C9492
毛壳素 来源于Chaetomium minutum
≥95% (HPLC)
别名:
(+)-Chaetocin A
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关于此项目
经验公式（希尔记法）:
C30H28N6O6S4
化学文摘社编号:
分子量:
696.84
MDL编号:
UNSPSC代码:
12352202
PubChem化学物质编号:
NACRES:
NA.77
质量水平
方案
≥95% (HPLC)
表单
powder
储存温度
2-8°C
SMILES字符串
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
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一般描述
毛壳素是一种具有抗菌和细胞抑制活性的真菌代谢物。它属于3,6-附睾硫代二酮哌嗪类，与胶质瘤毒素、孢子虫素、蜘蛛素、米扎氯、黄萎病素A和榅桲杀菌素属同一类。毛壳素是由两个五元环顺式融合而成的分子二聚体。
应用
来自毛壳菌属的毛壳素已用于测定对各种细胞的敏化作用。它还用于策动OS诱导异染色质形成的生物学功能。
生化/生理作用
毛壳素是S-腺苷甲硫氨酸的竞争性抑制剂。毛壳素对SU(VAR)3-9的特异性使该化合物成为研究异染色质介导基因抑制的极好工具。
毛壳素是一种抗菌霉菌毒素。作为赖氨酸特异性组蛋白甲基转移酶的特异性抑制剂，该化合物适合用于研究异染色质介导基因抑制。毛壳素是硫氧还蛋白还原酶-1 (TrxR1)的选择性竞争抑制剂，是其抗癌活性的公认机制。
甲基转移酶，帮助化合物用于异染色质介导的基因抑制研究。
制备说明
溶于DMSO。 在1mg / ml时，溶液在2-8℃下稳定1周。
警示用语：
Warning
危险声明
危险分类
Acute Tox. 4 Oral
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
dust mask type N95 (US), Eyeshields, Gloves
法规信息
涉药品监管产品
此项目有
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
Eriko Iwasa et al.
Journal of the American Chemical Society, 132(12), 4078-4079 (2010-03-10)
The first total synthesis of (+)-chaetocin has been accomplished in nine steps starting from known N-Cbz-N-Me-serine using radical alpha-bromination reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerization reaction of 12 as key reactions. The enantiomers show comparable inhibitory activity toward
Crescent R Isham et al.
Blood, 109(6), 2579-2588 (2006-11-09)
Chaetocin, a thiodioxopiperazine natural product previously unreported to have anticancer effects, was found to have potent antimyeloma activity in IL-6-dependent and -independent myeloma cell lines in freshly collected sorted and unsorted patient CD138(+) myeloma cells and in vivo. Chaetocin largely
Xiao-Gang Weng et al.
Theriogenology, 146, 162-170 (2019-12-04)
Aberrant epigenetic reprogramming is a major cause of the developmental failure of embryos after somatic cell nuclear transfer (SCNT). Histone H3 lysine 9 trimethylation (H3K9me3), a histone marker of transcriptional repression, is considered a key barrier to the development of
The molecular structure and absolute configuration of chaetocin
Weber H P
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, 28(10), 2945-2951 (1972)
Dorothea Greiner et al.
Nature chemical biology, 1(3), 143-145 (2006-01-13)
Histone methylation plays a key role in establishing and maintaining stable gene expression patterns during cellular differentiation and embryonic development. Here, we report the characterization of the fungal metabolite chaetocin as the first inhibitor of a lysine-specific histone methyltransferase. Chaetocin
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