Phorbol 12,13-dibutyrate

Phorbol 12,13-dibutyrate
Names
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
Identifiers
3D model (JSmol)
Abbreviations PDBu
ChEBI
ChemSpider
ECHA InfoCard 100.164.231 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,33-34H,7-10,13-14H2,1-6H3/t16-,18+,19-,22-,24-,26-,27-,28-/m1/s1 checkY
    Key: BQJRUJTZSGYBEZ-YVQNUNKESA-N checkY
  • CCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)CCC)O)C
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).

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.

Tritiated PDBu has been used to study the way that phorbol esters bind to the protein kinase C receptor.

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.

2D representation of the chemical structure of Phorbol 12,13-dibutyrate.
PDBu
 
H2O
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of Q27102560.
phorbol 13-butanoate
+
 
2D representation of the chemical structure of butyric acid.
butyric acid

Only phorbol diesters are tumor promoters, so this reaction inactivates them.

References

  1. 1 2 Blumberg PM, Delclos KB, Dunn JA, Jaken S, Leach KL, Yeh E (1983). "Phorbol ester receptors and the in vitro effects of tumor promoters". Annals of the New York Academy of Sciences. 407 (1): 303–315. Bibcode:1983NYASA.407..303B. doi:10.1111/j.1749-6632.1983.tb47836.x. PMID 6309054. S2CID 20089027.
  2. ↑ Sharkey, Nancy A.; Blumberg, Peter M. (1 January 1985). "Highly Lipophilic Phorbol Esters as Inhibitors of Specific [3H]Phorbol 12,13-Dibutyrate Binding" (PDF). Cancer Research. 45 (1): 19–24.
  3. ↑ Shoyab M, Warren TC, Todaro GJ (1981). "Isolation and characterization of an ester hydrolase active on phorbol diesters from murine liver". J. Biol. Chem. 256 (23): 12529–34. doi:10.1016/S0021-9258(18)43307-8. PMID 6946062.
  4. ↑ 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.