Aaptamine

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

MedKoo CAT#: 571291

CAS#: 85547-22-4

Description: Aaptamine is a natural biochemical isolated from sea sponge. It has an anti-proliferative effect on hepatocellular carcinoma (HCC) and hepatocarcinogenesis. Aaptamine treatment leads to cell cycle arrest in HCC cells.


Price and Availability

Size
Price

Size
Price

Size
Price

Aaptamine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 571291
Name: Aaptamine
CAS#: 85547-22-4
Chemical Formula: C13H12N2O2
Exact Mass: 228.0899
Molecular Weight: 228.25
Elemental Analysis: C, 68.41; H, 5.30; N, 12.27; O, 14.02


Synonym: Aaptamine

IUPAC/Chemical Name: 1H-Benzo(de)(1,6)naphthyridine, 8,9-dimethoxy-

InChi Key: IVXSXOFPZFVZTM-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H12N2O2/c1-16-10-7-8-3-5-14-9-4-6-15-12(11(8)9)13(10)17-2/h3-7,15H,1-2H3

SMILES Code: COC1=C2C3=C(N=CC=C3C=C1OC)C=CN2


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Li QL, Zhang PP, Wang PQ, Yu HB, Sun F, Hu WZ, Wu WH, Zhang X, Chen F, Chu ZY, Zhang JP, Chen SS, Lin HW. The cytotoxic and mechanistic effects of aaptamine on hepatocellular carcinoma. Anticancer Agents Med Chem. 2015;15(3):291-7. PubMed PMID: 25403168.

2: Pham CD, Hartmann R, Müller WE, de Voogd N, Lai D, Proksch P. Aaptamine derivatives from the Indonesian sponge Aaptos suberitoides. J Nat Prod. 2013 Jan 25;76(1):103-6. doi: 10.1021/np300794b. Epub 2013 Jan 2. PubMed PMID: 23282083.

3: Kim MJ, Woo SW, Kim MS, Park JE, Hwang JK. Anti-photoaging effect of aaptamine in UVB-irradiated human dermal fibroblasts and epidermal keratinocytes. J Asian Nat Prod Res. 2014 Dec;16(12):1139-47. doi: 10.1080/10286020.2014.983092. Epub 2014 Dec 3. PubMed PMID: 25465718.

4: Yu HB, Yang F, Sun F, Li J, Jiao WH, Gan JH, Hu WZ, Lin HW. Aaptamine derivatives with antifungal and anti-HIV-1 activities from the South China Sea sponge Aaptos aaptos. Mar Drugs. 2014 Dec 16;12(12):6003-13. doi: 10.3390/md12126003. PubMed PMID: 25532563; PubMed Central PMCID: PMC4278215.

5: Yu HB, Yang F, Sun F, Ma GY, Gan JH, Hu WZ, Han BN, Jiao WH, Lin HW. Cytotoxic aaptamine derivatives from the South China Sea sponge Aaptos aaptos. J Nat Prod. 2014 Sep 26;77(9):2124-9. doi: 10.1021/np500583z. Epub 2014 Sep 11. PubMed PMID: 25211032.

6: Dyshlovoy SA, Venz S, Shubina LK, Fedorov SN, Walther R, Jacobsen C, Stonik VA, Bokemeyer C, Balabanov S, Honecker F. Activity of aaptamine and two derivatives, demethyloxyaaptamine and isoaaptamine, in cisplatin-resistant germ cell cancer. J Proteomics. 2014 Jan 16;96:223-39. doi: 10.1016/j.jprot.2013.11.009. Epub 2013 Nov 21. PubMed PMID: 24269226.

7: Gan JH, Hu WZ, Yu HB, Yang F, Cao MX, Shi HJ, Kang YF, Han BN. Three new aaptamine derivatives from the South China Sea sponge Aaptos aaptos. J Asian Nat Prod Res. 2015;17(12):1231-8. doi: 10.1080/10286020.2015.1118465. Epub 2015 Dec 24. PubMed PMID: 26699877.

8: Jin M, Zhao W, Zhang Y, Kobayashi M, Duan H, Kong D. Antiproliferative effect of aaptamine on human chronic myeloid leukemia K562 cells. Int J Mol Sci. 2011;12(11):7352-9. doi: 10.3390/ijms12117352. Epub 2011 Oct 26. PubMed PMID: 22174603; PubMed Central PMCID: PMC3233409.

9: Liu C, Tang X, Li P, Li G. Suberitine A-D, four new cytotoxic dimeric aaptamine alkaloids from the marine sponge Aaptos suberitoides. Org Lett. 2012 Apr 20;14(8):1994-7. doi: 10.1021/ol3004589. Epub 2012 Apr 3. PubMed PMID: 22472093.

