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MedKoo Cat#: 414191 | Name: Fagaronine Free Base

Description:

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

Fagaronine Free Base is an Antineoplastic Agent

Chemical Structure

Fagaronine Free Base
Fagaronine Free Base
CAS#52259-65-1 (free base)

Theoretical Analysis

MedKoo Cat#: 414191

Name: Fagaronine Free Base

CAS#: 52259-65-1 (free base)

Chemical Formula: C21H20NO4+

Exact Mass: 350.1387

Molecular Weight: 350.39

Elemental Analysis: C, 71.99; H, 5.75; N, 4.00; O, 18.26

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
52259-65-1 (free base) 52259-64-0 (chloride)
Synonym
Fagaronine Free Base; BRN1554609; BRN-1554609; BRN 1554609
IUPAC/Chemical Name
Benzo(c)phenanthridinium, 2-hydroxy-3,8,9-trimethoxy-5-methyl-
InChi Key
OOKZVPUCASIEBL-UHFFFAOYSA-O
InChi Code
InChI=1S/C21H19NO4/c1-22-11-13-8-19(25-3)20(26-4)9-15(13)14-6-5-12-7-17(23)18(24-2)10-16(12)21(14)22/h5-11H,1-4H3/p+1
SMILES Code
C[N+]1=CC2=CC(OC)=C(OC)C=C2C3=C1C4=CC(OC)=C(O)C=C4C=C3
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 350.39 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: Larsen AK, Grondard L, Couprie J, Desoize B, Comoe L, Jardillier JC, Riou JF. The antileukemic alkaloid fagaronine is an inhibitor of DNA topoisomerases I and II. Biochem Pharmacol. 1993 Oct 19;46(8):1403-12. doi: 10.1016/0006-2952(93)90105-6. PMID: 8240389. 2: Rivaud M, Mendoza A, Sauvain M, Valentin A, Jullian V. Short synthesis and antimalarial activity of fagaronine. Bioorg Med Chem. 2012 Aug 1;20(15):4856-61. doi: 10.1016/j.bmc.2012.05.061. Epub 2012 Jun 5. PMID: 22766218. 3: Dupont C, Couillerot E, Gillet R, Caron C, Zeches-Hanrot M, Riou JF, Trentesaux C. The benzophenanthridine alkaloid fagaronine induces erythroleukemic cell differentiation by gene activation. Planta Med. 2005 Jun;71(6):489-94. doi: 10.1055/s-2005-864147. PMID: 15971117. 4: Wang LK, Johnson RK, Hecht SM. Inhibition of topoisomerase I function by nitidine and fagaronine. Chem Res Toxicol. 1993 Nov-Dec;6(6):813-8. doi: 10.1021/tx00036a010. PMID: 8117920. 5: Ouchani F, Jeanne A, Thevenard J, Helesbeux JJ, Wahart A, Letinois I, Duval O, Martiny L, Charpentier E, Devy J. Ethoxyfagaronine, a synthetic analogue of fagaronine that inhibits vascular endothelial growth factor-1, as a new anti- angiogeneic agent. Invest New Drugs. 2015 Feb;33(1):75-85. doi: 10.1007/s10637-014-0184-4. Epub 2014 Nov 19. PMID: 25404487. 6: Fleury F, Sukhanova A, Ianoul A, Devy J, Kudelina I, Duval O, Alix AJ, Jardillier JC, Nabiev I. Molecular determinants of site-specific inhibition of human DNA topoisomerase I by fagaronine and ethoxidine. Relation to DNA binding. J Biol Chem. 2000 Feb 4;275(5):3501-9. doi: 10.1074/jbc.275.5.3501. PMID: 10652345. 7: Messmer WM, Tin-Wa M, Fong HH, Bevelle C, Farnsworth NR, Abraham DJ, Trojánek J. Fagaronine, a new tumor inhibitor isolated from Fagara zanthoxyloides Lam. (Rutaceae). J Pharm Sci. 1972 Nov;61(11):1858-9. doi: 10.1002/jps.2600611145. PMID: 4652672. 8: Benoist H, Comoe L, Joly P, Carpentier Y, Desplaces A, Dufer J. Comparative effects of fagaronine, adriamycin and aclacinomycin on K562 cell sensitivity to natural-killer-mediated lysis. Lack of agreement between alteration of transferrin receptor and CD15 antigen expressions and induction of resistance to natural killer. Cancer Immunol Immunother. 1989;30(5):289-94. doi: 10.1007/BF01744896. PMID: 2624922. 9: Yao T, Guo Z, Liang X, Qi L. Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine. J Org Chem. 2018 Nov 2;83(21):13370-13380. doi: 10.1021/acs.joc.8b02154. Epub 2018 Oct 12. PMID: 30265534. 10: Pérez-Chiesa Y, Narváez Z. Evaluation of genotoxicity of the indenoisoquinoline analogues of fagaronine and nitidine in Drosophila melanogaster. Mutat Res. 1993 Apr;301(4):207-12. doi: 10.1016/0165-7992(93)90059-5. PMID: 7680753.