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5-氨基水杨酸

5-氨基水杨酸用途

5-Aminosalicylic acid 是一种特异性的 PPARγ 激动剂,还抑制 p21-激活激酶1 (PAK1) 和 NF-κB。

5-氨基水杨酸名称

[ CAS 号 ]:
89-57-6

[ 中文名 ]:
美沙啦嗪(5-氨基水杨酸)

[ 英文名 ]:
5-Aminosalicylic Acid

[中文别名 ]:

[英文别名 ]:

5-Aminosalicylic Acid
Mesalamine
5-AMINOSALICILIC ACID
5-AMINO SALICYLIC ACID
Mesalamine (Lialda)
Bactylan
Pasalon-rakeet
5-amino-2-hydroxybenzoic acid
Tubersan
Salvis

5-氨基水杨酸生物活性

[ 描述 ]:

5-Aminosalicylic acid 是一种特异性的 PPARγ 激动剂,还抑制 p21-激活激酶1 (PAK1) 和 NF-κB。

[ 相关类别 ]:

信号通路 >> 细胞周期/DNA损伤 >> PAK

信号通路 >> 细胞骨架 >> PAK

研究领域 >> 炎症/免疫

[ 靶点 ]

PPARγ

PAK1

p65

[体外研究]

5-氨基水杨酸(5-ASA)是PPARγ的特异性激动剂,只有PPARγ而非PPARα或PPARδ诱导p65降解。 5-氨基水杨酸诱导p65蛋白的降解,表明PPARγ的E3泛素连接酶活性。 5-氨基水杨酸还在mRNA水平抑制PAK1,这暗示了独立于PPARγ配体激活的另外机制。 5-氨基水杨酸通过抑制PAK1阻断肠上皮细胞(IECs)中的NF-κB[1]。用不同浓度(10-1000μmol/ L)的5-氨基水杨酸(5-ASA)或尼美舒利预处理12-96小时,以剂量和时间依赖的方式抑制HT-29结肠癌细胞的生长。然而,5-氨基水杨酸或尼美舒利的抑制没有统计学意义。当用不同剂量的5-氨基水杨酸和尼美舒利预处理时,HT-29结肠癌细胞的生长受到剂量依赖性的抑制。组合的5-氨基水杨酸(终浓度100μM)和尼美舒利(终浓度10-1000μM)以剂量依赖性方式抑制HT-29结肠癌细胞的增殖,比相应剂量的尼美舒利更有效。类似地,组合尼美舒利(终浓度100μM)和5-氨基水杨酸(终浓度10-1000μM)也剂量依赖性地抑制这些细胞的增殖,比相应剂量的5-氨基水杨酸更有效[2]。

[体内研究]

5-氨基水杨酸(5-ASA)在异种移植肿瘤模型中具有抗肿瘤作用。为了评价5-氨基水杨酸的体内抗肿瘤作用,用50mM的5-氨基水杨酸每天处理植入HT-29结肠癌细胞的SCID小鼠连续21天。在治疗结束时,与仅用GW9662治疗的对照小鼠或小鼠相比,在接受5-氨基水杨酸的SCID小鼠中观察到肿瘤重量和体积减少80-86％。在5-氨基水杨酸处理10天后,已经可检测到5-氨基水杨酸的抗肿瘤作用。用5mM的5-氨基水杨酸处理的小鼠获得了类似的结果。通过同时腹膜内施用GW9662,在21天完全消除5-氨基水杨酸的抗肿瘤发生作用。因此,观察到的5-氨基水杨酸的抗肿瘤作用至少部分依赖于PPARγ[3]。

[细胞实验]

通过MTT测定法测量细胞抑制效应。用0.25％胰蛋白酶溶液分离HT-29结肠癌细胞5分钟。随后，将细胞接种到96孔板（1×106细胞/孔）上，补充10％FCS并使其附着24小时，然后加入试验化合物（5-氨基水杨酸10,50,100,500），和1000μM;尼美舒利;和它们的组合）。将测试化合物在无血清培养基中稀释。然后将细胞在培养基或不同浓度的药物中孵育48小时，加入20μL在PBS中的MTT溶液（5g / L）。 4小时后，除去各孔中的培养基，加入120μL0.04mM盐酸异丙醇，稍微浓缩10分钟。用ELISA读数器在490nm处测量染料吸收。每个浓度使用5个孔或作为对照组。另一方面，将细胞接种到96孔板（1×10 6个细胞/孔）上并使其附着24小时，然后用试验化合物（5-氨基水杨酸，尼美舒利及它们的组合）处理。最终浓度为100μM。将相同的培养基加入对照组中，然后测量染料摄取。每个测试化合物或对照组使用5个孔[2]。

