Fagaronine Free Base

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

MedKoo CAT#: 414191

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

Description: Fagaronine Free Base is an Antineoplastic Agent

Chemical Structure

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

Theoretical Analysis

MedKoo Cat#: 414191
Name: Fagaronine Free Base
CAS#: 52259-65-1 (free base)
Chemical Formula: C21H20NO4+
Exact Mass: 350.14
Molecular Weight: 350.390
Elemental Analysis: C, 71.99; H, 5.75; N, 4.00; O, 18.26

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.