Chemistry:Phorbol 12,13-dibutyrate
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| Names | |
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| Preferred IUPAC name
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulene-9,9a-diyl dibutanoate | |
| Other names
Phorbol dibutyrate; Phorbol 12,13-dibutanoate
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | PDBu |
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PubChem CID
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| UNII | |
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| Properties | |
| C28H40O8 | |
| Molar mass | 504.620 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
Phorbol 12,13-dibutyrate (PDBu) is a phorbol ester which is one of the constituents of croton oil. As an activator of protein kinase C, it is a weak tumor promoter compared to 12-O-tetradecanoylphorbol-13-acetate.[1]
Tritiated PDBu has been used to study the way that phorbol esters bind to the protein kinase C receptor.[2]
Metabolism
The enzyme phorbol-diester hydrolase originally characterised from murine liver hydrolyses PDBu to remove one specific butyrate ester, giving phorbol 13-butanoate and butyric acid. It also acts on 12-O-tetradecanoylphorbol-13-acetate.[3]
- REDIRECT Template:Chemical reaction
Only phorbol diesters are tumor promoters, so this reaction inactivates them.[1][4]
References
- ↑ 1.0 1.1 "Phorbol ester receptors and the in vitro effects of tumor promoters". Annals of the New York Academy of Sciences 407 (1): 303–315. 1983. doi:10.1111/j.1749-6632.1983.tb47836.x. PMID 6309054. Bibcode: 1983NYASA.407..303B.
- ↑ Sharkey, Nancy A.; Blumberg, Peter M. (1 January 1985). "Highly Lipophilic Phorbol Esters as Inhibitors of Specific [3HPhorbol 12,13-Dibutyrate Binding"]. Cancer Research 45 (1): 19–24. https://aacrjournals.org/cancerres/article-pdf/45/1/19/2420255/cr0450010019.pdf.
- ↑ "Isolation and characterization of an ester hydrolase active on phorbol diesters from murine liver". J. Biol. Chem. 256 (23): 12529–34. 1981. doi:10.1016/S0021-9258(18)43307-8. PMID 6946062.
- ↑ De Barros, Cândida R. M.; Ferreira, Luis M. M.; Nunes, Fernando M. et al. (2011). "The potential of white-rot fungi to degrade phorbol esters of Jatropha curcas L. Seed cake". Engineering in Life Sciences 11: 107–110. doi:10.1002/elsc.201000040. https://research.wur.nl/en/publications/the-potential-of-white-rot-fungi-to-degrade-phorbol-esters-of-jat.
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