26166-39-2

26166-39-2 structure

Name: Ascochlorin
Chemical Name: 5-chloro-2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde
CAS Number: 26166-39-2
Molecular Formula: C₂₃H₂₉ClO₄
Molecular Weight: 404.92700
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2017-08-13 13:43:07
Modify Date: 2024-01-11 11:44:07
Ascochlorin (Ilicicolin D), an isoprenoid antibiotic, mediates its anti-tumor effects predominantly through the suppression of STAT3 signaling cascade. Ascochlorin induces apoptosis. Anti-inflammatory activity[1][2][3].

Name	5-chloro-2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde
Synonyms	Ascochlorin Ilicicolin D ascochlorin

Description	Ascochlorin (Ilicicolin D), an isoprenoid antibiotic, mediates its anti-tumor effects predominantly through the suppression of STAT3 signaling cascade. Ascochlorin induces apoptosis. Anti-inflammatory activity[1][2][3].
Related Catalog	Signaling Pathways >> Stem Cell/Wnt >> STAT Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Signaling Pathways >> JAK/STAT Signaling >> STAT Research Areas >> Inflammation/Immunology
Target	STAT3 Apoptosis
In Vitro	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[3]. Ascochlorin (50 μM; 48 hours) induces apoptosis in HCC cells[3]. 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[2]. Cell Viability Assay[3] 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[3] 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.
In Vivo	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[1]. Animal Model: Eight week-old athymic balb/c nude female mice (HCCLM3-Luc2 tumors)[3] 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.
References	[1]. Min-Wen JC, et al. Molecular Targets of Ascochlorin and Its Derivatives for Cancer Therapy. Adv Protein Chem Struct Biol. 2017;108:199-225. [2]. Lee SH, et al. Anti-Inflammatory Effect of Ascochlorin in LPS-Stimulated RAW 264.7 Macrophage Cells Is Accompanied With the Down-Regulation of iNOS, COX-2 and Proinflammatory Cytokines Through NF-κB, ERK1/2, and p38 Signaling Pathway. J Cell Biochem. 2016 Apr;117(4):978-87. [3]. Dai X, et al. Ascochlorin, an isoprenoid antibiotic inhibits growth and invasion of hepatocellular carcinoma by targeting STAT3 signaling cascade through the induction of PIAS3. Mol Oncol. 2015 Apr;9(4):818-33.

Density	1.199g/cm3
Boiling Point	556.9ºC at 760mmHg
Molecular Formula	C₂₃H₂₉ClO₄
Molecular Weight	404.92700
Flash Point	290.6ºC
Exact Mass	404.17500
PSA	74.60000
LogP	5.55850
Vapour Pressure	5.2E-13mmHg at 25°C
Index of Refraction	1.603

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VH3707560

CHEMICAL NAME :: beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-ox ocyclohexyl)- 2,4-pentadienyl)-, (E,E)-

CAS REGISTRY NUMBER :: 26166-39-2

LAST UPDATED :: 199312

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C23-H29-Cl-O4

MOLECULAR WEIGHT :: 404.97

WISWESSER LINE NOTATION :: L6VTJ B1 C1U1Y1&U2R BQ FQ CG D1 EVH& E1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 21,539,1968

RIDADR	NONH for all modes of transport

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