[动物实验]

小鼠[3]使用6至7周龄无病原体的BALB / c SCID小鼠。将用GW9662预处理或不处理24小时的人结肠癌细胞（107 HT-29细胞）皮下植入动物的侧腹。细胞接种后两天，通过瘤周注射每天施用5-氨基水杨酸（5或50mM）处理小鼠10或21天。通过每日腹膜内注射GW9662（1mg / kg /天）评估PPARγ在5-氨基水杨酸处理期间的作用。对照组接受盐水而不是5-氨基水杨酸。每周检查小鼠三次以进行肿瘤发展。在10或21天杀死后，计算肿瘤大小和体积。在石蜡包埋之前对肿瘤进行加权以进行组织学检查。

[参考文献]

[1]. Dammann K, et al. PAK1 modulates a PPARγ/NF-κB cascade in intestinal inflammation. Biochim Biophys Acta. 2015 Oct;1853(10 Pt A):2349-60.

[2]. Fang HM, et al. 5-aminosalicylic acid in combination with Nimesulide inhibits proliferation of colon carcinoma cells in vitro. World J Gastroenterol. 2007 May 28;13(20):2872-7.

[3]. Rousseaux C, et al. The 5-aminosalicylic acid antineoplastic effect in the intestine is mediated by PPARγ. Carcinogenesis. 2013 Nov;34(11):2580-6.

[相关活性小分子]

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5-氨基水杨酸物理化学性质

[ 密度 ]:
1.5±0.1 g/cm3

[ 沸点 ]:
380.8±32.0 °C at 760 mmHg

[ 熔点 ]:
275-280 °C (dec.)(lit.)

[ 分子式 ]:
C₇H₇NO₃

[ 分子量 ]:
153.135

[ 闪点 ]:
184.1±25.1 °C

[ 精确质量 ]:
153.042587

[ PSA ]:
83.55000

[ LogP ]:
1.14

[ 外观性状 ]:
白色至灰白色粉末

[ 蒸汽压 ]:
0.0±0.9 mmHg at 25°C

[ 折射率 ]:
1.691

[ 储存条件 ]:
库房通风低温干燥

[ 水溶解性 ]:
<0.1 g/100 mL at 21 ºC

5-氨基水杨酸MSDS

详细MSDS(安全技术说明书)

5-氨基水杨酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VO1400000

CHEMICAL NAME :: Salicylic acid, 5-amino-

CAS REGISTRY NUMBER :: 89-57-6

BEILSTEIN REFERENCE NO. :: 2090421

LAST UPDATED :: 199710

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C7-H7-N-O3

MOLECULAR WEIGHT :: 153.15

WISWESSER LINE NOTATION :: ZR DQ CVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 6857 mg/kg/17W-I

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Liver - jaundice, cholestatic

REFERENCE :: JOHEEC Journal of Hepathology. (Elsevier Science, 655 Avenue of the Americas, New York, NY 10010) V.1- 1985- Volume(issue)/page/year: 26,425,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 21800 mg/kg/39W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - respiratory depression Blood - eosinophilia

REFERENCE :: AJGAAR American Journal of Gastroenterology. (American College of Gastroenterology, Inc., 428 E. Preston St., Baltimore, MD 21202) V.21- 1954- Volume(issue)/page/year: 91,1039,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 51 mg/kg/5D-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,917,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 8 mg/kg

TOXIC EFFECTS :: Behavioral - headache Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - body temperature increase

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,917,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 2057 mg/kg/17W-I

TOXIC EFFECTS :: Blood - agranulocytosis Nutritional and Gross Metabolic - body temperature increase

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 341,1476,1993

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2800 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - other changes

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570511

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Kidney, Ureter, Bladder - other changes in urine composition Skin and Appendages - hair

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 47,505,1994

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

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

REFERENCE :: ZENBAX Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie. (Tuebingen, Fed. Rep. Ger.) V.2B-27B, 1947-1972. For publisher information, see ZNCBDA. Volume(issue)/page/year: 6B,183,1951

