Protopine | CAS:130-86-9 | Manufacturer ChemFaces

Protopine

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Description:

Protopine acts as a potent inhibitor of thromboxane synthesis and PAF with hepatoprotective, antidepressant, antioxidant, antispasmodic and relaxant properties. Protopine is also a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Protopine blocks phosphorylation of mitogen-activated protein kinases (MAP kinases) and also blocks activation of a nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB).

Targets:

In vitro:

Afr. J. Tradit. Complement. Altern. Med., 2014 Jan 28;11(2):415-24.

Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors.[Pubmed: 25435628]

A Chinese herb Corydalis yanhusuo W.T. Wang that showed anticancer and anti-angiogenesis effects in our previous studies was presented for further studies. In the present study, we studied the anticancer proliferation and adhesion effects of five alkaloids which were isolated from Corydalis yanhusuo.
METHODS AND RESULTS:
MTT dose response curves, cell migration assay, cell invasion assay, as well as three types of cell adhesive assay were performed on MDA-MB-231 human breast cancer cells. The mechanism of the compounds on inhibiting heterotypic cell adhesion were further explored by determining the expression of epidermal growth factor receptor (EGFR), Intercellular adhesion molecule 1 (ICAM-1), αv-integrin, β1-integrin and β5-integrin by western blotting assay. In five tested alkaloids, only Protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells, which contributed to the anti-metastasis effect of Corydalis yanhusuo. The results showed that after treatment with Protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced.
CONCLUSIONS:
The present results suggest that Protopine seems to inhibit the heterotypic cell adhesion between MDA-MB-231 cells, and human umbilical vein endothelial cells by changing the expression of adhesive factors.

In vivo:

Pharmacol Res. 1997 Jul;36(1):1-7.

Anti-thrombotic and anti-inflammatory activities of protopine.[Pubmed: 9368908 ]

METHODS AND RESULTS:
The effects of Protopine on human platelet aggregation and arachidonic acid (AA) metabolism via cyclooxygenase (COX) and lipoxygenase (LOP) enzymes were examined. Platelet aggregation induced by various platelet agonists (AA, ADP, collagen and PAF) was strongly inhibited by Protopine in a concentration-related manner. The IC50 values (microM) of Protopine (mean +/- SEM) against: AA; 12 +/- 2: ADP; 9 +/- 2: collagen; 16 +/- 2 and PAF; 11 +/- 1, were much less than those observed for aspirin. In addition, Protopine selectively inhibited the synthesis of thromboxane A2 (TXA2) via COX pathway and had no effect on the LOP pathway in platelets. In vivo, pretreatment with Protopine (50-100 mg kg-1) protected rabbits from the lethal effects of AA (2 mg kg-1) or PAF (11 micrograms kg-1) in dose-dependent fashion. Protopine (50-100 mg kg-1) also inhibited carrageenan-induced rat paw oedema with a potency of three-fold as compared to aspirin.
CONCLUSIONS:
These results are suggestive that Protopine acts as a potent inhibitor of thromboxane synthesis and PAF with anti-inflammatory properties.

Phytomedicine. 2008 Jun;15(6-7):470-7.

Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine.[Pubmed: 18164606 ]

METHODS AND RESULTS:
The present investigation demonstrates the hepatoprotective potential of 50% ethanolic water extract of whole plant of Fumaria indica and its three fractions viz., hexane, chloroform and butanol against d-galactosamine induced hepatotoxicity in rats. The hepatoprotection was assessed in terms reduction in histological damage, changes in serum enzymes (SGOT, SGPT, ALP) and metabolites bilirubin, reduced glutathione (GSH) and lipid peroxidation (MDA content). Among fractions more than 90% protection was found with butanol fraction in which alkaloid Protopine was quantified as highest i.e. about 0.2mg/g by HPTLC. The isolated Protopine in doses of 10-20mg p.o. also proved equally effective hepatoprotectants as standard drug silymarine (single dose 25mg p.o.).
CONCLUSIONS:
In general all treatments excluding hexane fraction proved hepatoprotective at par with silymarine (p

Planta Med. 1998 Dec;64(8):758-60.

Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum.[Pubmed: 9933996 ]

METHODS AND RESULTS:
Two ethanolic dry extracts from the herb Chelidonium majus L. with a defined content of the main alkaloids (chelidonine, Protopine, and coptisisine) and the alkaloids themselves were studied in three different antispasmodic test models on isolated ileum of guinea-pigs. In the BaCl2-stimulated ileum, chelidonine and Protopine exhibited the known papaverine-like musculotropic action, whereas coptisine (up to 3.0 x 10(-5) g/ml) was ineffective in this model. Both extracts were active with 53.5% and 49.0% relaxation at 5 x 10(-4) g/ml. The carbachol and the electric field stimulated contractions were antagonized by all three alkaloids. Coptisine showed competitive antagonist behaviour with a pA2 value of 5.95. Chelidonine and Protopine exhibited a certain degree of non-competitive antagonism.
CONCLUSIONS:
In the electric field the antagonist activities decreased in the order Protopine > coptisine > chelidonine. The concentrations of the chelidonium herb extracts for 50% inhibition of the carbachol and electrical field induced spasms were in the range of 2.5 to 5 x 10(-4) g/ml.

Protopine Description

Source:	The tubers of Corydalis yanhusuo W.T.Wang.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

BMB Rep. 2012 Feb;45(2):108-13.

Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages.[Pubmed: 22360889]

Protopine is an isoquinoline alkaloid contained in plants in northeast Asia.
METHODS AND RESULTS:
In this study, we investigated whether Protopine derived from Hypecoum erectum L could suppress lipopolysaccharide (LPS)-induced inflammatory responses in murine macrophages (Raw 264.7 cells). Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with Protopine reduced the production of pro-inflammatory cytokines.
CONCLUSIONS:
These inhibitory effects were caused by blocking phosphorylation of mitogen-activated protein kinases (MAP kinases) and also blocking activation of a nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB).

