Lycorine hydrochloride CAS 2188-68-3

Introduction：Basic information about Lycorine hydrochloride CAS 2188-68-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Lycorine hydrochloride Basic information

• Product Name: Lycorine hydrochloride
• Synonyms: Lycorine Hydrochloride98%;Licorin hydrochloride;Hydrochloric Lycorine;LYCORIN;(-)-LYCORINE;LYCORINE;1H-[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol,2,4,5,7,12b,12c-hexahydro-, hydrochloride (1:1), (1S,2S,12bS,12cS)-;NARCISSIN(P)
• CAS: 2188-68-3
• MF: C16H17NO4
• MW: 287.31
• Product Categories: Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Peptidyl transferaseCell Signaling and Neuroscience;Enzyme Inhibitors by Enzyme;Gene Regulation and Expression;P to;RNA-Protein Translation Inhibitors
• Mol File: 2188-68-3.mol

Lycorine hydrochloride 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

Lycorine hydrochloride 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).4?A 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 Preparation Products And Raw materials

• Preparation Products: 1H-[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol, 2,4,5,7,12b,12c-hexahydro-, 1-acetate, (1S,2S,12bS,12cS)-