Avrainvillamide  (Synonyms: (+)-Avrainvillamide; CJ-17,665)

Avrainvillamide ((+)-Avrainvillamide) is a naturally occurring alkaloid with antiproliferative effects, binds to the nuclear chaperone nucleophosmin, a proposed oncogenic protein that is overexpressed in many different human tumors. Avrainvillamide affects cell biology both by directly binding NPM1 and Crm1 as well as by inhibiting the association of these proteins with certain native cellular partners. Avrainvillamide, an antibiotic, inhibits growth of multi-agent resistant Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, with MICs of 12.5, 12.5 and 25 μg/ml, respectively^[1][2][3].

Avrainvillamide ((+)-Avrainvillamide) restores nucleolar localization of certain acute myeloid leukemia (AML)-associated mutant forms of NPM1 and provide evidence that this relocalization is mediated by interactions of Avrainvillamide with mutant NPM1 and exportin-1 (Crm1)^[2].
Avrainvillamide ((+)-Avrainvillamide) shows antiproliferative activities in T-47D (breast cancer) cells and LNCaP (prostate cancer) cells with GI₅₀s of 0.33 and 0.42 μM, respectively^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

445.51

C₂₆H₂₇N₃O₄

269741-97-1

O=C1[C@]23[C@@](C(C)(C4=[N+]([O-])C5=C6C(OC(C)(C=C6)C)=CC=C5C4=C3)C)([H])CC7(C(N2)=O)N1CCC7

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [1]. Wulff JE, et al. The natural product avrainvillamide binds to the oncoprotein nucleophosmin. J Am Chem Soc. 2007;129(46):14444-14451.  [Content Brief]

  [2]. Mukherjee H, et al. Interactions of the natural product (+)-avrainvillamide with nucleophosmin and exportin-1 Mediate the cellular localization of nucleophosmin and its AML-associated mutants. ACS Chem Biol. 2015;10(3):855-863.  [Content Brief]

  [3]. Sugie Y, et al. A new antibiotic CJ-17,665 from Aspergillus ochraceus. J Antibiot (Tokyo). 2001;54(11):911-916.  [Content Brief]