Oxophoebine
Oxophoebine is a biologically active oxoaporphine alkaloid and also a DNA topoisomerase inhibitor. Oxophoebine acts as a cytotoxic agent against certain cancer cells. Oxophoebine binds to Measles Virus fusion protein, hemagglutinin and phosphoprotein, and interferes with viral entry, replication and particle assembly processes. Oxophoebine exhibits selective toxicity towards yeast mutants with defects in DNA repair and recombination. Oxophoebine can be used in studies related to measles and coronavirus disease 2019 (COVID-19).
For research use only. We do not sell to patients.
- CAS No.: 109175-37-3
- Formula: C20H15NO6
- Molecular Weight:365.34
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
Oxophoebine does not exhibit significant cytotoxicity against human breast adenocarcinoma MCF7 cells, human nasopharynx carcinoma KB cells, or human small cell lung cancer NCI-H187 cells, with IC50 values >50 μM for all three cell lines[1].
Oxophoebine (100 ns) binds with high affinity to FUP, HMG, and PSP with MM/GBSA binding free energies ranging from −40.68 to −25.37 kcal/mol, exhibits favorable pharmacokinetic properties, and acts as a promising multi-target scaffold for anti-measles virus inhibitor development[2].
Oxophoebine binds to SARS-CoV-2 Mpro with a binding affinity of -7.6 kcal/mol, forming multiple non-covalent interactions with key protease residues[4].
Oxophoebine (48 h) shows selective toxicity against DNA repair and recombination-deficient Saccharomyces cerevisiae strains (rad 52, rad 52.top 1, rad 6) with IC12 values of 6.4 μg/mL, 2.6 μg/mL, and 4.7 μg/mL respectively, while being inactive against the wild-type rad+ strain (IC12 >500 μg/mL)[3].
Oxophoebine is present as a major constituent in the broad-spectrum antibacterial fractionated extract of Annona squamosa leaves, but its direct antibacterial activity is not demonstrated[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 109175-37-3
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Molecular Weight 365.34
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Formula C20H15NO6
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SMILES
O=C1C2=NC=CC3=C(C(OC)=C(C(C4=C1C=C5OCOC5=C4)=C23)OC)OC
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Rayanil KO, et al. The first total syntheses of (±)-norphoebine, dehydrophoebine, oxophoebine, dehydrocrebanine, oxocrebanine and uthongine and their cytotoxicity against three human cancer cell lines. Journal of Asian natural products research. 2016 Nov;18(11):1042-56. [Content Brief]
[2]. Oloche JJ, et al. Molecular Modeling Identification of Key Secondary Metabolites from Xylopia aethiopica as Promising Therapeutics Targeting Essential Measles Viral Proteins. Evid Based Complement Alternat Med. 2023 Feb 9;2023:1575358. [Content Brief]
[3]. Harrigan GG, et al. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea. Journal of natural products. 1994 Jan;57(1):68-73. [Content Brief]
[5]. Dholvitayakhun A, et al. Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease. Natural product communications. 2013 Mar;8(3):385-8. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Oxophoebine Related Classifications
HY-N19651 Related Classifications
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- Oxophoebine
- 109175-37-3
- Topoisomerase
- DNA topoisomerase
- Annona squamosa
- Saccharomyces cerevisiae
- human nasopharynx carcinoma KB cells
- measles virus haemagglutinin protein
- human breast adenocarcinoma MCF7 cells
- SARS-CoV-2 Mpro
- measles virus phosphoprotein
- measles virus fusion protein
- human small cell lung cancer NCI-H187 cells
- Inhibitor
- inhibitor
- inhibit