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MedKoo Cat#: 414466 | Name: Liriodenine Free Base
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Description:

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

Liriodenine Free Base is an alcaloid that has a wide range of biological activities, including antimicrobial, anticancer, cardiovascular effects and affinity for some receptors, is a promising potential drug candidate for the treatment of multiple ailments.

Chemical Structure

Liriodenine Free Base
CAS#475-75-2 (free base)

Theoretical Analysis

MedKoo Cat#: 414466

Name: Liriodenine Free Base

CAS#: 475-75-2 (free base)

Chemical Formula: C17H9NO3

Exact Mass: 275.0582

Molecular Weight: 275.26

Elemental Analysis: C, 74.18; H, 3.30; N, 5.09; O, 17.44

Price and Availability

Size Price Availability Quantity
5mg USD 850.00 2 Weeks
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Related CAS #
475-75-2 (free base) 55974-07-7 (methiodide)
Synonym
Liriodenine Free Base; CCRIS1549; CCRIS-1549; CCRIS 1549; NSC93681; NSC-93681; NSC 93681
IUPAC/Chemical Name
8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-one (9CI)
InChi Key
MUMCCPUVOAUBAN-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2
SMILES Code
O=C1C2=CC=CC=C2C3=C4OCOC4=CC5=CC=NC1=C53
Appearance
Solid powder
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 275.26 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.

Recalculate based on batch purity %
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
1: Wu G, Chen G, Zhou J, Zhu H, Chu J, Zhang F. Liriodenine enhances radiosensitivity in esophageal cancer ECA-109 cells by inducing apoptosis and G2/M arrest. Oncol Lett. 2018 Oct;16(4):5020-5026. doi: 10.3892/ol.2018.9253. Epub 2018 Aug 2. PMID: 30250568; PMCID: PMC6144705. 2: Vinche ADL, de-la-Cruz-Chacón I, González-Esquinca AR, da Silva JF, Ferreira G, Dos Santos DC, Garces HG, de Oliveira DVM, Marçon C, Cavalcante RS, Mendes RP. Antifungal activity of liriodenine on agents of systemic mycoses, with emphasis on the genus Paracoccidioides. J Venom Anim Toxins Incl Trop Dis. 2020 Oct 28;26:e20200023. doi: 10.1590/1678-9199-JVATITD-2020-0023. PMID: 33193751; PMCID: PMC7595607. 3: De la Cruz-Chacón I, González-Esquinca AR, Guevara Fefer P, Jímenez Garcia LF. Liriodenine, early antimicrobial defence in Annona diversifolia. Z Naturforsch C J Biosci. 2011 Jul-Aug;66(7-8):377-84. doi: 10.1515/znc-2011-7-809. PMID: 21950162. 4: Li ZH, Gao J, Hu PH, Xiong JP. Anticancer effects of liriodenine on the cell growth and apoptosis of human breast cancer MCF-7 cells through the upregulation of p53 expression. Oncol Lett. 2017 Aug;14(2):1979-1984. doi: 10.3892/ol.2017.6418. Epub 2017 Jun 19. PMID: 28781641; PMCID: PMC5530144. 5: de la Cruz Chacón I, González-Esquinca AR. Liriodenine alkaloid in Annona diversifolia during early development. Nat Prod Res. 2012;26(1):42-9. doi: 10.1080/14786419.2010.533373. Epub 2011 Jul 27. PMID: 21790492. 6: Li L, Xu Y, Wang B. Liriodenine induces the apoptosis of human laryngocarcinoma cells via the upregulation of p53 expression. Oncol Lett. 2015 Mar;9(3):1121-1127. doi: 10.3892/ol.2014.2834. Epub 2014 Dec 29. PMID: 25663867; PMCID: PMC4314988. 7: Nordin N, Majid NA, Hashim NM, Rahman MA, Hassan Z, Ali HM. Liriodenine, an aporphine alkaloid from Enicosanthellum pulchrum, inhibits proliferation of human ovarian cancer cells through induction of apoptosis via the mitochondrial signaling pathway and blocking cell cycle progression. Drug Des Devel Ther. 2015 Mar 10;9:1437-48. doi: 10.2147/DDDT.S77727. PMID: 25792804; PMCID: PMC4362660. 8: Hsieh TJ, Liu TZ, Chern CL, Tsao DA, Lu FJ, Syu YH, Hsieh PY, Hu HS, Chang TT, Chen CH. Liriodenine inhibits the proliferation of human hepatoma cell lines by blocking cell cycle progression and nitric oxide-mediated activation of p53 expression. Food Chem Toxicol. 2005 Jul;43(7):1117-26. doi: 10.1016/j.fct.2005.03.002. PMID: 15833387. 9: Chang HC, Chang FR, Wu YC, Lai YH. Anti-cancer effect of liriodenine on human lung cancer cells. Kaohsiung J Med Sci. 2004 Aug;20(8):365-71. doi: 10.1016/S1607-551X(09)70172-X. PMID: 15473647. 10: Woo SH, Reynolds MC, Sun NJ, Cassady JM, Snapka RM. Inhibition of topoisomerase II by liriodenine. Biochem Pharmacol. 1997 Aug 15;54(4):467-73. doi: 10.1016/s0006-2952(97)00198-6. PMID: 9313773.

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