[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-

用途

Secalonic acid D是一种对肿瘤细胞具有毒性的化合物。Secalonic acid D可以从刺曲霉的代谢产物中分离出来。Secalonic acid D激活GSK3-β,并降解β-连环蛋白。因此,Secalonic acid D下调c-Myc的表达,将细胞周期阻滞在G1期,诱导细胞凋亡[1][2]。
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名称

[ CAS 号 ]:
35287-69-5

[ 英文名 ]:
[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-

[英文别名 ]:

生物活性

[ 描述 ]:

Secalonic acid D是一种对肿瘤细胞具有毒性的化合物。Secalonic acid D可以从刺曲霉的代谢产物中分离出来。Secalonic acid D激活GSK3-β,并降解β-连环蛋白。因此,Secalonic acid D下调c-Myc的表达,将细胞周期阻滞在G1期,诱导细胞凋亡[1][2]。

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 细胞凋亡
信号通路 >> 干细胞及 Wnt 通路 >> GSK-3
研究领域 >> 癌症
信号通路 >> 细胞凋亡 >> c-Myc的
信号通路 >> PI3K/Akt/mTOR 信号通路 >> GSK-3

[体外研究]

司卡隆酸D(0.1-1μM；72小时)在 HL60型和 K562细胞中以浓度依赖性方式抑制细胞增殖,IC50型分别为 0.38微米和 0.43微米[1]癸酸D(0.3μM；12小时,24小时)导致细胞周期停滞在 G1期,(1.2μM；0-72小时)并诱导 HL60型和 K562细胞细胞凋亡[1]。 细胞凋亡分析[1]细胞系：HL60和K562细胞浓度：1.2μM培养时间：0、24、48和72小时结果：通过将细胞周期阻滞在G1期诱导细胞凋亡。以及下调c-Myc的表达水平。Western印迹分析[1]细胞系：HL60和K562细胞浓度：1.2μM孵育时间：0、24、48和72小时结果：Caspase-1水平呈剂量依赖性降低。

[参考文献]

[1]. Andersen R, et al. Secalonic acids D and F are toxic metabolites of Aspergillus aculeatus. J Org Chem. 1977 Jan 21;42(2):352-3.  

[2]. Zhang JY, et al. Secalonic acid D induced leukemia cell apoptosis and cell cycle arrest of G(1) with involvement of GSK-3beta/beta-catenin/c-Myc pathway. Cell Cycle. 2009 Aug;8(15):2444-50.  

物理化学性质

[ 密度 ]:
1.67g/cm3

[ 沸点 ]:
846ºC at 760 mmHg

[ 分子式 ]:
C32H30O14

[ 分子量 ]:
638.57200

[ 闪点 ]:
273.7ºC

[ 精确质量 ]:
638.16400

[ PSA ]:
226.58000

[ LogP ]:
2.16420

[ 折射率 ]:
1.725

毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EC2460000
CHEMICAL NAME :
(7,7'-Bi-4aH-xanthene)-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8, 8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, (3S-(3-alpha,4-beta,4a-beta, 7(3'R,4'S,4'aS)))
CAS REGISTRY NUMBER :
35287-69-5
LAST UPDATED :
199609
DATA ITEMS CITED :
17
MOLECULAR FORMULA :
C32-H30-O14
MOLECULAR WEIGHT :
638.62

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - hepatitis (hepatocellular necrosis), zonal Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - hepatitis (hepatocellular necrosis), zonal Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
26500 ug/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Lungs, Thorax, or Respiration - changes in pulmonary vascular resistance Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Skin and Appendages - hair
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg/5D-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - chronic pulmonary edema Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - respiratory system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
15 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
15 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - gastrointestinal system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
25 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical Reproductive - Effects on Newborn - delayed effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
lactating female 10 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
45 mg/kg
SEX/DURATION :
female 7-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
30 mg/kg
REFERENCE :
JEPTDQ Journal of Environmental Pathology and Toxicology. (Park Forest South, IL) V.1-5(3), 1977-81(?). For publisher information, see JEPOEC. Volume(issue)/page/year: 4(5-6),31,1980
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安全信息

[ 危害码 (欧洲) ]:
T+

[ 风险声明 (欧洲) ]:
28

[ 危险品运输编码 ]:
UN 2811 6.1/PG 2

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相关化合物

CAS号[35287-69-5]化源网提供[[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-]MSDS、说明、性质、英文名、生产厂家、作用/用途、分子量、密度、沸点、熔点、结构式等。>>电脑版：[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-

标题：【[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-】[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)- CAS号:35287-69-5【结构式 性质 活性】-化源网 地址：https://m.chemsrc.com/mip/cas/35287-69-5_840661.html