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Merck

SML0221

Sigma-Aldrich

荜茇酰胺

≥97% (HPLC)

别名:

5,6-二氢-1-[(2E)-1-氧代-3-(3,4,5-三甲氧基苯基)-2-丙烯-1-基]-2 (1H)-吡啶酮, 5,6-二氢-1-(1-氧代-3-[3,4,5-三甲氧基苯基]- 反式 -2-丙烯基)-2[1 H ]-吡啶酮, 荜茇明碱, 荜茇酰胺

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About This Item

经验公式(希尔记法):
C17H19NO5
CAS号:
分子量:
317.34
MDL號碼:
分類程式碼代碼:
51111800
PubChem物質ID:
NACRES:
NA.77

品質等級

化驗

≥97% (HPLC)

形狀

powder

顏色

white to beige

溶解度

DMSO: ≥5 mg/mL at warmed to 60 °C

儲存溫度

2-8°C

SMILES 字串

COc1cc(\C=C\C(=O)N2CCC=CC2=O)cc(OC)c1OC

InChI

1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+

InChI 密鑰

VABYUUZNAVQNPG-BQYQJAHWSA-N

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一般說明

荜茇酰胺(Piperlongumine)是从胡椒荜茇中提取的生物碱。具有抗动脉粥样硬化、抗焦虑、抗糖尿病、抗抑郁、抗菌、抗血小板、凝集和抗炎活性。荜茇酰胺可抑制肿瘤坏死因子-α和白介素-6的生成。还可抑制核因子-κB (NF-κB)激活,从而防止促炎性反应。荜茇酰胺可抑制斑块形成和血管平滑肌细胞迁移。可用于治疗咳嗽、呼吸道感染和胃痛。

應用

荜茇酰胺已用于研究其对胞质分裂调控蛋白1(PRC1)表达的调节。它还用于体外研究其对人黑色素瘤细胞的抗癌作用。
荜茇酰胺已用于:
  • 作为促氧化药物,用于处理锌指蛋白(ZNF)32表达HepG2细胞
  • 检测其在BV2小胶质细胞中的抗神经炎症作用
  • 检测其对人胃癌细胞株的抑制作用

生化/生理作用

荜茇酰胺选择性地杀死癌细胞而不考虑 p53 状态,而不伤害正常细胞。结合并抑制已知调节氧化应激的蛋白质,特别是谷胱甘肽 S-转移酶 pi 1 (GSTP1)。增加癌细胞中活性氧 (ROS) 级别和凋亡细胞死亡,对快速或缓慢分裂的原代正常细胞几乎没有影响。在多种小鼠肿瘤模型中,荜茇酰胺显示出显著的抗肿瘤作用,并抑制自发形成的恶性乳腺肿瘤及其相关转移瘤的生长。

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

Acute Tox. 4 Oral

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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Piperlongumine induces gastric cancer cell apoptosis and G2/M cell cycle arrest both in vitro and in vivo
Duan C, et al.
Tumour Biology : the Journal of the International Society For Oncodevelopmental Biology and Medicine, 37(8), 10793-10804 (2016)
Alhassan Aodah et al.
PloS one, 11(3), e0151707-e0151707 (2016-03-18)
Piperlongumine is a natural alkaloid extracted from piper plants which has been used traditionally for the treatment of certain diseases. This compound shows interesting in vitro pharmacological activity such as selective anticancer activity and higher cytotoxicity than methotrexate, cyclophosphamide and
Piperlongumine inhibits neuroinflammation via regulating NF-kappaB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells
Kim N, et al.
Journal of Pharmacological Sciences, 137(2), 195-201 (2018)
Monielle Sant'Ana et al.
Pulmonary pharmacology & therapeutics, 61, 101896-101896 (2020-01-29)
Chronic obstructive pulmonary disease (COPD) is related to smoking and anti-inflammatory therapy is indicated. Among the mediators with anti-inflammatory properties, we highlight piperlongumine (PL), an alkaloid/amide of Piper longum. Here we evaluated the PL administration on an experimental model of
Ding-Fang Zhang et al.
BMC complementary medicine and therapies, 21(1), 195-195 (2021-07-08)
Metastatic castration-resistant prostate cancer (CRPC) is the leading cause of death among men diagnosed with prostate cancer. Piperlongumine (PL) is a novel potential anticancer agent that has been demonstrated to exhibit anticancer efficacy against prostate cancer cells. However, the effects

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