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3-吲哚甲醇

3-吲哚甲醇用途

Indole-3-carbinol 是芳烃受体 (AhR) 的激动剂。

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3-吲哚甲醇名称

[ CAS 号 ]:
700-06-1

[ 中文名 ]:
吲哚-3-甲醇

[ 英文名 ]:
Indole-3-carbinol

[中文别名 ]:

[英文别名 ]:

Indole-3-carbidol
MFCD02683932
3-INDOLAMETHANOL
3-indolemethanol
1H-Indole-3-methanol (9CI)
Indole-3-carbinol
EINECS 211-836-2
3-IndoleCarbinol
1H-Indol-3-ylmethanol
1H-Indole-3-methanol

3-吲哚甲醇生物活性

[ 描述 ]:

Indole-3-carbinol 是芳烃受体 (AhR) 的激动剂。

[ 相关类别 ]:

信号通路 >> 免疫及炎症 >> 芳基烃受体

天然产物 >> 生物碱

研究领域 >> 癌症

[ 靶点 ]

NF-κB

AhR

[体外研究]

发现吲哚-3-甲醇(I3C)以剂量和时间依赖性方式抑制THP-1细胞的增殖,对正常单核细胞的毒性最小。 AhR靶基因(CYP1A1,IL1β)在吲哚-3-甲醇处理后过表达(p <0.05至p <0.001)。吲哚-3-甲醇的抗增殖作用与编程细胞死亡有关。吲哚-3-甲醇下调BCL2并上调THP-1细胞中的FasR(p <0.05至p <0.001)。使用流式细胞术也观察到G1细胞周期停滞。 G1作用细胞周期基因(P21,P27和P53)过表达(p <0.05至p <0.001),而CDK2在吲哚-3-甲醇处理后下调(p <0.01至p <0.001)[1] .Indole -3-甲醇抑制NF-κB活性并刺激前B急性淋巴细胞白血病细胞中的p53通路[2]。

[细胞实验]

在含有5％CO 2的完全湿润的气氛中，在补充有10％FBS，100U / mL青霉素，100mg / mL链霉素和2mM Glutamax的RPMI 1640中培养THP-1细胞。将细胞（2-5×105mL-1）接种在六孔板中，然后重悬于完全生长培养基中。然后用10ng / mL佛波醇12-肉豆蔻酸酯13-乙酸酯作为肿瘤启动子处理THP-1单核细胞，以诱导稳定分化成附着的巨噬细胞样细胞和AhR的过表达。然后用不同浓度的吲哚-3-甲醇（1,10和100μM，和1mM）处理细胞。将THP-1细胞和富集的正常单核细胞以5×104个细胞/孔接种在具有不同浓度的吲哚-3-甲醇的24孔板中，观察24和48小时，然后进行MTT测定。将细胞一式三份孵育，最终体积为200mL无酚红RPMI 1640，持续20小时。将等份的20mL MTT溶液（5mg / mL）加入每个孔中并孵育4小时。形成Formazan晶体。然后将300mL DMSO的量作为细胞裂解溶液加入每个孔中。通过570nm处的分光光度法评估细胞活力的百分比[1]。

[参考文献]

[1]. Mohammadi S, et al. Indole-3-carbinol induces G1 cell cycle arrest and apoptosis through aryl hydrocarbon receptor in THP-1 monocytic cell line.J Recept Signal Transduct Res. 2017 Oct;37(5):506-514.

[2]. Safa M, et al. Indole-3-carbinol suppresses NF-κB activity and stimulates the p53 pathway in pre-B acute lymphoblastic leukemia cells. Tumour Biol. 2015 May;36(5):3919-30.

[相关活性小分子]

3-吲哚甲醇物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
360.6±17.0 °C at 760 mmHg

[ 熔点 ]:
96-99 °C(lit.)

[ 分子式 ]:
C₉H₉NO

[ 分子量 ]:
147.174

[ 闪点 ]:
171.9±20.9 °C

[ 精确质量 ]:
147.068420

[ PSA ]:
36.02000

[ LogP ]:
0.96

[ 外观性状 ]:
白色至灰白色晶体

[ 蒸汽压 ]:
0.0±0.8 mmHg at 25°C

[ 折射率 ]:
1.705

[ 储存条件 ]:
2-8°C

[ 稳定性 ]:
2-80C

[ 水溶解性 ]:
可溶于：甲醇

3-吲哚甲醇MSDS

详细MSDS(安全技术说明书)

3-吲哚甲醇毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL9483000

CHEMICAL NAME :: Indole-3-methanol

CAS REGISTRY NUMBER :: 700-06-1

BEILSTEIN REFERENCE NO. :: 0121323

LAST UPDATED :: 199706

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C9-H9-N-O

MOLECULAR WEIGHT :: 147.19

WISWESSER LINE NOTATION :: T56 BMJ D1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - coma

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 18,159,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 mg/kg/13W-I

TOXIC EFFECTS :: Liver - jaundice (or hyperbilirubinemia) hepatocellular Liver - changes in liver weight

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 15,292,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 5600 mg/kg/13W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 15,292,1995 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 mg/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - delayed effects

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 141,68,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 18,159,1980

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3-吲哚甲醇安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319

[ 警示性声明 ]:
P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/38

[ 安全声明 (欧洲) ]:
S26-S36

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
NL9483000

[ 海关编码 ]:
2933990090

3-吲哚甲醇合成路线

详细合成路线

3-吲哚甲醇上下游产品

3-吲哚甲醇上游产品

3-吲哚甲醇下游产品

3-吲哚甲醇海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3-吲哚甲醇文献

The extended version of restriction analysis approach for the examination of the ability of low-molecular-weight compounds to modify DNA in a cell-free system.

Food Chem. Toxicol. 75 , 118-27, (2015)

One of the primary requirements in toxicology is the assessment of ability of chemicals to induce DNA covalent modification. There are several well-established methods used for this purpose such as (3...

Indole-3-carbinol inhibits tumorigenicity of hepatocellular carcinoma cells via suppression of microRNA-21 and upregulation of phosphatase and tensin homolog.

Biochim. Biophys. Acta 1853(1) , 244-53, (2015)

A major obstacle to successful treatment of hepatocellular carcinoma (HCC) is its high resistance to cytotoxic chemotherapy due to overexpression of multidrug resistance genes. Activation of the AKT p...

In vitro activity of glucosinolates and their degradation products against brassica-pathogenic bacteria and fungi.

Appl. Environ. Microbiol. 81(1) , 432-40, (2014)

Glucosinolates (GSLs) are secondary metabolites found in Brassica vegetables that confer on them resistance against pests and diseases. Both GSLs and glucosinolate hydrolysis products (GHPs) have show...

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