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  • China
  • Product Name: Protopine
  • Price: ¥Inquiry/5mg
  • Purity: 98.0%
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130-86-9

130-86-9 structure
130-86-9 structure
  • Name: Protopine
  • Chemical Name: protopine
  • CAS Number: 130-86-9
  • Molecular Formula: C20H19NO5
  • Molecular Weight: 353.369
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-07-09 09:32:17
  • Modify Date: 2024-01-02 09:33:51
  • Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: 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 [2]. 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 [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].

Name protopine
Synonyms 7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one
Protopine
7-Methyl-6,8,9,16-tetrahydro[1,3]dioxolo[5,6]benzo[1,2-c][1,3]dioxolo[4,5]benzo[1,2-g]azecin-15(7H)-on
Biflorine
Protopin
Bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one, 6,8,9,16-tetrahydro-7-methyl-
EINECS 204-999-6
4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one
BIFLORIN
Hypercorine
4,6,7,14-Tetrahydro-5-Methyl
Tangeratin
Corydinine
Corydalis C
Description Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: 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 [2]. 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 [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].
Related Catalog
References

[1]. Bae DS, et al. Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages. BMB Rep. 2012 Feb;45(2):108-13.

[2]. Chen CH, et al. Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Cancer Lett. 2012 Feb 1;315(1):1-11.

[3]. Vrba J, et al. Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett. 2011 Jun 10;203(2):135-41.

[4]. He K, et al. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. Afr J Tradit Complement Altern Med. 2014 Jan 28;11(2):415-24.

Density 1.3±0.1 g/cm3
Boiling Point 547.5±49.0 °C at 760 mmHg
Melting Point 211ºC
Molecular Formula C20H19NO5
Molecular Weight 353.369
Flash Point 284.9±29.8 °C
Exact Mass 353.126312
PSA 57.23000
LogP 3.76
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.613
Storage condition Refrigerator

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VS2800000
CAS REGISTRY NUMBER :
130-86-9
LAST UPDATED :
199803
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C20-H19-N-O5
MOLECULAR WEIGHT :
353.40
WISWESSER LINE NOTATION :
T I5 F6 C-10-65 DV JO LO PN VO A&O KH&&T&&J P1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,24,1953
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
482 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 16(6),7,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
31 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,640,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
237 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 28,767,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
116 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 28,767,1973
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310 + P330
Safety Phrases 24/25
RIDADR UN 1544
RTECS VS2800000
Packaging Group III
Hazard Class 6.1(b)