Protopine

• CAT Number: I001178
• CAS Number: 130-86-9
• Molecular Formula: C20H19NO5
• Molecular Weight: 353.37
• Purity: ≥95%
• Synonyms: 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
• InChI: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
• InChIKey: GPTFURBXHJWNHR-UHFFFAOYSA-N
• SMILES: CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3

Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].
Protopine (10-40 μM, 24 h-96 h) inhibits cell viability, migration, invasion and EMT process of liver carcinoma cells (HepG2, Huh7)[2].
Protopine (10-40 μM, 24 h) induces apoptosis by increasing the expression of caspase-3 and caspase-9 in HepG2 and Huh7 cells, and inhibits the PI3K/Akt signaling pathway[2].
Protopine (10-40 μM, 6 h) induces generation of ROS in HepG2 and Huh7 cells[2].
Protopine (0-10 μg/mL) inhibits the uptake of serotonin transporter (SERT) in S6 cells and noradrenaline (NE) uptake in N1 cells[3].
Protopine (0.1 and 1 mg/kg, i.p.) alleviates Scopolamine (HY-N0296) (1 mg/kg)-induced memory impairment in mice[1].
Protopine (5-20 mg/kg, i.v.) 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.) shows antidepressant-like effect in mice HTR and TST tests[3].
Protopine (1-4 mg/kg, i.p., once daily for 3 days) shows protective effect on the focal cerebral ischaemic induced injury in rats[4].

Reference

[1]. Kim SR, et, al. Protopine from Corydalis ternata has anticholinesterase and antiamnesic activities. Planta Med. 1999 Apr;65(3):218-21.
 [Content Brief]

[2]. Nie C, et, al. 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.
 [Content Brief]

[3]. Xu LF, et al. Protopine inhibits serotonin transporter and noradrenaline transporter and has the antidepressant-like effect in mice models. Neuropharmacology. 2006 Jun;50(8):934-40.
 [Content Brief]

[4]. Xiao X, et al. Protective effect of protopine on the focal cerebral ischaemic injury in rats. Basic Clin Pharmacol Toxicol. 2007 Aug;101(2):85-9.
 [Content Brief]