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5-(十四烷基氧)-2-糠酸

5-(十四烷基氧)-2-糠酸用途

TOFA (RMI14514;MDL14514)是乙酰辅酶A羧化酶-α (ACCA )的变构抑制剂。

5-(十四烷基氧)-2-糠酸名称

[ CAS 号 ]:
54857-86-2

[ 中文名 ]:
5-(十四烷基氧)-2-糠酸

[ 英文名 ]:
TOFA

[英文别名 ]:

5-Tetradecyloxy-2-furonic acid
TOFA
2-Furancarboxylic acid, 5-(tetradecyloxy)-
5-tetradecoxyfuran-2-carboxylic acid
5-(Tetradecyloxy)-2-furoic acid
MFCD01726059

5-(十四烷基氧)-2-糠酸生物活性

[ 描述 ]:

TOFA (RMI14514;MDL14514)是乙酰辅酶A羧化酶-α (ACCA )的变构抑制剂。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> 乙酰辅酶A羧化酶

研究领域 >> 癌症

[体外研究]

TOFA(5-十四烷氧基-2-糠酸)对肺癌细胞NCI-H460和结肠癌细胞HCT-8和HCT-15具有细胞毒性,IC50分别为约5.0,5.0和4.5μg/ mL。 TOFA在1.0-20.0μg/ mL时有效阻断脂肪酸合成并以剂量依赖性方式诱导细胞死亡[1]。发现TOFA对COC1和COC1/DDP细胞具有细胞毒性,IC50值分别为~26.1和11.6μg/ mL。 TOFA以时间和剂量依赖的方式抑制检测的癌细胞的增殖,阻止细胞进入G0/G1细胞周期阶段并诱导细胞凋亡[2]。乙酰辅酶A羧化酶-α(ACCA)是调节脂肪酸合成的关键酶。 TOFA对ACCA的抑制降低了大多数PCa细胞系中脂肪酸合成并诱导caspase活化和细胞死亡[3]。

[体内研究]

TOFA抑制卵巢肿瘤小鼠异种移植物中的COC1/DDP细胞生长。与DMSO处理的对照小鼠相比,TOFA显着抑制肿瘤生长速率(1649±356.3对比5128±390.4 mm3。在心脏,肝脏,脾脏,肺脏,肾脏和肠道组织中未观察到毒性。通过抑制ACC,TOFA可能是一种很有前景的卵巢癌治疗小分子药物[2]。

[细胞实验]

将NCI-H460，人肺癌细胞和HCT-8和HCT-15细胞（5,000 /孔）接种于96孔板中过夜，然后暴露于指定浓度的TOFA（0,1,5,10,20， 50μg/ mL）72小时。使用MTT测定法检测活细胞[1]。

[动物实验]

小鼠：用50μLDMSO（对照组）处理小鼠或用TOFA（50mg / kg）处理。每天腹腔注射药物两周。通过用游标卡尺测量尺寸（长度和宽度），每两天记录肿瘤体积。最后一次治疗后四周处死小鼠。通过量表[2]测量肿瘤重量。

[参考文献]

[1]. Wang C, et al. Acetyl-CoA carboxylase-alpha inhibitor TOFA induces human cancer cell apoptosis. Biochem Biophys Res Commun. 2009 Jul 31;385(3):302-6.

[2]. Li S, et al. TOFA suppresses ovarian cancer cell growth in vitro and in vivo. Mol Med Rep. 2013 Aug;8(2):373-8.

[3]. Guseva NV, et al. TOFA (5-tetradecyl-oxy-2-furoic acid) reduces fatty acid synthesis, inhibits expression of AR, neuropilin-1 and Mcl-1 and kills prostate cancer cells independent of p53 status. Cancer Biol Ther. 2011 Jul 1;12(1):80-5.

[相关活性小分子]

Firsocostat | ND-646 | 盐酸CP-640186 | PF-05175157 | 格奥卢司他 | MK-4074

5-(十四烷基氧)-2-糠酸物理化学性质

[ 密度 ]:
1.0±0.1 g/cm3

[ 沸点 ]:
441.7±25.0 °C at 760 mmHg

[ 熔点 ]:
112-115ºC

[ 分子式 ]:
C₁₉H₃₂O₄

[ 分子量 ]:
324.455

[ 闪点 ]:
220.9±23.2 °C

[ 精确质量 ]:
324.230072

[ PSA ]:
59.67000

[ LogP ]:
7.82

[ 蒸汽压 ]:
0.0±1.1 mmHg at 25°C

[ 折射率 ]:
1.483

[ 储存条件 ]:
2-8℃

5-(十四烷基氧)-2-糠酸MSDS

详细MSDS(安全技术说明书)

5-(十四烷基氧)-2-糠酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LU0288000

CHEMICAL NAME :: 2-Furancarboxylic acid, 5-(tetradecyloxy)-

CAS REGISTRY NUMBER :: 54857-86-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C19-H32-O4

MOLECULAR WEIGHT :: 324.51

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 :: >5 gm/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - somnolence (general depressed activity)

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18200 mg/kg/26W-C

TOXIC EFFECTS :: Liver - changes in liver weight

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

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

TOXIC EFFECTS :: Liver - changes in liver weight

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981

5-(十四烷基氧)-2-糠酸安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

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

[ 海关编码 ]:
2932190090

5-(十四烷基氧)-2-糠酸合成路线

详细合成路线

5-(十四烷基氧)-2-糠酸上下游产品

5-(十四烷基氧)-2-糠酸上游产品

5-(十四烷基氧)-2-糠酸下游产品

5-(十四烷基氧)-2-糠酸海关

[ 海关编码 ]: 2932190090

[ 中文概述 ]:
2932190090 其他结构上有非稠合呋喃环化合物. 增值税率:17.0% 退税率:9.0% 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

[ Summary ]:
2932190090 other compounds containing an unfused furan ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

5-(十四烷基氧)-2-糠酸文献

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PLoS Pathog. 10(3) , e1004021, (2014)

The poxvirus life cycle, although physically autonomous from the host nucleus, is nevertheless dependent upon cellular functions. A requirement for de novo fatty acid biosynthesis was implied by our p...

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