Sampangine

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

MedKoo CAT#: 461750

CAS#: 116664-93-8

Description: Sampangine is a cananga tree alkaloid with antifungal activity.


Chemical Structure

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Sampangine
CAS# 116664-93-8

Theoretical Analysis

MedKoo Cat#: 461750
Name: Sampangine
CAS#: 116664-93-8
Chemical Formula: C15H8N2O
Exact Mass: 232.0637
Molecular Weight: 232.24
Elemental Analysis: C, 77.58; H, 3.47; N, 12.06; O, 6.89

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.

Request quote for custom synthesis

Synonym: Sampangine;

IUPAC/Chemical Name: 7H-naphtho[1,2,3-ij][2,7]naphthyridin-7-one

InChi Key: BWQKHOMAOVUASZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H8N2O/c18-15-11-4-2-1-3-10(11)13-12-9(5-7-16-13)6-8-17-14(12)15/h1-8H

SMILES Code: O=C1C2=C(C=CC=C2)C3=NC=CC4=CC=NC1=C43

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: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 232.24 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

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Reconstitution Calculator

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1: Mahdi F, Morgan JB, Liu W, Agarwal AK, Jekabsons MB, Liu Y, Zhou YD, Nagle DG. Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates. J Nat Prod. 2015 Dec 24;78(12):3018-23. doi: 10.1021/acs.jnatprod.5b00819. Epub 2015 Dec 4. PubMed PMID: 26637046.

2: Jiang Z, Liu N, Dong G, Jiang Y, Liu Y, He X, Huang Y, He S, Chen W, Li Z, Yao J, Miao Z, Zhang W, Sheng C. Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans. Bioorg Med Chem Lett. 2014 Sep 1;24(17):4090-4. doi: 10.1016/j.bmcl.2014.07.064. Epub 2014 Aug 1. PubMed PMID: 25115626.

3: Jiang Z, Liu N, Hu D, Dong G, Miao Z, Yao J, He H, Jiang Y, Zhang W, Wang Y, Sheng C. The discovery of novel antifungal scaffolds by structural simplification of the natural product sampangine. Chem Commun (Camb). 2015 Oct 7;51(78):14648-51. doi: 10.1039/c5cc05699c. PubMed PMID: 26289663.

4: Huang Z, Chen K, Xu T, Zhang J, Li Y, Li W, Agarwal AK, Clark AM, Phillips JD, Pan X. Sampangine inhibits heme biosynthesis in both yeast and human. Eukaryot Cell. 2011 Nov;10(11):1536-44. doi: 10.1128/EC.05170-11. Epub 2011 Sep 9. PubMed PMID: 21908598; PubMed Central PMCID: PMC3209050.

5: Claes P, Cappoen D, Mbala BM, Jacobs J, Mertens B, Mathys V, Verschaeve L, Huygen K, De Kimpe N. Synthesis and antimycobacterial activity of analogues of the bioactive natural products sampangine and cleistopholine. Eur J Med Chem. 2013 Sep;67:98-110. doi: 10.1016/j.ejmech.2013.06.010. Epub 2013 Jun 18. PubMed PMID: 23850570.

6: Agarwal AK, Xu T, Jacob MR, Feng Q, Lorenz MC, Walker LA, Clark AM. Role of heme in the antifungal activity of the azaoxoaporphine alkaloid sampangine. Eukaryot Cell. 2008 Feb;7(2):387-400. Epub 2007 Dec 21. PubMed PMID: 18156292; PubMed Central PMCID: PMC2238161.

7: Kluza J, Mazinghien R, Degardin K, Lansiaux A, Bailly C. Induction of apoptosis by the plant alkaloid sampangine in human HL-60 leukemia cells is mediated by reactive oxygen species. Eur J Pharmacol. 2005 Nov 21;525(1-3):32-40. Epub 2005 Nov 11. PubMed PMID: 16289142.

8: Kluza J, Clark AM, Bailly C. Apoptosis induced by the alkaloid sampangine in HL-60 leukemia cells: correlation between the effects on the cell cycle progression and changes of mitochondrial potential. Ann N Y Acad Sci. 2003 Dec;1010:331-4. PubMed PMID: 15033745.

