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Purity: ≥98%
Chaetocin, a naturally occurring fungal mycotoxin extracted from Chaetomium, is a novel and non-specific inhibitor of the histone lysine methyltransferase (HMT) G9a with an IC50 of 2.5 μM. It belongs to the class of 3,6-epidithio-diketopiperazines. Chaetocin also inhibits thioredoxin reductase (TrxR) with an IC50 of 4 μM. Chaetocin was originally reported as the first lysine-specific histone methyltransferase inhibitor. Chaetocin can selectively reduce intracellular H3K9me2 and H3K9me3 levels but has no effect on other epigenetic modifications tested. In addition, Chaetocin can induce apoptosis in human melanoma cells, generating reactive oxygen species and the intrinsic mitochondrial pathway.
| ln Vitro |
Chaetin is a member of the 3-6-ethodithiodionepiperazine (ETP) class of compounds, and it was first isolated from the fermentation broth of Chaetomium. SU (VAR) 3-9 has an IC50 of 0.6 μM, making it a viable yeast substitute for S-adenosylmethionine. Chaetocin dSU (VAR) 3-9's human homologue has an IC50 of 0.8 μM. Other known Lys9 triangular HMTs with IC50 values of 2.5 and 3 mM, respectively, inhibit TrxR1-initiated turnover of the synthetic substrate DTNB in dose-responsive manner in cell-free tests [1]. These HMTs are geometric G9a and Neurospora crassa DIM5 chaetocin.
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| ln Vivo |
The Drosophila tissue cells can be cultured with or without SL-2. Cultivated cells are poisonous to chaetin. The initial cell density had a significant impact on the toxicity of chaetocin when it was introduced to the culture. There was a considerable decrease in the quantity of H3 molecules that were dimethylated at Lys9 (H3K9me2) after the cells were cultured for five days in the presence of 0.5 μM Chaetocin. Although not as dramatically as with higher concentrations, histones recovered from cells treated with 0.1 μM for shorter times also displayed a decrease in Lys9 methylation [1].
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| 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 |
| Molecular Formula |
C30H28N6O6S4
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| Molecular Weight |
696.8399
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| CAS # |
28097-03-2
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| SMILES |
O=C1N(C)[C@]2(CO)C(N3C1(SS2)C[C@@]4([H])[C@]3([H])NC5=C4C(N6C(N7[C@](C(N(C)[C@]8(CO)C7=O)=O)(SS8)C9)C9C%10=C6C=CC=C%10)=CC=C5)=O
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| InChi Key |
CNTRDQLQYLGSKO-KPCONVMXSA-N
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| InChi Code |
InChI=1S/C30H28N6O6S4/c1-32-23(39)27-11-16-20-17(31-21(16)35(27)25(41)29(32,12-37)45-43-27)7-5-9-19(20)34-18-8-4-3-6-14(18)15-10-28-24(40)33(2)30(13-38,46-44-28)26(42)36(28)22(15)34/h3-9,15-16,21-22,31,37-38H,10-13H2,1-2H3/t15?,16-,21-,22?,27?,28+,29+,30+/m1/s1
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| Synonyms |
Chaetocin; (3S,3'S,5aR,5aR,10bR,10'bR,11aS,11'aS)-2,2',3,3',5a,5'a,6,6'-octahydro-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-[10b,10'b(11H,11'H)-bi3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 26 mg/mL (~37.31 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.08 mg/mL (2.98 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (2.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4350 mL | 7.1752 mL | 14.3505 mL | |
| 5 mM | 0.2870 mL | 1.4350 mL | 2.8701 mL | |
| 10 mM | 0.1435 mL | 0.7175 mL | 1.4350 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
 Chaetocin inhibits thioredoxin reductase activity.Antioxid Redox Signal.2009 May;11(5):1097-106. |
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 Chaetocin less potently inhibits the activity of glutathione reductase or thioredoxin.Antioxid Redox Signal.2009 May;11(5):1097-106. |
 Chaetocin and other intact thiodioxopiperazines inhibit the ability of thioredoxin reductase to reduce its native substrate thioredoxin. |
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