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PROTOPINE HYDROCHLORIDE

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PROTOPINE HYDROCHLORIDE Basic information

Product Name:
PROTOPINE HYDROCHLORIDE
Synonyms:
  • 13a-secoberbin-13a-one,7-methyl-2,3:9,10-bis(methylenedioxy)-hydrochloride
  • PROTOPINE HCL
  • PROTOPINE HYDROCHLORIDE
  • MACLEYINE
  • FUMARINE
  • FUMARINE HYDROCHLORIDE
  • 7,13A-Secoberbin-13A-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride
  • Argemonine (protopine
CAS:
6164-47-2
MF:
C20H20ClNO5
MW:
389.83
EINECS:
228-196-5
Product Categories:
  • Nutrition Research
  • Alkaloids
  • AlkaloidVoltage-gated Ion Channels
  • Biochemicals Found in Plants
  • Calcium Channel Modulators
  • Inhibitors and Activators
Mol File:
6164-47-2.mol
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PROTOPINE HYDROCHLORIDE Chemical Properties

storage temp. 
2-8°C
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form 
solid
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
36/37/39-45
RIDADR 
1544
WGK Germany 
3
RTECS 
UL2000000
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
6164-47-2(Hazardous Substances Data)
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PROTOPINE HYDROCHLORIDE Usage And Synthesis

Description

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 (Item Nos. 90010 | 90010.1 | 10006607), 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 .

Uses

Protopine hydrochloride may be used in the calibration curve preparation for the quantification of alkaloids from Fumaria capreolata using liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-MS) and tandem mass spectrometry(MS/MS). It may also be used as an alkaloid in cytotoxicity and permeability studies carcinogenic cell lines.

General Description

Protopine is a celandine alkaloid and a bioactive compound associated with the plant families including fumariaceae, berberidaceae?and papaveraceae. It is metabolized by demethylenation in the presence of the cytochrome enzymes cytochrome P450 family 2 subfamily d polypeptide 1 (CYP2D1) and cytochrome P450 family 2 subfamily c polypeptide 11 (CYP2C11).

Biochem/physiol Actions

Protopine possesses anti-parasitic, antimicrobial and anti-inflammatory property. It mediates mitotic arrest by favoring tubulin polymerization. Protopine elicits anti-invasive effects in breast cancer tumor progression.. It also provides protection against oxidative stress-induced cell death.

in vivo

Protopine (0.1 and 1 mg/kg, i.p.) hydrochloride alleviates Scopolamine (HY-N0296) (1 mg/kg)-induced memory impairment in mice[1].
Protopine (5-20 mg/kg, i.v.) hydrochloride inhibits tumor growth and inhibits PI3K/Akt, and induces cleavage of caspase-3 in xenograft BALB/c mice (s.c. with HepG2 or Huh-7 cells)[2].
Protopine (5-20 mg/kg, i.p.) hydrochloride shows antidepressant-like effect in mice HTR and TST tests[3].
Protopine (1-4 mg/kg, i.p., once daily for 3 days) hydrochloride shows protective effect on the focal cerebral ischaemic induced injury in rats[4].

Animal Model:5-hydroxy-DL-tryptophan (5-HTP)-induced mice model[3]
Dosage:5, 10, 20 mg/kg
Administration:i.p.
Result:Increased the number of 5-HTP-induced head twitch response (HTR).
Decreased the immobility time tested in the Tail suspension test (TST).

References

[1] LEVENT üSTüNES. In Vitro Study of the Anticholinergic and Antihistaminic Activities of Protopine and Some Derivatives[J]. Journal of Natural Products , 1988, 51 5: 1021-1022. DOI: 10.1021/np50059a043
[2] FENG-NIEN KO . Antiplatelet effects of protopine isolated from Corydalis tubers[J]. Thrombosis research, 1989, 56 2: Pages 289-298. DOI: 10.1016/0049-3848(89)90170-9
[3] FENG-NIEN KO . Ca2+-Channel Blockade in Rat Thoracic Aorta by Protopine Isolated from Corydalis Tubers[J]. Japanese journal of pharmacology, 1992, 58 1: Pages 1-9. DOI: 10.1016/s0021-5198(19)39771-9
[4] LONG-SHENG SONG. Electrophysiological effects of protopine in cardiac myocytes: inhibition of multiple cation channel currents[J]. British Journal of Pharmacology, 2009, 129 5: 893-900. DOI: 10.1038/sj.bjp.0703132
[5] GAIL B MAHADY. In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis.[J]. Phytotherapy Research, 2003, 17 3: 217-221. DOI: 10.1002/ptr.1108
[6] CHUN-HAN CHEN . Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines[J]. Cancer letters, 2012, 315 1: Pages 1-11. DOI: 10.1016/j.canlet.2011.09.042
[7] Y. PROKOPENKO. In Vivo Anticonvulsant Activity of Extracts and Protopine from the Fumaria schleicheri Herb[J]. Scientia Pharmaceutica, 2015, 13 1: 547-554. DOI: 10.3390/scipharm84030547

PROTOPINE HYDROCHLORIDESupplier

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