219135-73-5

~6%

Chaetocin

CAS#:28097-03-2

Precursor 2
CAS#:28097-04-3 (+)-chaetocin A... CAS#:1219135-51-9
DownStream 0

Inhibition of histone H3K9 methyltransferases by gliotoxin and related epipolythiodioxopiperazines.

J. Antibiot. 65(5) , 263-5, (2012)

Individual epigenetic status of the pathogenic D4Z4 macrosatellite correlates with disease in facioscapulohumeral muscular dystrophy.

Clin. Epigenetics. 7(1) , 37, (2015)

Both forms of facioscapulohumeral muscular dystrophy (FSHD) are associated with aberrant epigenetic regulation of the chromosome 4q35 D4Z4 macrosatellite. Chromatin changes due to large deletions of h...

Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: reducing cytotoxicity by structural simplification.

Bioorg. Med. Chem. Lett. 23(3) , 733-6, (2013)

Chaetocin (1), a structurally complex epidithiodiketopiperazine (ETP) alkaloid produced by Chaetomium minutum, is a potent inhibitor of protein lysine methyltransferase G9a, which plays important role...

(3S,3'S)-3,3'-bis-hydroxymethyl-2,2'-dimethyl-(5at,10bt,5'at',10'bt')-2,3,5a,6,2',3',5'a,6'-octahydro-[10b,10'b]bi[3r,11ac-epidisulfano-pyrazino[1',2':1,5]pyrrolo[2,3-b]indolyl]-1,4,1',4'-tetraone

(+)-chaetocin A

(1S,1'S,3R,3'R,11R,11'R,14S,14'S)-14,14'-Bis(hydroxymethyl)-18,18'-dimethyl-3,3'-bi(15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0.0.0]octadecane)-4,4',6,6',8,8'-hexaene-13,13',17,17 ;'-tetrone

'bR,11aS,11'aS)

Chetocin

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Chaetocin

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