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26166-39-2

中文名稱 殼二孢氯素
英文名稱 ascochlorin
CAS 26166-39-2
分子式 C23H29ClO4
分子量 404.93
MOL 文件 26166-39-2.mol
26166-39-2 結(jié)構(gòu)式 26166-39-2 結(jié)構(gòu)式

基本信息

中文別名
殼二孢氯素
英文別名
Nsc 287492
ascochlorin
Ilicicolin D
Ll-Z 1272 gamma
Antibiotics LL-Z 1272g
Antibiotic ll-Z1272 gamma
LL-Z 1272 gaMMa, Ilicicolin D
beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (E,E)-
5-Chloro-2,4-dihydroxy-6-methyl-3-[(2E,4Z)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde
3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R)-1β,2β,6β-trimethyl-3-oxocyclohexyl]-2,4-pentadienyl]benzaldehyde

物理化學(xué)性質(zhì)

熔點(diǎn)172-174 °C
沸點(diǎn)556.9±39.0 °C(Predicted)
密度1.199±0.06 g/cm3(Predicted)
儲存條件-20°C
溶解度可溶于DMSO
酸度系數(shù)(pKa)6.26±0.50(Predicted)
形態(tài)粉末狀

安全數(shù)據(jù)

WGK Germany3
毒性mouse,LD50,intraperitoneal,20mg/kg (20mg/kg),Journal of Antibiotics. Vol. 21, Pg. 539, 1968.

常見問題列表

生物活性
Ascochlorin (Ilicicolin D),異戊二烯類抗生素。Ascochlorin 主要通過抑制 STAT3 信號級聯(lián)介導(dǎo)其抗腫瘤作用。Ascochlorin 誘導(dǎo)細(xì)胞凋亡 (apoptosis)。具有抗炎活性。
靶點(diǎn)

STAT3

Apoptosis

體外研究

Ascochlorin (Ilicicolin D) (10-50 μM; 24-72 hours) inhibits the viability of HepG2, HCCLM3 and Huh7 cells in a time and dose dependent manner.
Ascochlorin (50 μM; 48 hours) induces apoptosis in HCC cells.
Ascochlorin (1-50 μM) significantly suppresses the production of nitric oxide (NO) and prostaglandin E2 (PGE2) and decreases the gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in a dose-dependent manner. Ascochlorin inhibits the mRNA expression and the protein secretion of interleukin (IL)-1β and IL-6 but not tumor necrosis factor (TNF)-α in LPS-stimulated RAW 264.7 macrophage cells. Ascochlorin suppresses nuclear translocation and DNA binding affinity of nuclear factor-κB (NF-κB). Ascochlorin down-regulates phospho-extracellular signal-regulated kinase 1/2 (p-ERK1/2) and p-p38.

Cell Viability Assay

Cell Line: HepG2, HCCLM3, Huh7 cells
Concentration: 10, 25, 50 μM
Incubation Time: 24, 48, 72 hours
Result: Inhibit the viability of three different HCC cell lines tested (HepG2, HCCLM3 and Huh7) in a time and dose dependent manner.

Western Blot Analysis

Cell Line: HepG2 cells
Concentration: 50 μM
Incubation Time: 48 hours
Result: Inhibited expression of the cell cycle regulator protein cyclin D1, the anti-apoptotic proteins Bcl-2, Mcl-1, survivin and XIAP, and the invasive gene product MMP-9.
體內(nèi)研究

Ascochlorin (Ilicicolin D) (2.5-5 mg/kg; i.p.; day 0, 1, 2, 3, 13, 15, 17, 20, 22, 24, 27, 29 and 31) inhibits tumor growth in an orthotopic HCC mouse model.

Animal Model: Eight week-old athymic balb/c nude female mice (HCCLM3-Luc2 tumors)
Dosage: 2.5 mg/kg, 5 mg/kg
Administration: I.p.; day 0, 1, 2, 3, 13, 15, 17, 20, 22, 24, 27, 29 and 31
Result: Induced significant inhibition of tumor growth.
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