| Chemical & Physical Properties | |
|---|---|
| CAS Number | 28097-03-2 |
| Catalog No. | 2A-1177706 |
| Chinese Name | 毛壳素 |
| Synonyms | (+)-chaetocin A; 'bR,11aS,11'aS); Chetocin |
| Molecular Formula | C30H28N6O6S4 |
| Molecular Weight | 696.84 |
| Purity | ≥95 (HPLC) |
| Density | 1.9±0.1 g/cm3 |
| Appearance | powder |
| Storage Condition | 2~8°C |
| Packaging | III |
| Application | Chaetocin is a specific inhibitor of histone methyltransferase (HMT) SU(VAR)3-9 with an IC50 value of 0.6 μM. Chaetocin also inhibits thioredoxin reductase (TrxR) with an IC50 value of 4 μM. |
| PubChem ID | 24893002 |
| MDL Number | MFCD00133163 |
| SMILES | CN1C(=O)C23CC4(C(Nc5ccccc45)N2C(=O)C1(CO)SS3)C67CC89SSC(CO)(N(C)C8=O)C(=O)N9C6Nc%10ccccc7%10 |
| InChI | 1S/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3 |
| InChI Key | PZPPOCZWRGNKIR-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352202 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/178292_2_28097_03_2.pdf |
| Bioactivity | 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. Chemical & Physical Properties 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 InChIKey PZPPOCZWRGNKIR-PNVYSBBASA-N SMILES CN1C(=O)C23CC4(C56CC78SSC(CO)(C(=O)N7C5Nc5ccccc56)N(C)C8=O)c5ccccc5NC4N2C(=O)C1(CO)SS3 Storage condition 2~8°C |
| Use of | 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. Properties Articles21 Name Chaetocin Synonym More Synonyms Chaetocin Biological Activity 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 IC50: 0.6 μM (HMT)[1], 4 μM (TrxR)[2] 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. Chemical & Physical Properties Molecular Formula C30H28N6O6S4 Exact Mass 696.095337 PSA 246.96000 Index of Refraction 1.930 InChIKey PZPPOCZWRGNKIR-PNVYSBBASA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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