Chetomin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00633 |
| CAS | 1403-36-7 |
| Molecular Weight | 710.87 |
| Molecular Formula | C31H30N6O6S4 |
| Purity | ≥98% by HPLC |
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Description
It is produced by the strain of Chaetomium cochloides , Ch.globosum, Ch.fuunienlum, Ch.elatun, Ch.spirale and Verticillium cinnabarium. Chetomin is a natural metabolite produced by several species of the genus chaetomium. It is an epidithiodioxopiperazine and is an inhibitor of hypoxia-inducible factor (HIF). It inhibits interaction of HIF1α and HIF2α with transcriptional co-activators p300 and cAMP response element binding (CREB) protein (CBP). It decreases tumor growth by attenuating hypoxia-inducible transcription and disrupting the ability of tumors to adapt to hypoxia. It also suppresses the proliferation of LPS-induced mouse spleen lymphocytes. It may be used as an antibacterial agent and is used in antitumor research. It also may be useful in radiotherapeutic.
Specification
| Synonyms | CTM; NSC-289491; NSC 289491; NSC289491; Chaetomin; (3S,5aR,10bS,11aS)-2,3,5a,6,10b,11-Hexahydro-3-(hydroxymethyl)-10b-[(1S,4S)-3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]oct-1-yl]methyl]-1H-indol-1-yl]-2-methyl-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione |
| Storage | -20° C |
| IUPAC Name | 14-(hydroxymethyl)-3-[3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]octan-1-yl]methyl]indol-1-yl]-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione |
| Canonical SMILES | CN1C(=O)C2(N(C(=O)C1(SS2)CC3=CN(C4=CC=CC=C43)C56CC78C(=O)N(C(C(=O)N7C5NC9=CC=CC=C69)(SS8)CO)C)C)CO |
| InChI | InChI=1S/C31H30N6O6S4/c1-33-25(42)30(15-38)34(2)23(40)28(33,44-46-30)12-17-13-36(21-11-7-4-8-18(17)21)27-14-29-24(41)35(3)31(16-39,47-45-29)26(43)37(29)22(27)32-20-10-6-5-9-19(20)27/h4-11,13,22,32,38-39H,12,14-16H2,1-3H3 |
| InChI Key | ZRZWBWPDBOVIGQ-UHFFFAOYSA-N |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | gram-positive bacteria; gram-negative bacteria; fungi; mycobacteria |
| Solubility | Soluble in DMSO, acetone and ethyl acetate. |
Reference Reading
1.Chetomin induces apoptosis in human triple-negative breast cancer cells by promoting calcium overload and mitochondrial dysfunction.
Dewangan J;Srivastava S;Mishra S;Pandey PK;Divakar A;Rath SK Biochem Biophys Res Commun. 2018 Jan 8;495(2):1915-1921. doi: 10.1016/j.bbrc.2017.11.199. Epub 2017 Dec 5.
Human triple-negative breast cancer (TNBC) is poorly diagnosed and unresponsive to conventional hormone therapy. Chetomin (CHET), a fungal metabolite synthesized by Chaetomium cochliodes, has been reported as a promising anticancer and antiangiogenic agent but the complete molecular mechanism of its anticancer potential remains to be elucidated. In our study, we explored the anti-neoplastic action of CHET on TNBC cells. Cytotoxicity studies were performed in human TNBC cells viz. MDA-MB-231 and MDA-MB-468 cells by Sulforhodamine B assay. It exhibited antiproliferative response and induced apoptosis in both the cell types. Cell cycle analysis revealed that it increases the sub G0/G1 phase cell population. Modulation of mitochondrial membrane potential, activation of caspase 3/7 and a remarkable increase in the expression of cleaved PARP and increased chromatin condensation was observed after CHET treatment in MDA-MB-231 and MDA-MB-468 cells. Additionally, an elevated level of intracellular Ca;2+; played an important role in CHET mediated cell death response. Calcium overload in mitochondria led to release of cytochrome c which in turn triggered caspase-3 mediated cell death. Inhibition of calcium signalling using BAPTA-AM reduced apoptosis confirming the involvement of calcium signalling in CHET induced cell death.
2.Epidithiodiketopiperazines (ETPs) exhibit in vitro antiangiogenic and in vivo antitumor activity by disrupting the HIF-1α/p300 complex in a preclinical model of prostate cancer.
Reece KM;Richardson ED;Cook KM;Campbell TJ;Pisle ST;Holly AJ;Venzon DJ;Liewehr DJ;Chau CH;Price DK;Figg WD Mol Cancer. 2014 Apr 28;13:91. doi: 10.1186/1476-4598-13-91.
The downstream targets of hypoxia inducible factor-1 alpha (HIF-1α) play an important role in tumor progression and angiogenesis. Therefore, inhibition of HIF-mediated transcription has potential in the treatment of cancer. One attractive strategy for inhibiting HIF activity is the disruption of the HIF-1α/p300 complex, as p300 is a crucial coactivator of hypoxia-inducible transcription. Several members of the epidithiodiketopiperazine (ETP) family of natural products have been shown to disrupt the HIF-1α/p300 complex in vitro; namely, gliotoxin, chaetocin, and chetomin. Here, we further characterized the molecular mechanisms underlying the antiangiogenic and antitumor effects of these ETPs using a preclinical model of prostate cancer. In the rat aortic ring angiogenesis assay, gliotoxin, chaetocin, and chetomin significantly inhibited microvessel outgrowth at a GI50 of 151, 8, and 20 nM, respectively. In vitro co-immunoprecipitation studies in prostate cancer cell extracts demonstrated that these compounds disrupted the HIF-1α/p300 complex. The downstream effects of inhibiting the HIF-1α/p300 interaction were evaluated by determining HIF-1α target gene expression at the mRNA and protein levels.
3.Mycotoxin production by Chaetomium spp. and related fungi.
Sekita S;Yoshihira K;Natori S;Udagawa S;Muroi T;Sugiyama Y;Kurata H;Umeda M Can J Microbiol. 1981 Aug;27(8):766-72.
Screening for mycotoxin production by Chaetomium spp. and related fungi on rice culture was conducted by a combination of cytotoxicity tests using HeLa cells and thin-layer chromatography. Producers of sterigmatocystin, O-methylsterigmatocystin, chaetochromin, chaetocin, chetomin, cochliodinols, and mollicellin G were found and the taxonomic significance of these findings is discussed.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
