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乙氧基喹啉

乙氧基喹啉用途

Ethoxyquin 是一种多年来用于动物饲料的抗氧化剂,也是热休克蛋白 90 (Hsp90) 的抑制剂。

乙氧基喹啉名称

[ CAS 号 ]:
91-53-2

[ 中文名 ]:
乙氧喹啉

[ 英文名 ]:
Ethoxyquin

[中文别名 ]:

[英文别名 ]:

6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline
Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-
EINECS 202-075-7
6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline
emq
quinoled
UNII-9T1410R4OR
2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline
nocracaw
amea100

乙氧基喹啉生物活性

[ 描述 ]:

Ethoxyquin 是一种多年来用于动物饲料的抗氧化剂,也是热休克蛋白 90 (Hsp90) 的抑制剂。

[ 相关类别 ]:

研究领域 >> 癌症

[ 靶点 ]

HSP90

[体外研究]

Ethoxyquin(EQ)不会阻断紫杉醇(PTX)在4种不同乳腺癌细胞系中诱导细胞死亡的能力。结果表明,只有当Hsp90水平下调时,由Ethoxyquin(EQ)提供的神经保护作用才会被发现[2]。发现Ethoxyquin提供神经保护,最佳功效范围为30至300 nM。有趣的是,较高(μM)浓度的乙氧基喹不能提供进一步的神经保护作用,实际上在这些较高浓度下,Ethoxyquin失去其神经保护作用[3]。

[体内研究]

Ethoxyquin(EQ)提供剂量依赖性神经保护作用。尽管所有3剂乙氧喹都能提供部分神经保护作用,以防止表皮内神经纤维密度降低,但峰值疗效为75μg/ kg剂量[2]。单独使用Ethoxyquin(EQ)或对照载体治疗的大鼠治疗的大鼠在正常生理条件下如预期的那样增重[3]。

[激酶实验]

为了评估Ethoxyquin（EQ）对紫杉醇（PTX）杀死乳腺癌细胞的能力的影响，针对96孔板形式优化培养4种癌细胞系和测量ATP水平的条件。简而言之，将1,500个细胞/孔的培养基接种在96孔板中24小时。将含有或不含有乙氧基喹啉的恒定浓度的PTX再加入孔中24小时。根据制造商的协议[2]，使用试剂盒测量细胞ATP水平。

[细胞实验]

简而言之，根据标准方案从胚胎第14.5天大鼠收获DRG，然后将细胞接种到胶原蛋白包被的玻璃盖玻片上并使神经突在培养基中延伸24小时（Neurobasal培养基，50mM青霉素 - 链霉素（PS），0.2％ FBS，0.5mM谷氨酰胺，1×B-27补充剂，0.2％葡萄糖，10ng / mL神经胶质细胞系衍生的神经营养因子）。将Ethoxyquin（EQ）或载体对照加入孔中再孵育24小时。用4％多聚甲醛固定DRG细胞，并用抗βIII-微管蛋白抗体染色以描绘轴突。轴突长度使用随机抽样方法在多个场中测量[2]。

[动物实验]

为了研究乙氧喹（EQ）对紫杉醇（PTX）减少体内肿瘤负荷的能力的影响，一种小鼠模型，其中乳腺癌细胞系SUM-159（3×106肿瘤细胞在最终体积中悬浮于磷酸盐缓冲盐水中）将0.15mL）皮下注射到成年雄性裸鼠中。当肿瘤直径达到5mm时，将动物随机分配到具有乙氧基喹啉基团的PTX或PTX。乙氧喹通过腹膜内给药每天给药3周。在3周结束时，对动物实施安乐死并测量肿瘤大小和重量（每组n = 5）[2]。

[参考文献]

[1]. Sadikot T, et al. Development of a high-throughput screening cancer cell-based luciferase refolding assay for identifying Hsp90 inhibitors. Assay Drug Dev Technol. 2013 Oct;11(8):478-88.

[2]. Zhu J, et al. Ethoxyquin prevents chemotherapy-induced neurotoxicity via Hsp90 modulation. Ann Neurol. 2013 Dec;74(6):893-904.

[3]. Zhu J, et al. Ethoxyquin provides neuroprotection against cisplatin-induced neurotoxicity. Sci Rep. 2016 Jun 28;6:28861.