9: Orabi KY, Walker LA, Clark AM, Hufford CD. Characterization of the major metabolite of sampangine in rats. J Nat Prod. 2000 May;63(5):685-7. PubMed PMID: 10843589.

10: Lorenzo VP, Lúcio AS, Scotti L, Tavares JF, Filho JM, Lima TK, Rocha JD, Scotti MT. Structure- and Ligand-Based Approaches to Evaluate Aporphynic Alkaloids from Annonaceae as Multi-Target Agent Against Leishmania donovani. Curr Pharm Des. 2016;22(34):5196-5203. Review. PubMed PMID: 27174814.

11: Orabi KY, Li E, Clark AM, Hufford CD. Microbial transformation of sampangine. J Nat Prod. 1999 Jul;62(7):988-92. PubMed PMID: 10425122.

12: Vasilevsky SF, Baranov DS, Mamatyuk VI, Gatilov YV, Alabugin IV. An unexpected rearrangement that disassembles alkyne moiety through formal nitrogen atom insertion between two acetylenic carbons and related cascade transformations: new approach to Sampangine derivatives and polycyclic aromatic amides. J Org Chem. 2009 Aug 21;74(16):6143-50. doi: 10.1021/jo9008904. PubMed PMID: 19585968.

13: Mink K, Bracher F. Hetero analogues of the antimicrobial alkaloids cleistopholine and sampangine. Arch Pharm (Weinheim). 2007 Aug;340(8):429-33. PubMed PMID: 17628034.

14: Sharma V, Sharma PC, Kumar V. A mini review on pyridoacridines: Prospective lead compounds in medicinal chemistry. J Adv Res. 2015 Jan;6(1):63-71. doi: 10.1016/j.jare.2014.11.002. Epub 2014 Nov 15. Review. PubMed PMID: 25685544; PubMed Central PMCID: PMC4293674.

15: Muhammad I, Dunbar DC, Takamatsu S, Walker LA, Clark AM. Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha. J Nat Prod. 2001 May;64(5):559-62. PubMed PMID: 11374943.

16: Lúcio AS, Almeida JR, Barbosa-Filho JM, Pita JC, Branco MV, Diniz Mde F, Agra Mde F, da-Cunha EV, da Silva MS, Tavares JF. Azaphenanthrene alkaloids with antitumoral activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae). Molecules. 2011 Aug 22;16(8):7125-31. doi: 10.3390/molecules16087125. PubMed PMID: 21860364.

17: Fei N, Yin H, Wang S, Wang H, Yao ZJ. CuCl2-promoted 6-endo-dig chlorocyclization and oxidative aromatization cascade: efficient construction of 1-azaanthraquinones from N-propargylaminoquinones. Org Lett. 2011 Aug 19;13(16):4208-11. doi: 10.1021/ol201542h. Epub 2011 Jul 18. PubMed PMID: 21766780.

18: Liu N, Zhong H, Tu J, Jiang Z, Jiang Y, Jiang Y, Jiang Y, Li J, Zhang W, Wang Y, Sheng C. Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors. Eur J Med Chem. 2018 Jan 1;143:1510-1523. doi: 10.1016/j.ejmech.2017.10.043. Epub 2017 Oct 16. PubMed PMID: 29126739.

19: Chen KL, Gan L, Wu ZH, Qin JF, Liao WX, Tang H. 4- Substituted sampangine derivatives: Novel acetylcholinesterase and β-myloid aggregation inhibitors. Int J Biol Macromol. 2018 Feb;107(Pt B):2725-2729. doi: 10.1016/j.ijbiomac.2017.10.157. Epub 2017 Oct 27. PubMed PMID: 29111270.

20: Bracher F. [Polycyclic aromatic alkaloids. 10. Annonaceous alkaloids with antimycotic activity]. Arch Pharm (Weinheim). 1994 Jun;327(6):371-5. German. PubMed PMID: 8048844.