pivalyloxymethyl butyrate

• CAT Number: M024304
• CAS Number: 122110-53-6
• Molecular Formula: C10H18O4
• Molecular Weight: 202.25
• Purity: ≥95%
• Target: HDAC inhibitor
• Storage: -20°C
• IUPAC Name: butanoyloxymethyl 2,2-dimethylpropanoate
• InChI: InChI=1S/C10H18O4/c1-5-6-8(11)13-7-14-9(12)10(2,3)4/h5-7H2,1-4H3
• InChIKey: GYKLFBYWXZYSOW-UHFFFAOYSA-N
• SMILES: CCCC(=O)OCOC(=O)C(C)(C)C

Pivanex, also known as AN-9, is a histone deacetylase inhibitor analog of butyric acid that causes apoptosis of cancer cells through signaling cellular differentiation. AN-9 exerts a significant anticancer activity in vitro and in vivo.

Reference

1:Mol Pharmacol. 2000 Jul;58(1):27-36. Anticancer derivative of butyric acid (Pivalyloxymethyl butyrate) specifically potentiates the cytotoxicity of doxorubicin and daunorubicin through the suppression of microsomal glycosidic activity.Niitsu N,Kasukabe T,Yokoyama A,Okabe-Kado J,Yamamoto-Yamaguchi Y,Umeda M,Honma Y, PMID: 10860924 Abstract: Pivalyloxymethyl butyrate (AN9) is an anticancer derivative of butyric acid. In this study, doxorubicin (DXR) and AN9 synergistically inhibited the growth of lymphoma and lung carcinoma cells, whereas there was no synergy between AN9 and antimetabolites. AN9 did not affect the intracellular uptake of DXR. Among anthracyclines and their derivatives, the synergistic effect was prominent in compounds with a daunosamine moiety, suggesting that AN9 may affect the catabolism of these compounds. The degradation of DXR in the extract from AN9-treated cells was much less than that in extract from untreated cells. AN9 did not directly inhibit the enzyme activity but rather suppressed expression of the enzyme. With respect to the expression of drug resistance-related genes, there was no significant difference between untreated and AN9-treated cells. However, AN9 significantly down-regulated the levels NADPH-cytochrome P450 reductase and DT-diaphorase mRNA in the presence of DXR but not the level of xanthine oxidase mRNA. The enhancement of the sensitivity to anthracyclines was closely associated with the suppression of the mRNA expression.