Sinomenine hydrochloride

Sinomenine hydrochloride (Cucoline hydrochloride), an alkaloid extracted from Sinomenium acutum, is a blocker of the NF-κB activation. Sinomenine also is an activator of μ-opioid receptor.

Product information

CAS Number: 6080-33-7

Molecular Weight: 365.85

Formula: C19H24ClNO4

Synonym:

Cucoline hydrochloride

Chemical Name: (1R, 9S, 10S)-3-hydroxy-4, 12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0, .0, ]heptadeca-2, 4, 6, 11-tetraen-13-one hydrochloride

Smiles: Cl.COC1=C[C@@H]2[C@@H]3CC4=CC=C(OC)C(O)=C4[C@@]2(CC1=O)CCN3C

InChiKey: YMEVIMJAUHZFMW-VUIDNZEBSA-N

InChi: InChI=1S/C19H23NO4.ClH/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19;/h4-5,9,12-13,22H,6-8,10H2,1-3H3;1H/t12-,13+,19-;/m1./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 100 mg/mL (273.34 mM; Need ultrasonic and warming) H2O : 16.67 mg/mL (45.57 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Cell viability is gradually decreased with increasing Sinomenine hydrochloride concentration. The migration ability of MDA-MB-231 cells is significantly weakened by 0.25, 0.5, and 1 mM of Sinomenine hydrochloride treatment. The wound-healing assay reveals that 0.25 and 0.5 mM Sinomenine hydrochloride significantly suppress the healing of the wound. When the MDA-MB-231 cells are treated with 0.5 mM Sinomenine hydrochloride, the healing progress is about 50%, but in the group treated with 0.25 mM Sinomenine hydrochloride and the untreated control, the healing is about 80% and nearly 95%, respectively. The IB assay following inhibitor of NF-κB (IκB) antibody IP shows that the binding of NF-κB to IκB is inhibited by Sinomenine hydrochloride treatment in a dose-dependent manne.

In Vivo:

Sinomenine hydrochloride (i.p.) produces antinociception in the hot plate and tail flick tests in male rats at 40 mg/kg, but not at lower doses (10 or 20 mg/kg). At 10 to 40 mg/kg Sinomenine hydrochloride does not produce any observable side effect such as sedation, allergy or motor impairments. At 80 mg/kg, Sinomenine hydrochloride is mildly sedative in rats. Sinomenine hydrochloride at 80 mg/kg i.p. does not produce any observable side effects in mice. I.p or p.o. Sinomenine hydrochloride at 40 or 80 mg/kg dose-dependently reduces mechanical hypersensitivity in nerve injured mice. I.p. Sinomenine hydrochloride at 40 mg/kg, but not lower doses or vehicle, significantly decreases mechanical and cold allodynia for up to 240 min without producing motor deficits or sedation. At doses of 10 to 40 mg/kg, Sinomenine hydrochloride dose-dependently increases the paw withdrawal threshold. In non-chronic constriction injury (CCI) healthy rats, Sinomenine hydrochloride at the dose range of 10 to 40 mg/kg does not change the immobility behavior in the forced swimming test.

References:

1. Song L, et al. Sinomenine inhibits breast cancer cell invasion and migration by suppressing NF-κB activation mediated by IL-4/miR-324-5p/CUEDC2 axis. Biochem Biophys Res Commun. 2015 Aug 28;464(3):705-10.
2. Gao T, et al. Analgesic effect of sinomenine in rodents after inflammation and nerve injury. Eur J Pharmacol. 2013 Dec 5;721(1-3):5-11.
3. Wang MH, et al. Activation of opioid mu-receptor by sinomenine in cell and mice.Neurosci Lett. 2008 Oct 10;443(3):209-12.
4. Zhu Q, et al. Antinociceptive effects of sinomenine in a rat model of neuropathic pain. Sci Rep. 2014 Dec 1;4:7270.

Products are for research use only. Not for human use.