AaptamineA spongean alkaloid that can activate the p21 promoter in the absence of p53

Aaptamine (CAS 85547-22-4)

Aaptamine | CAS 85547-22-4 is rated 5.0 out of 5 by 1.
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Synonym: 8,9-Dimethoxy-1H-benzo[de][1,6]naphtyridine
Application: 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
* Refer to Certificate of Analysis for lot specific data (including water content).
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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 (α-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.


References

1. Ohizumi, Y., et al. 1984. J. Pharm. Pharmacol. 36: 785-786. PMID: 6150989
2. Pettit, G.R., et al. 2004. J. Org. Chem. 69: 2251-2256. PMID: 15049616
3. Aoki, S., et al. 2006. Biochem. Biophys. Res. Commun. 342: 101-106. PMID: 16480688
4. Bowling, J.J., et al. 2008. Chem Biol Drug Des. 71: 205-215. PMID: 18251774
5. Tsukamoto, S., et al. 2010. Bioorg. Med. Chem. Lett. 20: 3341-3343. PMID: 20451377

Physical State :
Solid
Derived From :
Aaptos aaptos
Solubility :
Soluble in DMSO, and 100% ethanol.
Storage :
Store at -20° C
Melting Point :
145.40° C (Predicted)
Boiling Point :
420.58° C at 760 mmHg (Predicted)
Density :
1.25 g/mL (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
IC50 :
A549: IC50 = 12.27 µM (human); P388: IC50 = 2.63 µM (mouse); HT-29: IC50 = 30.23 µM (human); Hela: IC50 = 65.72 µM (human); Proteasome (chymotrypsin-like): IC50 = 7.01 µM
pK Values :
pKb: 6.06 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
122826
SMILES :
COC1=C(C2=NC=CC3=C2C(=C1)C=CN3)OC

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from Aoki et al Aoki et al. (PubMed ID 16480688) found that Aaptamine activated the p21 promoter in a p53-independent manner. -SCBT Publication Review
Date published: 2015-05-26
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