Date published: 2025-10-15

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Aaptamine (CAS 85547-22-4)

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Alternate Names:
8,9-Dimethoxy-1H-benzo[de][1,6]naphtyridine
Application:
Aaptamine is a spongean alkaloid that can activate the p21 promoter in the absence of p53
CAS Number:
85547-22-4
Purity:
≥97%
Molecular Weight:
228.25
Molecular Formula:
C13H12N2O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Aaptamine is a spongean alkaloid that can activate the p21 promoter in the absence of p53 and can function as a proteasome inhibitor. The compound is a competitive antagonist of AR (alpha-adrenoreceptors) in vascular smooth muscle. Aaptamine can be converted to isoaaptamine, 9-demethylaaptamine, and 4-methylaaptamine, with some of the aaptamine derivatives, such as 9-demethylaaptamine, showing antimicrobial activities. Research suggests that aaptamine can inhibit cancer cell growth and that its cytotoxicity may be due to its ability to intercalate DNA. Aaptamine is an inhibitor of CTRL.


Aaptamine (CAS 85547-22-4) References

  1. Antineoplastic agents 491. Synthetic conversion of aaptamine to isoaaptamine, 9-demethylaaptamine, and 4-methylaaptamine.  |  Pettit, GR., et al. 2004. J Org Chem. 69: 2251-6. PMID: 15049616
  2. Aaptamine, a spongean alkaloid, activates p21 promoter in a p53-independent manner.  |  Aoki, S., et al. 2006. Biochem Biophys Res Commun. 342: 101-6. PMID: 16480688
  3. Antiviral and anticancer optimization studies of the DNA-binding marine natural product aaptamine.  |  Bowling, JJ., et al. 2008. Chem Biol Drug Des. 71: 205-15. PMID: 18251774
  4. Aaptamine, an alkaloid from the sponge Aaptos suberitoides, functions as a proteasome inhibitor.  |  Tsukamoto, S., et al. 2010. Bioorg Med Chem Lett. 20: 3341-3. PMID: 20451377
  5. Antiproliferative effect of aaptamine on human chronic myeloid leukemia K562 cells.  |  Jin, M., et al. 2011. Int J Mol Sci. 12: 7352-9. PMID: 22174603
  6. Activity of aaptamine and two derivatives, demethyloxyaaptamine and isoaaptamine, in cisplatin-resistant germ cell cancer.  |  Dyshlovoy, SA., et al. 2014. J Proteomics. 96: 223-39. PMID: 24269226
  7. The cytotoxic and mechanistic effects of aaptamine on hepatocellular carcinoma.  |  Li, QL., et al. 2015. Anticancer Agents Med Chem. 15: 291-7. PMID: 25403168
  8. Total Synthesis of Aaptamine, Demethyloxyaaptamine, and Their 3-Alkylamino Derivatives.  |  Gao, Y., et al. 2019. Org Lett. 21: 1430-1433. PMID: 30775923
  9. Aaptamine attenuates the proliferation and progression of non-small cell lung carcinoma.  |  Gong, K., et al. 2020. Pharm Biol. 58: 1044-1054. PMID: 33027592
  10. Review on marine sponge alkaloid, aaptamine: A potential antibacterial and anticancer drug.  |  Nadar, VM., et al. 2022. Chem Biol Drug Des. 99: 103-110. PMID: 34331335
  11. Aaptamine - a dual acetyl - and butyrylcholinesterase inhibitor as potential anti-Alzheimer's disease agent.  |  Miao, S., et al. 2022. Pharm Biol. 60: 1502-1510. PMID: 35968601
  12. Antinociceptive Effects of Aaptamine, a Sponge Component, on Peripheral Neuropathy in Rats.  |  Sung, CS., et al. 2023. Mar Drugs. 21: PMID: 36827154
  13. Alpha-adrenoceptor blocking action of aaptamine, a novel marine natural product, in vascular smooth muscle.  |  Ohizumi, Y., et al. 1984. J Pharm Pharmacol. 36: 785-6. PMID: 6150989

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Aaptamine, 1 mg

sc-202899
1 mg
$400.00

Aaptamine, 10 mg

sc-202899A
10 mg
$1900.00