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 681 mg/kg

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

REFERENCE :: PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 64,247,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - hematuria

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 47,509,1994

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570511 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 36400 mg/kg/13W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 48,277,1994

5-氨基水杨酸安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319-H335

[ 警示性声明 ]:
P261-P305 + P351 + P338

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

[ 危害码 (欧洲) ]:
Xi

[ 风险声明 (欧洲) ]:
36/37/38

[ 安全声明 (欧洲) ]:
S26-S36-S24/25

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

[ WGK德国 ]:
2

[ RTECS号 ]:
VO1400000

[ 海关编码 ]:
29225000

5-氨基水杨酸合成路线

详细合成路线

5-氨基水杨酸上下游产品

5-氨基水杨酸上游产品

5-氨基水杨酸下游产品

5-氨基水杨酸制备

方法1：水杨酸和水混合后，在50℃和搅拌下，缓慢滴加68%硝酸和冰醋酸的混合液。再升温至70～80℃反应。将反应液倾入水中，于5℃放置。过滤，滤饼用热水重结晶，得5-硝基水杨酸固体，收率40%。
在60℃，往盐酸溶液中加入铁粉。加热煮沸后，加入1/4的5-硝基水杨酸。剧烈搅拌后，将其余硝基物和铁粉分批交替加入。加毕，于102℃反应。趁热用50%氢氧化钠调至强碱性，过滤。滤饼用热水洗，滤液和洗液合并后，加入保险粉，用40%硫酸酸化至Ph值4。冷却，过滤，干燥，将其和亚硫酸氢钠溶于热水，和活性炭一起煮沸。热过滤，滤饼用少量热水洗。滤液和洗液合并，在5℃放置。滤集结晶，用冰水充分洗涤，干燥，得白色针状的美沙拉秦结晶，熔点278℃(分解)。

方法2：水杨酸经硝化得5-硝基水杨酸后，再和甲磺酰氯反应以对酚羟基进行保护，然后氢化还原硝基为氨基，最后水解得到美沙拉秦。

方法3：苯胺经重氮化得重氮盐，将其加入水杨酸、碳酸钠和40%氢氧化钠的溶液中，在0～6℃剧烈搅拌，并保持Ph值为8。过滤，饱和食盐水洗，压干。溶入40%氢氧化钠溶液，在80～85℃加入保险粉。待溶液完全褪色后，水蒸气蒸馏蒸除苯胺，过滤。滤液用浓盐酸调至Ph值6～6.5，放置过夜。过滤，冷水洗涤，干燥后的粗品溶于水，滴加浓盐酸至溶解，再加入活性炭，加热至沸。过滤，冷却，用稀氢氧化钠调至Ph值2～3。过滤，冷水洗涤，常温真空干燥，得灰白色的美沙拉秦固体，熔点278℃(分解)，总收率45.9%。

方法4：对氨基苯酚和适量催化剂，在2.0～3.0MPa的CO2压力和130～190℃下搅拌。冷至室温，加入水和保险粉，搅拌。冷至0～3℃，滤去不溶物，水洗。洗液和滤液合并，用盐酸调至Ph值3～4，过滤，水洗，得美沙拉秦粗品。向粗品加入水、碳酸氢钠和亚硫酸氢钠，热至50～60℃全溶后，加入活性炭煮沸。过滤，冷却，稀盐酸调至Ph值3.5。过滤，水洗，干燥，得灰白色的精品．收率91.1%，含量99.2%。

5-氨基水杨酸海关

[ 海关编码 ]: 2922509090

[ 中文概述 ]:
2922509090. 其他氨基醇酚、氨基酸酚及其他含氧基氨基化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件：AB. 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, 乙醇胺及其盐应报明色度, 乙醇胺及其盐应报明包装

[ 监管条件 ]: A.入境货物通关单 B.出境货物通关单

[ 检验检疫 ]: R.进口食品卫生监督检验 S.出口食品卫生监督检验

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

5-氨基水杨酸文献

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

Development and validation of an LC-MS/MS method for the determination of mesalazine in beagle dog plasma and its application to a pharmacokinetic study.

Biomed. Chromatogr. 29(2) , 261-7, (2015)

A simple, specific and sensitive LC-MS/MS method was developed and validated for the determination of mesalazine in beagle dog plasma. The plasma samples were prepared by protein precipitation, then t...

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