[相关活性小分子]

乙氧基喹啉物理化学性质

[ 密度 ]:
1.0±0.1 g/cm3

[ 沸点 ]:
333.1±42.0 °C at 760 mmHg

[ 熔点 ]:
<0ºC

[ 分子式 ]:
C₁₄H₁₉NO

[ 分子量 ]:
217.307

[ 闪点 ]:
137.8±17.3 °C

[ 精确质量 ]:
217.146667

[ PSA ]:
21.26000

[ LogP ]:
3.93

[ 外观性状 ]:
黄色至红色-棕色液体

[ 蒸汽压 ]:
0.0±0.7 mmHg at 25°C

[ 折射率 ]:
1.512

[ 储存条件 ]:
库房低温,通风,干燥,防火,与氧化剂,食品原料分开存放

[ 稳定性 ]:
Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air.

[ 水溶解性 ]:
ethanol: 50 mL/L, clear, brown | <0.1 g/100 mL at 20 ºC

乙氧基喹啉MSDS

详细MSDS(安全技术说明书)

乙氧基喹啉毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VB8225000

CHEMICAL NAME :: Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-

CAS REGISTRY NUMBER :: 91-53-2

LAST UPDATED :: 199710

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C14-H19-N-O

MOLECULAR WEIGHT :: 217.34

WISWESSER LINE NOTATION :: T66 BM CHJ C1 C1 E1 HO2

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 :: 800 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 :: Rodent - mouse

DOSE/DURATION :: 1730 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 178 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Behavioral - coma

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 14377 mg/kg/3W-C

TOXIC EFFECTS :: Blood - change in clotting factors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 63 gm/kg/30W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in bladder weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 122 gm/kg/58W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12 gm/kg/29W-C

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 13 gm-kg/4W (Continuous)

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 99,37,1989 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83809 No. of Facilities: 204 (estimated) No. of Industries: 3 No. of Occupations: 13 No. of Employees: 3572 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83809 No. of Facilities: 876 (estimated) No. of Industries: 6 No. of Occupations: 14 No. of Employees: 7945 (estimated)

乙氧基喹啉安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

[ 警示性声明 ]:
P301 + P312 + P330

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
S24

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

[ WGK德国 ]:
1

[ RTECS号 ]:
VB8225000

[ 海关编码 ]:
2933499090

乙氧基喹啉合成路线

详细合成路线

乙氧基喹啉上下游产品

乙氧基喹啉上游产品

乙氧基喹啉下游产品

乙氧基喹啉制备

1.由对氨基苯乙醚与丙酮缩合而得。在苯磺酸催化下，对氨基苯乙醚与丙酮在155-165℃进行缩合反应。反应生成的水和未反应的丙酮反回丙酮蒸发器回收使用。缩合反应后，蒸馏得到成品。也可以用1%碘和催化剂，在120-130℃进行缩合反应。原料消耗(kg/t)对氨基苯乙醚 1000丙酮 800苯磺酸 100

每吨产品消耗对氨基苯乙醚1000kg、丙酮800kg、苯磺酸100kg。工艺流
程如下：

也可以用1%的碘、浓盐酸、三氯化铝、溴化氢等作催化剂，在100～170℃进行缩合反应制备乙氧喹。

2.一般由对氨基苯乙醚与丙酮在催化剂作用下缩合而得。

3.在苯磺酸催化下，对氨基苯乙醚与丙酮进行缩合反应制得。

乙氧基喹啉海关

[ 海关编码 ]: 2933499090

[ 中文概述 ]:
2933499090. 其他含喹琳或异喹啉环系的化合物〔但未进一步稠合的〕. 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 ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

乙氧基喹啉文献

Modulation of ethoxyquin genotoxicity by free radical scavengers and DNA damage repair in human lymphocytes.

Toxicol. Lett. 193(2) , 194-9, (2010)

N-tert-butyl-alpha-phenylnitrone (PBN) and its new derivative N-(Pyridine-4-ylmethylidene)-2-carboxy-tert-butylamine N-oxide (PBNC) were synthesized and used to modulate ethoxyquin (1,2-dihydro-6-etho...

Effects of a dietary antioxidant blend and vitamin E on fatty acid profile, liver function, and inflammatory response in broiler chickens fed a diet high in oxidants.

Poult. Sci. 93(7) , 1658-66, (2014)

The aim of the current study was to determine the effects of a dietary antioxidant blend and vitamin E on fatty acid profile, inflammatory response, and liver function. Cobb 500 male broilers (n = 1,2...

Effects of a dietary antioxidant blend and vitamin E on growth performance, oxidative status, and meat quality in broiler chickens fed a diet high in oxidants.

Poult. Sci. 93(7) , 1649-57, (2014)

The aim of the study was to determine the effects of a dietary antioxidant blend (AB) and vitamin E on performance, oxidative status, and meat quality. Cobb 500 male broilers (n = 1,200, d 0) were ran...

更多文献