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53109-32-3

中文名稱 環(huán)(組氨酰-脯氨酰)
英文名稱 CYCLO(-HIS-PRO)
CAS 53109-32-3
分子式 C11H14N4O2
分子量 234.25
MOL 文件 53109-32-3.mol
更新日期 2024/12/03 15:40:34
53109-32-3 結(jié)構(gòu)式 53109-32-3 結(jié)構(gòu)式

基本信息

中文別名
環(huán)(組氨酰-脯氨酰)
(3S,8AS)-六氫-3-(1H-咪唑-4-基甲基)吡咯并[1,2-A]吡嗪-1,4-二酮
英文別名
CYCLO(-HIS-PRO)
HIS-PRO, CYCLIC
Cyclo-Pro-His-HO
CYCLO(HIS-PRO), >99%
Cyclo(histidyl-proline)
Protirelin EP Impurity E
Cyclo(L-histidyl-L-proline)
histidylproline dioxopiperazine
Histidylproline diketopiperazine
CYCLO(HISTIDYL-PROLINE)
HISTIDYLPROLINE DIKETOPIPERAZINE

物理化學(xué)性質(zhì)

熔點162-164 °C
沸點659.3±48.0 °C(Predicted)
密度1.41±0.1 g/cm3(Predicted)
儲存條件2-8°C
溶解度DMF: 1 mg/ml; DMSO: 1 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 1 mg/ml
酸度系數(shù)(pKa)12.73±0.40(Predicted)
形態(tài)A neat oil
顏色Light yellow to yellow

安全數(shù)據(jù)

危險性符號(GHS)GHS hazard pictograms
GHS07
警示詞警告
危險性描述H302-H315-H319-H335
WGK Germany3

常見問題列表

生物活性
Cyclo(his-pro) (Cyclo(histidyl-proline)) 是一種具有口服活性的,結(jié)構(gòu)上與促甲狀腺激素釋放激素相關(guān)的環(huán)狀二肽。Cyclo(his-pro) 可以抑制 NF-κB 核積累。Cyclo(his-pro) 可以穿越腦血屏障并影響多種炎癥和應(yīng)激反應(yīng)。
靶點

NF-κB

Human Endogenous Metabolite

體外研究

cyclo(his-pro) (Cyclo(histidyl-proline); 50 μM; 1-48 hours) increases the nuclear level of Nrf2 and inhibits NF-κB nuclear translocation. Cyclo(His-Pro) alone has no effect on nuclear translocation of these transcription factors.
cyclo(his-pro) (50 μM; prior to PQ exposure for 48 hours) abolishes protein nitration that followed paraquat (PQ) exposure and lessenes its functional consequences, as shown by decrease in cell apoptosis, detected by caspase 3 activity and by cytochrome c release.
Cyclo(his-pro) inhibits NF-κB nuclear accumulation induced by paraquat in rat pheochromocytoma PC12 cells via the Nrf2/heme oxygenase-1 pathway.

Western Blot Analysis

Cell Line: PC12 cells
Concentration: 50 μM
Incubation Time: 1, 2, 4, 8, 24, 48 hours
Result: Increased the nuclear level of Nrf2 and inhibited NF-κB nuclear translocation.
體內(nèi)研究

Cyclo(his-pro) (Cyclo(histidyl-proline); 1.8 mg/ear; topical application on the right ear; 30 min prior to TPA) reduces TPA-induced ear oedema confirming that it can exert anti-inflammatory effect.
Cyclo(his-pro) exerts in vivo anti-inflammatory effects in the central nervous system by down-regulating hepatic and cerebral TNFα expression thereby counteracting LPS-induced gliosis. Moreover, by up-regulating Bip, Cyclo(his-pro) increases the ER stress sensitivity andtriggers the unfolded protein response to alleviate the ER stress.

Animal Model: Sixty two/three month-old male C57BL/6 mice (25-30 g)
Dosage: 1.8 mg/ear
Administration: Topical application on the right ear; 30 min prior to TPA
Result: Reduced TPA-induced ear oedema.
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