Cancer Lett. 2012 Feb 1;315(1):1-11.

Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines.[Pubmed: 22033245 ]

METHODS AND RESULTS:
In this study, we investigated the anticancer effect of Protopine on human hormone-refractory prostate cancer (HRPC) cells. Protopine exhibited an anti-proliferative effect by induction of tubulin polymerization and mitotic arrest, which ultimately led to apoptotic cell death. The data suggest that Protopine increased the activity of cyclin-dependent kinase 1 (Cdk1)/cyclin B1 complex and that contributed to cell apoptosis by modulating mitochondria-mediated signaling pathways, such as Bcl-2 phosphorylation and Mcl-1 down-regulation.
CONCLUSIONS:
In conclusion, the data suggest that Protopine is a novel microtubule stabilizer with anticancer activity in HRPC cells through apoptotic pathway by modulating Cdk1 activity and Bcl-2 family of proteins.

Cell Research:

Eur J Pharmacol. 2008 Sep 4;591(1-3):21-7.

Protective effects of protopine on hydrogen peroxide-induced oxidative injury of PC12 cells via Ca(2+) antagonism and antioxidant mechanisms.[Pubmed: 18602385 ]

Calcium and lipid peroxidation play important roles in oxidative stress-induced cellular injury and apoptosis, which ultimately cause cell death.
METHODS AND RESULTS:
In this study we examined whether Protopine had a neuroprotection against H(2)O(2)-induced injury in PC12 cells. Pretreatment of PC12 cells with Protopine improved the cell viability, enhanced activities of superoxide dismutase, glutathione peroxidase and catalase, and decreased malondialdehyde level in the H(2)O(2) injured cells. Protopine also reversed the increased intracellular Ca(2+) concentration and the reduced mitochondrial membrane potential caused by H(2)O(2) in the cells. Furthermore, Protopine was able to inhibit caspase-3 expression and cell apoptosis induced by H(2)O(2).
CONCLUSIONS:
In summary, this study demonstrates that Protopine is able to relieve H(2)O(2)-induced oxidative stress and apoptosis in PC12 cells, at least in part, by Ca(2+) antagonism and antioxidant mechanisms.

Animal Research:

Neuropharmacology. 2006 Jun;50(8):934-40.

Protopine inhibits serotonin transporter and noradrenaline transporter and has the antidepressant-like effect in mice models.[Pubmed: 16530230]

The Protopine isolated from a Chinese herb Dactylicapnos scandens Hutch was identified as an inhibitor of both serotonin transporter and noradrenaline transporter in vitro assays.
METHODS AND RESULTS:
5-hydroxy-DL-tryptophan(5-HTP)-induced head twitch response (HTR) and tail suspension test were adopted to study whether Protopine has anti-depression effect in mice using reference antidepressant fluoxetine and desipramine as positive controls. In HTR test, Protopine at doses of 5, 10, 20 mg/kg dose dependently increase the number of 5-HTP-induced HTR. Protopine at doses of 3.75 mg/kg, 7.5 mg/kg and 30 mg/kg also produces a dose-dependent reduction in immobility in the tail suspension test.
CONCLUSIONS:
The present results open up new possibilities for the use of Protopine in the treatment of mood disorders, such as mild and moderate states of depression.

CAS No.	130-86-9	Price	$50 / 20mg
Catalog No.	CFN99399	Purity	>=98%
Molecular Weight	353.4	Type of Compound	Alkaloids
Formula	C₂₀H₁₉NO₅	Physical Description	Powder
Download	COA MSDS SDF Manual	Similar structural	Comparison (Web) (SDF)

Product Name	Protopine
CAS No.:	130-86-9
Catalog No.:	CFN99399
Molecular Formula:	C₂₀H₁₉NO₅
Molecular Weight:	353.4 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Targets:	COX \| EGFR \| Integrin \| Calcium Channel \| Caspase \| NF-kB \| 5-HT Receptor \| CDK \| Bcl-2/Bax \| PGE \| NO
Source:	The tubers of Corydalis yanhusuo W.T.Wang.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price:	$50 / 20mg
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.8297 mL	14.1483 mL	28.2965 mL	56.5931 mL	70.7414 mL
5 mM	0.5659 mL	2.8297 mL	5.6593 mL	11.3186 mL	14.1483 mL
10 mM	0.283 mL	1.4148 mL	2.8297 mL	5.6593 mL	7.0741 mL
50 mM	0.0566 mL	0.283 mL	0.5659 mL	1.1319 mL	1.4148 mL
100 mM	0.0283 mL	0.1415 mL	0.283 mL	0.5659 mL	0.7074 mL

CFN98051	Mangochinine	209115-67-3	328.4	C₁₉H₂₂NO₄
CFN98254	Allocryptopine	24240-04-8	369.4	C₂₁H₂₃NO₅
CFN99143	Phellodendrine	6873-13-8	342.4	C₂₀H₂₄NO₄
CFN99144	Phellodendrine chloride	104112-82-5	377.85	C₂₀H₂₄NO₄.Cl
CFN99388	Hydroprotopine	128397-41-1	354.4	C₂₀H₂₀NO₅
CFN99399	Protopine	130-86-9	353.4	C₂₀H₁₉NO₅
CFN89127	Coulteropine	6014-62-6	383.4	C₂₁H₂₁NO₆
CFN89163	1-Methoxyallocryptopine	56743-52-3	399.44	C₂₂H₂₅NO₆