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3,3,5,5-四碘甲腺乙酸

3,3,5,5-四碘甲腺乙酸

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?3,3,5,5-四碘甲腺乙酸名称
















中文名

3,3,5,5-四碘甲腺乙酸
英文名

2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid
英文别名
更多





?3,3,5,5-四碘甲腺乙酸生物活性












































描述
Tetrac (Tetraiodothyroacetic acid)，L-甲状腺素 (T4) 的脱氨基类似物，是甲状腺素整合素受体拮抗剂。Tetrac 阻断 T3 和 T4 的作用以及不同的生长因子介导的血管生成。Tetra 还具有抗肿瘤活性。
相关类别


体外研究

四环素（0.01-1μM；2-6d）诱导不同K-RAS状态的HT-29和HCT116细胞的抗增殖作用[3]。四环素（0.1μM；30min）抑制HT-29和HCT116细胞中ERK1/2的激活[3]。四环素（0.1μM；24h）抑制CCND1和c-Myc的表达，但促进CASP2和THBS1的表达[3]。细胞增殖试验[3]细胞系：HT-29和HCT116细胞浓度：0.01、0.1、1μM孵育时间：0、2、4、6d结果：诱导K-RAS野生型大肠癌细胞增殖。Western Blot分析[3]细胞株：HT-29和HCT116细胞浓度：0.1μM孵育时间：30min结果：抑制组成性激活的ERK1/2，这种抑制作用可通过抗整合素αvβ3抗体预处理而消除。
体内研究

四环素（35μg；p.o.40天）抑制小鼠肿瘤接种、生长和整合素表达[4]。动物模型：8周龄野生型雄性Balb/C小鼠接种102B16F10或B16LS9细胞[4]剂量：35μg/天给药：P.o.（加饮用水中）连续40天。结果：延缓了眼部黑色素瘤的发病。降低B16F10小鼠模型的S-100和整合素染色水平。
溶解度

In Vitro:

DMSO : 100 mg/mL (133.72 mM; Need ultrasonic)

In Vivo:

1.

请依序添加每种溶剂：?10% DMSO ?? 40% PEG300 ?? 5% Tween-80 ?? 45% saline

Solubility: 2.5 mg/mL (3.34 mM); Suspended solution; Need ultrasonic

2.

请依序添加每种溶剂：?10% DMSO ?? 90% (20% SBE-β-CD in saline)

Solubility: ≥ 2.5 mg/mL (3.34 mM); Clear solution

3.

请依序添加每种溶剂：?10% DMSO ?? 90% corn oil

Solubility: ≥ 2.5 mg/mL (3.34 mM); Clear solution
储备液

1 mM 1.3372 mL 6.6860 mL 13.3720 mL
5 mM 0.2674 mL 1.3372 mL 2.6744 mL
10 mM 0.1337 mL 0.6686 mL 1.3372 mL


运输

室温
SMILES

O=C(O)CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1
参考文献

[1]. Schmohl KA, et, al. Tetrac as an anti-angiogenic agent in cancer. Endocr Relat Cancer. 2019 Jun 1; 26(6):R287-R304.

[2]. Davis PJ, et, al. Nongenomic Actions of Thyroid Hormone: the Integrin Component. Physiol Rev. 2020 Jun 25.

[3]. Chin YT, et, al. Tetrac and NDAT Induce Anti-proliferation via Integrin αvβ3 in Colorectal Cancers With Different K-RAS Status. Front Endocrinol (Lausanne). 2019 Mar 12; 10:130.

[4]. Ashur-Fabian O, et, al. Tetrac Delayed the Onset of Ocular Melanoma in an Orthotopic Mouse Model. Front Endocrinol (Lausanne). 2019 Jan 8; 9:775.

[5]. Rajabi M, et, al. Synthesis of new analogs of tetraiodothyroacetic acid (tetrac) as novel angiogenesis inhibitors for treatment of cancer. Bioorg Med Chem Lett. 2018 Apr 15;28(7):1223-1227.






?3,3,5,5-四碘甲腺乙酸物理化学性质









































密度 2.727g/cm3
沸点 544.8?C at 760 mmHg
熔点 230 °C
分子式 C14H8I4O4
分子量 747.82900
闪点 283.3?C
精确质量 747.66000
PSA 66.76000
LogP 5.23000
外观性状 固体;White to Yellow to Green powder to crystal
折射率 1.801
储存条件 <0°C;避免加热






?3,3,5,5-四碘甲腺乙酸安全信息




































符号

GHS06


GHS06
信号词
Danger
危害声明
H300
警示性声明
P264-P301 + P310
个人防护装备
Eyeshields;Faceshields;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)
T+
风险声明 (欧洲)
28
安全声明 (欧洲)
45
危险品运输编码 UN 2811 6.1/PG 1
RTECS号 CY1585800
海关编码 2918990090





?3,3,5,5-四碘甲腺乙酸合成线路



































3,5-二碘-THYRO乙酸结构式

3,5-二碘-THYRO乙酸

1155-40-4




~90%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：Bridoux, Alexandre; Khan, Riaz A.; Chen, Celei; Cheve, Gwenael; Cui, Huadong; Dyskin, Evgeny; Yasri, Aziz; Mousa, Shaker A. Journal of Enzyme Inhibition and Medicinal Chemistry, 2011 , vol. 26, # 6 p. 871 – 882





(4-hydroxy-3,5-dinitro-phenyl)-acetic acid ethyl ester结构式

(4-hydroxy-3,5-…

83799-60-4




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：US2011/105482 A1, ;





[4-(4-methoxy-phenoxy)-3,5-dinitro-phenyl]-acetic acid ethyl ester结构式

[4-(4-methoxy-p...

861065-72-7




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：US2011/105482 A1, ;





4-甲氧基苯酚(MEHQ)结构式

4-甲氧基苯酚(MEHQ)

150-76-5




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：US2011/105482 A1, ;





ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate结构式

ethyl 3,5-diiod...

85828-82-6




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：Biochemical Journal, , vol. 63, p. 601,603





ethyl 2-(3,5-diamino-4-(4-methoxyphenoxy)phenyl)acetate结构式

ethyl 2-(3,5-di...

101588-11-8




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：US2011/105482 A1, ;





1-(4-chloromethyl-2,6-diiodo-phenoxy)-4-methoxy-benzene结构式

1-(4-chlorometh...

860687-73-6




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：Biochemical Journal, , vol. 50, p. 438




[3,5-diiodo-4-(...

855937-68-7




~%







3,3,5,5-四碘甲腺乙酸结构式

3,3,5,5-四碘甲腺乙酸

67-30-1


文献：Biochemical Journal, , vol. 50, p. 438















?3,3,5,5-四碘甲腺乙酸海关















海关编码 2918990090
中文概述 2918990090. 其他含其他附加含氧基羧酸（包括酸酐、酰卤化物、过氧化物和过氧酸及该税号的衍生物）. 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:30.0%
申报要素 品名, 成分含量, 用途
Summary 2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%








?3,3,5,5-四碘甲腺乙酸文献28

更多文献







Tetraiodothyroacetic acid-tagged liposomes for enhanced delivery of anticancer drug to tumor tissue via integrin receptor

J. Control. Release 164(2) , 213-20, (2012)

Nanoparticles have demonstrated potential for promoting drug delivery to tumor sites and enhancing uptake. Here, we report tetraiodothyroacetic acid (tetrac) as a promising new targeting moiety for de…



Tetraiodothyroacetic acid and tetraiodothyroacetic acid nanoparticle effectively inhibit the growth of human follicular thyroid cell carcinoma.

Thyroid 20(3) , 281-6, (2010)

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