10: Dyshlovoy SA, Naeth I, Venz S, Preukschas M, Sievert H, Jacobsen C, Shubina LK, Gesell Salazar M, Scharf C, Walther R, Krepstakies M, Priyadarshini P, Hauber J, Fedorov SN, Bokemeyer C, Stonik VA, Balabanov S, Honecker F. Proteomic profiling of germ cell cancer cells treated with aaptamine, a marine alkaloid with antiproliferative activity. J Proteome Res. 2012 Apr 6;11(4):2316-30. doi: 10.1021/pr300170p. Epub 2012 Mar 28. PubMed PMID: 22409352.

11: Funk F, Krüger K, Henninger C, Wätjen W, Proksch P, Thomale J, Fritz G. Spongean alkaloids protect rat kidney cells against cisplatin-induced cytotoxicity. Anticancer Drugs. 2014 Sep;25(8):917-29. doi: 10.1097/CAD.0000000000000119. PubMed PMID: 24820908.

12: Pettit GR, Hoffmann H, Herald DL, McNulty J, Murphy A, Higgs KC, Hamel E, Lewin NE, Pearce LV, Blumberg PM, Pettit RK, Knight JC. Antineoplastic agents 491. Synthetic conversion of aaptamine to isoaaptamine, 9-demethylaaptamine, and 4-methylaaptamine. J Org Chem. 2004 Apr 2;69(7):2251-6. PubMed PMID: 15049616.

13: Bowling JJ, Pennaka HK, Ivey K, Wahyuono S, Kelly M, Schinazi RF, Valeriote FA, Graves DE, Hamann MT. Antiviral and anticancer optimization studies of the DNA-binding marine natural product aaptamine. Chem Biol Drug Des. 2008 Mar;71(3):205-15. doi: 10.1111/j.1747-0285.2008.00628.x. PubMed PMID: 18251774; PubMed Central PMCID: PMC4918911.

14: Dyshlovoy SA, Fedorov SN, Shubina LK, Kuzmich AS, Bokemeyer C, Keller-von Amsberg G, Honecker F. Aaptamines from the marine sponge Aaptos sp. display anticancer activities in human cancer cell lines and modulate AP-1-, NF-κB-, and p53-dependent transcriptional activity in mouse JB6 Cl41 cells. Biomed Res Int. 2014;2014:469309. doi: 10.1155/2014/469309. Epub 2014 Jul 23. PubMed PMID: 25215281; PubMed Central PMCID: PMC4158141.

15: Tsukamoto S, Yamanokuchi R, Yoshitomi M, Sato K, Ikeda T, Rotinsulu H, Mangindaan RE, de Voogd NJ, van Soest RW, Yokosawa H. Aaptamine, an alkaloid from the sponge Aaptos suberitoides, functions as a proteasome inhibitor. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3341-3. doi: 10.1016/j.bmcl.2010.04.029. Epub 2010 Apr 14. PubMed PMID: 20451377.

16: Diers JA, Bowling JJ, Duke SO, Wahyuono S, Kelly M, Hamann MT. Zebra mussel antifouling activity of the marine natural product aaptamine and analogs. Mar Biotechnol (NY). 2006 Jul-Aug;8(4):366-72. Epub 2006 May 26. PubMed PMID: 16718618; PubMed Central PMCID: PMC4917205.

17: Aoki S, Kong D, Suna H, Sowa Y, Sakai T, Setiawan A, Kobayashi M. Aaptamine, a spongean alkaloid, activates p21 promoter in a p53-independent manner. Biochem Biophys Res Commun. 2006 Mar 31;342(1):101-6. Epub 2006 Feb 3. PubMed PMID: 16480688.

18: Shubina LK, Kalinovsky AI, Fedorov SN, Radchenko OS, Denisenko VA, Dmitrenok PS, Dyshlovoy SA, Krasokhin VB, Stonik VA. Aaptamine alkaloids from the Vietnamese sponge Aaptos sp. Nat Prod Commun. 2009 Aug;4(8):1085-8. PubMed PMID: 19768988.

19: Arai M, Han C, Yamano Y, Setiawan A, Kobayashi M. Aaptamines, marine spongean alkaloids, as anti-dormant mycobacterial substances. J Nat Med. 2014 Apr;68(2):372-6. doi: 10.1007/s11418-013-0811-y. Epub 2014 Jan 12. PubMed PMID: 24414399.

20: Ohizumi Y, Kajiwara A, Nakamura H, Kobayashi J. Alpha-adrenoceptor blocking action of aaptamine, a novel marine natural product, in vascular smooth muscle. J Pharm Pharmacol. 1984 Nov;36(11):785-6. PubMed PMID: 6150989.