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格尔德霉素

格尔德霉素用途

Geldanamycin是 Hsp90 抑制剂,具有抗许多革兰氏阳性和一些革兰氏阴性细菌的活性。

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格尔德霉素名称

[ CAS 号 ]:
30562-34-6

[ 中文名 ]:
格尔德霉素

[ 英文名 ]:
Geldanamycin

[中文别名 ]:

粉防己碱

[英文别名 ]:

GELDANAMYCIN,STREPTOMYCES HYGROSCOPICUS
Streptomyces hygroscopicus
GELDANAMYCIN FROM STRE
Geldanamycin
MFCD00274570
Geldanamycin from Streptomyces hygroscopicus
Geldanamycin (9CI)

格尔德霉素生物活性

[ 描述 ]:

Geldanamycin是 Hsp90 抑制剂,具有抗许多革兰氏阳性和一些革兰氏阴性细菌的活性。

[ 相关类别 ]:

信号通路 >> 细胞周期/DNA损伤 >> HSP

信号通路 >> 代谢酶/蛋白酶 >> HSP

研究领域 >> 癌症

天然产物 >> 其他

[ 靶点 ]

HSP90:1.2 μM (Kd)

[体外研究]

格尔德霉素显着延迟和降低viperin表达,表明IRF3参与RAW264.7细胞中的viperin诱导[1]。 Geldanamycin(GA),苯醌安沙霉素,在培养的原代神经元中保护免受由氧-葡萄糖剥夺(OGD)/ zVAD处理诱导的神经元损伤。更重要的是,格尔德霉素以时间和浓度依赖性方式降低RIP1蛋白水平。格尔德霉素也降低了Hsp90蛋白水平,导致RIP1蛋白不稳定,导致格尔德霉素处理后RIP1蛋白水平降低但RIP1 mRNA水平降低[2]。格尔德霉素(GA)被确定为Hsp90的第一个天然产物抑制剂,其结合Hsp90的N-末端ATP酶结构域以抑制其伴侣功能,并且通过凋亡机制显着诱导肿瘤细胞死亡[3]。

[参考文献]

[1]. Tang HB, et al. Viperin inhibits rabies virus replication via reduced cholesterol and sphingomyelin and is regulated upstream by TLR4. Sci Rep. 2016 Jul 26;6:30529

[2]. Chen WW, et al. RIP1 mediates the protection of Geldanamycin on neuronal injury induced by oxygen-glucosedeprivation combined with zVAD in primary cortical neurons. J Neurochem. 2012 Jan;120(1):70-7.

[3]. Lin Z, et al. 17-ABAG, a novel Geldanamycin derivative, inhibits LNCaP-cell proliferation through heat shock protein 90 inhibition. Int J Mol Med. 2015 Aug;36(2):424-32.

[4]. Roe SM, et al. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. J Med Chem. 1999 Jan 28;42(2):260-6.

[相关活性小分子]

格尔德霉素物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
783.9±60.0 °C at 760 mmHg

[ 熔点 ]:
255 °C

[ 分子式 ]:
C₂₉H₄₀N₂O₉

[ 分子量 ]:
560.636

[ 闪点 ]:
427.9±32.9 °C

[ 精确质量 ]:
560.273376

[ PSA ]:
163.48000

[ LogP ]:
2.00

[ 外观性状 ]:
黄色至橙色粉末

[ 蒸汽压 ]:
0.0±6.2 mmHg at 25°C

[ 折射率 ]:
1.559

[ 储存条件 ]:
−20°C

[ 水溶解性 ]:
DMSO: soluble

格尔德霉素MSDS

详细MSDS(安全技术说明书)

格尔德霉素毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LX8920000

CHEMICAL NAME :: Geldanamycin

CAS REGISTRY NUMBER :: 30562-34-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C29-H40-N2-O9

MOLECULAR WEIGHT :: 560.71

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 :: 2500 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 :: 1 mg/kg

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

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >50 mg/kg

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

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >4200 ug/kg

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

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 1 mg/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 35,886,1982

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格尔德霉素安全信息

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

[ 危害码 (欧洲) ]:
T: Toxic;

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
26-27-36/37/39

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

[ WGK德国 ]:
2

[ RTECS号 ]:
LX8920000

[ 海关编码 ]:
2933990090

格尔德霉素合成路线

详细合成路线

格尔德霉素上下游产品

格尔德霉素上游产品

格尔德霉素下游产品

格尔德霉素海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 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: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 ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

格尔德霉素文献

The induction of heme oxygenase-1 suppresses heat shock protein 90 and the proliferation of human breast cancer cells through its byproduct carbon monoxide.

Toxicol. Appl. Pharmacol. 274(1) , 55-62, (2014)

Heme oxygenase (HO)-1 is an oxidative stress-response enzyme which catalyzes the degradation of heme into bilirubin, ferric ion, and carbon monoxide (CO). Induction of HO-1 was reported to have antitu...

Bioreduction of aryl azides during mutasynthesis of new ansamitocins.

Org. Lett. 15(17) , 4442-5, (2013)

Supplementing a culture of a mutant strain of Actinosynnema pretiosum that is unable to biosynthesize aminohydroxy benzoic acid (AHBA), with 3-azido-5-hydroxy-benzoic acid and 3-azido-5-amino-benzoic ...

Flotillin depletion affects ErbB protein levels in different human breast cancer cells.

Biochim. Biophys. Acta 1843(9) , 1987-96, (2014)

The ErbB3 receptor is an important regulator of cell growth and carcinogenesis. Among breast cancer patients, up to 50-70% have ErbB3 overexpression and 20-30% show overexpressed or amplified ErbB2. E...

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