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791056 | 2-OHOA

2-hydroxyoleic acid (sodium salt)

2-OHOA

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2-OHOA

2-hydroxyoleic acid (sodium salt)

2-Hydroxy Oleic Acid is an inducer of cell cycle arrest and apoptosis in several cancer cell lines, including glioma, leukemia, breast and colon cancer lines. 2-Hydroxy Oleic Acid increases sphingomyelin (SM) levels in the membranes of tumor cells, which typically display decreased SM membrane content, and remodeled membranes, compared with normal cells. The compound has no effect on SM levels in non-cancer cells.

Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C18H33NaO3
Percent Composition
C 67.47%;,H,10.38%, Na 7.17%, O 14.98%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
1229114-68-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
320.443
Exact Mass
320.233
Synonyms
Minerval
NaCHOleate
2OHOA
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References

Prajapati R, Gontsarik M, Yaghmur A, Salentinig S. pH-Responsive Nano-Self-Assemblies of the Anticancer Drug 2-Hydroxyoleic Acid. Langmuir. 2019 Jun 18;35(24):7954-7961. doi: 10.1021/acs.langmuir.9b00838. Epub 2019 May 31.

 PubMed ID: 31150248

Llado, V., D.J. Lopez, M. Ibarguren, M. Alonso, J.B. Soriano, P.V. Escriba, and X. Busquets. (2014). Regulation of the cancer cell membrane lipid composition by NaCHOleate: Effects on cell signaling and therapeutical relevance in glioma. Biochim Biophys Acta [PubMed]

 PubMed ID: 24525074

Khmelinskaia, A., M. Ibarguren, R.F. de Almeida, D.J. Lopez, V.A. Paixao, H. Ahyayauch, F.M. Goni, and P.V. Escriba. (2014). Changes in Membrane Organization upon Spontaneous Insertion of 2-Hydroxylated Unsaturated Fatty Acids in the Lipid Bilayer. Langmuir [PubMed]

PubMed ID: 24490728

Piotto, S., S. Concilio, E. Bianchino, P. Iannelli, D.J. Lopez, S. Teres, M. Ibarguren, G. Barcelo-Coblijn, M.L. Martin, F. Guardiola-Serrano, M. Alonso-Sande, S.S. Funari, X. Busquets, and P.V. Escriba. (2014). Differential effect of 2-hydroxyoleic acid enantiomers on protein (sphingomyelin synthase) and lipid (membrane) targets. Biochim Biophys Acta [PubMed]

 PubMed ID: 24412218

Martin, M.L., G. Liebisch, S. Lehneis, G. Schmitz, M. Alonso-Sande, J. Bestard-Escalas, D.H. Lopez, J.M. Garcia-Verdugo, M. Soriano-Navarro, X. Busquets, P.V. Escriba, and G. Barcelo-Coblijn. (2013). Sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells. J Lipid Res 54:1457-65. [PubMed]

 PubMed ID: 23471028

Martin, M.L., G. Barcelo-Coblijn, R.F. de Almeida, M.A. Noguera-Salva, S. Teres, M. Higuera, G. Liebisch, G. Schmitz, X. Busquets, and P.V. Escriba. (2013). The role of membrane fatty acid remodeling in the antitumor mechanism of action of 2-hydroxyoleic acid. Biochim Biophys Acta 1828:1405-13. [PubMed]

 PubMed ID: 23360770

Marcilla-Etxenike, A., M.L. Martin, M.A. Noguera-Salva, J.M. Garcia-Verdugo, M. Soriano-Navarro, I. Dey, P.V. Escriba, and X. Busquets. (2012). 2-Hydroxyoleic acid induces ER stress and autophagy in various human glioma cell lines. PLoS One 7:e48235 [PubMed]

PubMed ID: 23133576

Teres, S., V. Llado, M. Higuera, G. Barcelo-Coblijn, M.L. Martin, M.A. Noguera-Salva, A. Marcilla-Etxenike, J.M. Garcia-Verdugo, M. Soriano-Navarro, C. Saus, U. Gomez-Pinedo, X. Busquets, and P.V. Escriba. (2012). Normalization of sphingomyelin levels by 2-hydroxyoleic acid induces autophagic cell death of SF767 cancer cells. Autophagy 8:1542-4. [PubMed]

PubMed ID: 22892762

Teres, S., V. Llado, M. Higuera, G. Barcelo-Coblijn, M.L. Martin, M.A. Noguera-Salva, A. Marcilla-Etxenike, J.M. Garcia-Verdugo, M. Soriano-Navarro, C. Saus, U. Gomez-Pinedo, X. Busquets, and P.V. Escriba. (2012). 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy. Proc Natl Acad Sci U S A 109:8489-94 [PubMed]

 PubMed ID: 22586083

Barcelo-Coblijn, G., M.L. Martin, R.F. de Almeida, M.A. Noguera-Salva, A. Marcilla-Etxenike, F. Guardiola-Serrano, A. Luth, B. Kleuser, J.E. Halver, and P.V. Escriba. (2011). Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy. Proc Natl Acad Sci U S A 108:19569-74. [PubMed]

 PubMed ID: 22106271

Llado, V., A. Gutierrez, J. Martinez, J. Casas, S. Teres, M. Higuera, A. Galmes, C. Saus, J. Besalduch, X. Busquets, and P.V. Escriba. (2010). Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med 14:659-70. [PubMed]

 PubMed ID: 19413889
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