Protopine (hydrochloride)
(Synonyms: 盐酸前鸦片碱) 目录号 : GC44732
An alkaloid with diverse biological activities
Cas No.:6164-47-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Protopine is an alkaloid found in Berberidaceae, Ranunculaceae, Rutaceae, Fumariaceae, and Papaveraceae with diverse biological activities. It inhibits platelet aggregation induced by ADP, arachidonic acid , platelet-activating factor (PAF), and collagen in rabbit platelet-rich plasma at a concentration of 100 μM. Protopine inhibits contraction of isolated rat thoracic aorta induced by norepinephrine and is a non-selective inhibitor of ICa, IK, IK1, and INa in guinea pig ventricular myocytes. Protopine inhibits the growth of H. pylori with an MIC50 value of 100 μg/ml. It reduces growth of PC3 and DU145 prostate cancer cells in a dose-dependent manner via induction of mitotic cell cycle arrest. Protopine (0.005 mg/kg) increases latency to first seizure in a mouse model induced by pentylenetetrazole .
| Cas No. | 6164-47-2 | SDF | |
| 别名 | 盐酸前鸦片碱 | ||
| Canonical SMILES | O=C1CC2=C(C(OCO3)=C3C=C2)CN(C)CCC4=CC5=C(OCO5)C=C41.Cl | ||
| 分子式 | C20H19NO5•HCl | 分子量 | 389.8 |
| 溶解度 | DMF: 0.1 mg/ml,DMSO: 0.1 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.5654 mL | 12.8271 mL | 25.6542 mL |
| 5 mM | 0.5131 mL | 2.5654 mL | 5.1308 mL |
| 10 mM | 0.2565 mL | 1.2827 mL | 2.5654 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Protopine hydrochloride
Acta Crystallogr C 2001 May;57(Pt 5):651-2.PMID:11353282DOI:10.1107/s0108270101003249.
Protopine hydrochloride (5,6,14,14a-tetrahydro-14a-hydroxy-7-methyl-8H-bis[1,3]benzodioxolo[5,6-a:4,5-g]quinolizinium chloride, C20H20NO5(+)-Cl(-)) is the salt of the isoquinoline alkaloid Protopine. It is formed by the action of dilute hydrochloric acid on the Protopine free base. The N-methyl and hydroxyl groups are in a trans configuration in the quinolizine ring and the central quinolizine N-C bond is unusually long [1.579 (2) A]. The crystal is a racemate.
Protopine Protects Mice against LPS-Induced Acute Kidney Injury by Inhibiting Apoptosis and Inflammation via the TLR4 Signaling Pathway
Molecules 2019 Dec 19;25(1):15.PMID:31861525DOI:10.3390/molecules25010015.
Corydalis humosa Migo is a traditional Chinese medicine that clears away damp heat, relieves sore. Protopine (PRO) is an alkaloid component isolated from C. humosa Migo. However, the role of Protopine in acute kidney injury (AKI) has not yet been reported. This study aims to investigate the effect and mechanism of Protopine isolated from C. humosa Migo on lipopolysaccharide (LPS)-induced AKI in mice. Inflammation accumulation was assessed by small animal living imaging. The blood urea nitrogen (BUN), and serum creatinine (Scr) were measured to assess the effects of Protopine on renal function in LPS-induced AKI. The levels of tumor necrosis factor (TNF), interleukin-2 (IL-2), interferon-γ (IFN-γ), and (interleukin-10) IL-10 in serum were detected by cytometric bead array. Flow cytometry was used to detect the levels of reactive oxygen species (ROS) in primary kidney cells. The proportions of granulocytes, neutrophils, and macrophages in peripheral blood were examined to evaluate the effect of Protopine on immune cells in mice with AKI. Toll-like receptor (TLR4) and apoptotic signaling pathway were detected by Western blot analysis. The results showed that Protopine markedly improved the renal function, relieve inflammation, reversed inflammatory cytokines, transformed apoptosis markers, and regulated the TLR4 signaling pathway in mice with AKI induced by LPS. The Protopine isolated from C. humosa Migo protected mice against LPS-induced AKI by inhibiting apoptosis and inflammation via the TLR4 signaling pathway, thus providing a molecular basis for a novel medical treatment of AKI.
Protopine promotes the proteasomal degradation of pathological tau in Alzheimer's disease models via HDAC6 inhibition
Phytomedicine 2022 Feb;96:153887.PMID:34936968DOI:10.1016/j.phymed.2021.153887.
