Lycorine HCl | CAS#2188-68-3 | phenanthridine Amaryllidaceae alkaloid

MedKoo Cat#: 598814 | Name: Lycorine HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Lycorine HCl

CAS#2188-68-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 598814

Name: Lycorine HCl

CAS#: 2188-68-3 (HCl)

Chemical Formula: C16H18ClNO4

Exact Mass: 323.0924

Molecular Weight: 323.77

Elemental Analysis: C, 59.36; H, 5.60; Cl, 10.95; N, 4.33; O, 19.77

Price and Availability

Size	Price	Availability	Quantity
1g	USD 285.00	2 weeks
5g	USD 650.00	2 Weeks

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Related CAS #

476-28-8 (free base) 2188-68-3 (HCl) 6150-58-9 (HCl hydrate)

Synonym

Lycorine hydrochloride; Lycorine HCl;

IUPAC/Chemical Name

(1S,2R,3a1S,12bS)-2,3a1,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol hydrochloride

InChi Key

VUVNTYCHKZBOMV-GCXWTACMSA-N

InChi Code

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-;/m1./s1

SMILES Code

O[C@@H]([C@H]1O)C=C(CCN2C3)[C@@H]2[C@@H]1c4c3cc5c(OCO5)c4.Cl

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lycorine hydrochloride is the main active ingredient of the herbal medicine derived from Lycoris radiata (L’Her.) Herb. and is also a melanoma vasculogenic inhibitor and has anti-tumor activity. Lycorine hydrochloride effectively inhibits mitotic proliferation of Hey1B cells (IC50 of 1.2 μM).

In vitro activity:

The present study further revealed that lycorine can inhibit the proliferation of K562 cells. This study evaluated the cell cycle distribution after lycorine treatment and found that lycorine causes cell-cycle arrest in the G0/G1 phase. After lycorine treatment, cyclin D1 and cyclin-dependent kinase 4 expressions were inhibited and retinoblastoma protein phosphorylation was reduced. Lycorine treatment also significantly upregulated the expression of p53 and its target gene product, p21. Reference: Cancer Cell Int. 2012 Nov 23;12(1):49. https://pubmed.ncbi.nlm.nih.gov/23176676/

In vivo activity:

HL-60 cells (5 x 10(6)) were inoculated i.v. into severe combined immuno-deficiency (SCID) mice after these mice had been irradiated (total body receiving 200cGy chi irradiation). Lycorine (5 or 10 mg/kg/day i.p.) was found to decrease the percentages of immature granular leukocytes and of monocytes among the peripheral blood cells, and the mean survival time of both lycorine-treated groups was longer than that of the control group. Compared with the asynchronous and cytosine arabinoside- (Ara-C) treated (20 mg/kg/day i.p.) group, treatment with lycorine was more effective. Lycorine was also found to alleviate the infiltration of tumor cells into the liver, bone, and marrow. Reference: Biomed Pharmacother. 2007 May;61(4):229-34. https://pubmed.ncbi.nlm.nih.gov/17336028/

	Solvent	mg/mL	mM
Solubility
	DMSO	45.0	138.99
	Water	16.7	51.49

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 323.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Liu R, Cao Z, Tu J, Pan Y, Shang B, Zhang G, Bao M, Zhang S, Yang P, Zhou Q. Lycorine hydrochloride inhibits metastatic melanoma cell-dominant vasculogenic mimicry. Pigment Cell Melanoma Res. 2012 Sep;25(5):630-8. doi: 10.1111/j.1755-148X.2012.01036.x. PMID: 22781316. 2. Li L, Dai HJ, Ye M, Wang SL, Xiao XJ, Zheng J, Chen HY, Luo YH, Liu J. Lycorine induces cell-cycle arrest in the G0/G1 phase in K562 cells via HDAC inhibition. Cancer Cell Int. 2012 Nov 23;12(1):49. doi: 10.1186/1475-2867-12-49. PMID: 23176676; PMCID: PMC3537594. 3. Cao Z, Yu D, Fu S, Zhang G, Pan Y, Bao M, Tu J, Shang B, Guo P, Yang P, Zhou Q. Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity. Toxicol Lett. 2013 Apr 12;218(2):174-85. doi: 10.1016/j.toxlet.2013.01.018. Epub 2013 Jan 31. PMID: 23376478. 4. Liu J, Li Y, Tang LJ, Zhang GP, Hu WX. Treatment of lycorine on SCID mice model with human APL cells. Biomed Pharmacother. 2007 May;61(4):229-34. doi: 10.1016/j.biopha.2007.01.003. Epub 2007 Feb 12. PMID: 17336028; PMCID: PMC7126558.

In vitro protocol:

In vivo protocol:

1. Cao Z, Yu D, Fu S, Zhang G, Pan Y, Bao M, Tu J, Shang B, Guo P, Yang P, Zhou Q. Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity. Toxicol Lett. 2013 Apr 12;218(2):174-85. doi: 10.1016/j.toxlet.2013.01.018. Epub 2013 Jan 31. PMID: 23376478. 2. Liu J, Li Y, Tang LJ, Zhang GP, Hu WX. Treatment of lycorine on SCID mice model with human APL cells. Biomed Pharmacother. 2007 May;61(4):229-34. doi: 10.1016/j.biopha.2007.01.003. Epub 2007 Feb 12. PMID: 17336028; PMCID: PMC7126558.

H^ 1: Chen BY, Du ZH, Zeng FD, Hu CJ, Ma GE, Hong SH. [Hypotensive effect of dihydrolycorine]. Zhongguo Yao Li Xue Bao. 1993 Jan;14(1):45-9. Chinese. PubMed PMID: 8503287.