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棉酚

棉酚用途

Gossypol 是一种从棉籽和根中分离出来的天然产物,分别与 Bcl-xL 蛋白和 Bcl-2 蛋白结合,Ki 值分别为 0.5-0.6 μM 和 0.2-0.3 mM。

棉酚名称

[ CAS 号 ]:
303-45-7

[ 中文名 ]:
棉酚

[ 英文名 ]:
Gossypol

[中文别名 ]:

棉子酚

[英文别名 ]:

MFCD00017352
Gossypol
gossypol from cotton seeds
Thespesin
roduct Name
(+/-)-gossypol

棉酚生物活性

[ 描述 ]:

Gossypol 是一种从棉籽和根中分离出来的天然产物,分别与 Bcl-xL 蛋白和 Bcl-2 蛋白结合,Ki 值分别为 0.5-0.6 μM 和 0.2-0.3 mM。

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> Bcl-2家族

研究领域 >> 癌症

天然产物 >> 酚类

[ 靶点 ]

Bcl-xL:0.5-0.6 μM (Ki)

Bcl-2:0.2-0.3 mM (Ki)

[体外研究]

棉酚,一种从棉籽和根中分离出来的天然产品,已被研究作为抗癌剂。外消旋形式的棉酚[(±)-棉酚]在几个临床试验中进行了测试,并且耐受性良好。外消旋形式Gossypol((±)-Gossypol)与Bcl-xL蛋白结合,Ki为0.5至0.6μM。 (±)-棉酚也有效结合Bcl-2蛋白,Ki值为0.2-0.3mM。天然外消旋棉酚具有两种对映体,即(-)-棉酚和(+)-棉酚对映体。在6天MTT测定中,针对UM-SCC-6和UM-SCC-14A测试外消旋形式和棉酚的每种对映体。 (-)-在所测试的两种细胞系中,棉酚相对于(±)-棉酚表现出比(+)-棉酚更大的生长抑制(P <0.001)。用(±)-Gossypol观察到中间生长抑制作用,但这种作用仅在较高剂量的棉酚(10μM,P <0.0001)[1]时观察到。

[细胞实验]

两种代表性的UM-SCC细胞系UM-SCC-6和UM-SCC-14A持续暴露于0（载体对照），5或10μM（±） - 棉酚，（ - ） - 棉酚或（+） - 棉酚在6天的MTT细胞存活试验中[1]。

[参考文献]

[1]. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63.

[相关活性小分子]

棉酚物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
707.9±55.0 °C at 760 mmHg

[ 熔点 ]:
181-183ºC

[ 分子式 ]:
C₃₀H₃₀O₈

[ 分子量 ]:
518.554

[ 闪点 ]:
395.9±28.0 °C

[ 精确质量 ]:
518.194092

[ PSA ]:
155.52000

[ LogP ]:
6.16

[ 外观性状 ]:
棕黄色粉末

[ 蒸汽压 ]:
0.0±2.3 mmHg at 25°C

[ 折射率 ]:
1.742

[ 储存条件 ]:
库房低温,通风,干燥,与食品原料分开存放

棉酚毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DU3100000

CHEMICAL NAME :: (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl- 3,3'-dimethyl-

CAS REGISTRY NUMBER :: 303-45-7

BEILSTEIN REFERENCE NO. :: 1917878

LAST UPDATED :: 199803

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C30-H30-O8

MOLECULAR WEIGHT :: 518.60

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 :: 2315 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - pig

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 17 mg/kg

SEX/DURATION :: male 60 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: male 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1050 mg/kg

SEX/DURATION :: male 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4500 mg/kg

SEX/DURATION :: male 90 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 525 mg/kg

SEX/DURATION :: male 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: male 70 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 10 mg/L/48H

REFERENCE :: ITCSAF In Vitro. (Rockville, MD) V.1-20, 1965-85. For publisher information, see ICDBEO. Volume(issue)/page/year: 19,53,1983

棉酚安全信息

[ 符号 ]:

GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H351

[ 警示性声明 ]:
P281

[ 个人防护装备 ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
Xn

[ 风险声明 (欧洲) ]:
R22;R40

[ 安全声明 (欧洲) ]:
S22-S36

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

[ WGK德国 ]:
3.0

[ RTECS号 ]:
DU3100000

棉酚合成路线

详细合成路线

棉酚上下游产品

棉酚上游产品

棉酚下游产品

棉酚文献

Male contraception: history and development.

Urol. Clin. North Am. 41(1) , 145-61, (2014)

Although the twentieth century has seen great strides in the development of female contraception, not a single new agent has been introduced as an approved method for common use for male contraception...

The investigational agent MLN2238 induces apoptosis and is cytotoxic to CLL cells in vitro, as a single agent and in combination with other drugs.

Br. J. Haematol. 165(1) , 78-88, (2014)

Chronic lymphocytic leukaemia (CLL) is the most common haematological malignancy in the U.S. The course of the disease has been shown to be negatively impacted by increased levels of BCL2. Strategies ...

(-)-Gossypol-enriched cottonseed oil inhibits proliferation and adipogenesis of human breast pre-adipocytes.

Anticancer Res. 33(3) , 949-55, (2013)

Breast cancer is the most commonly diagnosed cancer in women. Obesity is an important risk factor for developing breast cancer and is one of few risk factors that women can modify to prevent cancer. (...

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棉酚