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Lycorine hydrochloride

Product NameLycorine hydrochloride
CAS2188-68-3
MFC16H17NO4
MW287.31
EINECS
MOL File2188-68-3.mol

Chemical Properties

Melting point	206 °C
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
solubility	Soluble in water (15 mg/ml)
form	powder
color	White to off-white
Stability	Stable for 2 years from date of purchase as supplied. Solutions in water may be stored at -20°C for up to 1 month.
InChI	1S/C16H17NO4.ClH/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19;/h3-5,11,14-16,18-19H,1-2,6-7H2;1H/t11-,14-,15+,16+;/m0./s1
InChIKey	VUVNTYCHKZBOMV-NVJKKXITSA-N
SMILES	Cl.O[C@H]1C=C2CCN3Cc4cc5OCOc5cc4[C@H]([C@@H]1O)[C@@H]23

Safety Information

Hazard Codes	T
Risk Statements	25
Safety Statements	45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral

Usage And Synthesis

Description

Lycorine (2188-68-3) arrests cell cycle at G2/M phase and induces apoptosis in tumor cells.1 Inhibits human enterovirus 71 replication by blocking elongation of the viral polyprotein during translation and reduces viral cytopathic effects in mice.2 Dose-dependently extends the circadian period length in mammalian cells by enhancing Bmal1 transcription.3 Selectively inhibits human ovarian cancer cell proliferation and neovascularization (IC50=1.2 μM).4A potent SREBF chaperone (SCAP) degrader (Kd=15.24 nM) which acts via an autophagy-independent lysosomal pathway.5

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Lycoris radiata bulbs.

Uses

Lycorine Hydrochloride is the main phenanthridine Amaryllidaceae alkaloid which exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli.

Biochem/physiol Actions

A selective inhibitor of peptidyl transferase center (PTC). In HL-60 (leukemia) cells, lycorine arrests the cell cycle at G2/M and induces apoptosis by a caspase-mediated pathway.

in vivo

Lycorine hydrochloride (0-15 μg; subcutaneous injection; for 14 days; BALB/C nude mice) treatment has an inhibitory effect on melanoma cell-mediated tumor vasculogenic mimicry^[1].

Animal Model:	6- to 8-week-old BALB/C nude mice^[1]
Dosage:	0 μg, 7.5 μg, 15 μg
Administration:	Subcutaneous injection; for 14 days
Result:	Showed an inhibitory effect on melanoma cell-mediated tumor vasculogenic mimicry.

References

[1] GIEDRIUS MILIAUSKAS. Identification of Radical Scavenging Compounds in Rhaponticum carthamoides by Means of LC-DAD-SPE-NMR[J]. Journal of Natural Products , 2005, 68 2: 168-172. DOI:10.1021/np0496901
[2] JIANGNING LIU. Lycorine reduces mortality of human enterovirus 71-infected mice by inhibiting virus replication.[J]. Virology Journal, 2011: 483. DOI:10.1186/1743-422x-8-483
[3] YOSHIAKI ONISHI Y Y Yasuhiro Kawano. Lycorine, a candidate for the control of period length in mammalian cells.[J]. Cellular Physiology and Biochemistry, 2012, 29 3-4: 407-416. DOI:10.1159/000338495
[4] ZHIFEI CAO . Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity[J]. Toxicology letters, 2013, 218 2: Pages 174-185. DOI:10.1016/j.toxlet.2013.01.018
[5] LIANGDE ZHENG. The Paf1 complex transcriptionally regulates the mitochondrial-anchored protein Atg32 leading to activation of mitophagy.[J]. Autophagy, 2019. DOI:10.1080/15548627.2019.1668228

Lycorine hydrochloride

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