Background: Collective evidences have indicated that intracellular accumulation of hyperphosphorylated tau forms neurofibrillary tangles in the brain, which impairs memory, cognition and affects social activities in Alzheimer's disease (AD). Purpose: To investigate the tau-reducing, and memory-enhancing properties of Protopine (PRO), a natural alkaloid isolated from Chinese herbal medicine Corydalis yanhusuo (Yanhusuo in Chinese). Study design: By using Histone deacetylase 6 (HDAC6) profiling and immunoprecipitation assays, we assessed that PRO mediated the heat shock protein 90 (HSP90) chaperonic activities for the degradation of pathological tau in AD cell culture models. To study the efficacy of PRO in vivo, we employed 3xTg-AD and P301S tau mice models. Methods: Liquid chromatography/quadrupole time-of-flight mass spectrometry was used to analyze the pharmacokinetic profile of PRO. Seven-month-old 3xTg-AD mice and 1.5-month-old P301S mice were administered PRO (1 and 2.5 mg/kg) orally every day. Morris water maze, contextual fear conditioning and rotarod assays were applied for studying memory functions. Sarkosyl differential centrifugation was used to analyze soluble and insoluble tau. Immunohistochemical analysis were performed to determine tau deposits in AD mice's brain sections. Molecular docking, binding affinity studies and primary cell culture studies were performed to demonstrate the mechanism of action of PRO in silico and in vitro. Results: Our pharmacokinetic profiling demonstrated that PRO significantly entered the brain at a concentration of 289.47 ng/g, and specifically attenuated tau pathology, improved learning and memory functions in both 3xTg-AD and P301S mice. Docking, binding affinity studies, and fluorometric assays demonstrated that PRO directly bound to the catalytic domain 1 (CD1) of HDAC6 and down-regulated its activity. In primary cortical neurons, PRO enhanced acetylation of α-tubulin, indicating HDAC6 inhibition. Meanwhile, PRO promoted the ubiquitination of tau and recruited heat shock protein 70 (HSP70) and heat shock cognate complex 71 (HSC70) for the degradation of pathological tau via the ubiquitin-proteasomal system (UPS). Conclusion: We identified PRO as a natural HDAC6 inhibitor that attenuated tau pathology and improved memory dysfunctions in AD mice. The findings from this study provides a strong justification for future clinical development of plant-derived Protopine as a novel agent for the treatment of tau-related neurodegenerative diseases.
Identification and Quantification, Metabolism and Pharmacokinetics, Pharmacological Activities, and Botanical Preparations of Protopine: A Review
Molecules 2021 Dec 30;27(1):215.PMID:35011447DOI:10.3390/molecules27010215.
Through pharmacological activity research, an increasing number of natural products and their derivatives are being recognized for their therapeutic value. In recent years, studies have been conducted on Corydalis yanhusuo W.T. Wang, a valuable medicinal herb listed in the Chinese Pharmacopoeia. Protopine, one of its components, has also become a research hotspot. To illustrate the identification, metabolism, and broad pharmacological activity of Protopine and the botanical preparations containing it for further scientific studies and clinical applications, an in-depth and detailed review of Protopine is required. We collected data on the identification and quantification, metabolism and pharmacokinetics, pharmacological activities, and botanical preparations of Protopine from 1986 to 2021 from the PubMed database using "Protopine" as a keyword. It has been shown that Protopine as an active ingredient of many botanical preparations can be rapidly screened and quantified by a large number of methods (such as the LC-ESI-MS/MS and the TLC/GC-MS), and the possible metabolic pathways of Protopine in vivo have been proposed. In addition, Protopine possesses a wide range of pharmacological activities such as anti-inflammatory, anti-platelet aggregation, anti-cancer, analgesic, vasodilatory, anticholinesterase, anti-addictive, anticonvulsant, antipathogenic, antioxidant, hepatoprotective, neuroprotective, and cytotoxic and anti-proliferative activities. In this paper, the identification and quantification, metabolism and pharmacokinetics, pharmacological activities, and botanical preparations of Protopine are reviewed in detail to lay a foundation for further scientific research and clinical applications of Protopine.
Protopine triggers apoptosis via the intrinsic pathway and regulation of ROS/PI3K/Akt signalling pathway in liver carcinoma
Cancer Cell Int 2021 Jul 27;21(1):396.PMID:34315493DOI:10.1186/s12935-021-02105-5.
Background: Protopine is an isoquinoline alkaloid that possesses various biological activities including the anti-tumour activity. However, the effects of Protopine on liver carcinoma cells are still elusive. The aim of this study is to examine the effects of Protopine on liver carcinoma cells both in vitro and in vivo. Methods: MTT assay was performed to measure the cell viability. Wound healing and transwell assays were conducted to assess the motility of cells. Cellular apoptosis and ROS levels were measured by the flow cytometry. Western blotting assay was used to measure the change of proteins. The cytotoxicity of Protopine was also evaluated in xenograft mice. Results: Protopine inhibited viabilities and triggered apoptosis via the intrinsic pathway in a caspase-dependent manner in liver carcinoma cells. Furthermore, Protopine also induced accumulation of intracellular ROS which further led to the inhibition of PI3K/Akt signalling pathway. Finally, in vivo study showed that Protopine also repressed tumour growth in xenograft mice without noticeable toxicity. Conclusions: Protopine might be used as a potential therapeutic agent for the treatment of liver carcinoma.