Synthesis and tumor-promoting activities of 12-Epi-phorbol-12,13-dibutyrate

Kazuhiro Irie, Akifumi Nakahara, Yasuyuki Ikawa, Minoru Tanaka, Yu Nakagavva, Yoshimasa Nakamura, Hajime Ohigashi, Paul A. Wender

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)


12-Epi-phorbol-12,13-dibutyrate (1), the C12-epimer of the most frequently used phorbol ester probe, phorbol-12,13-dibutyrate (PDBu), has been synthesized from phorbol in 9 steps in order to investigate the structural requirements for tumor-promoting activity. Compound 1 showed about 100-fold weaker in vitro biological activities related to in vivo tumor promotion, Epstein-Barr virus early antigen (EBV-EA)-inducing ability, superoxide (O2) generation-inducing ability, and binding to the protein kinase C (PKC) regulatory domain surrogate peptides. The results indicated that the β-stereochemistry at position 12 of the phorbol skeleton is important for optimal activity. Binding selectivity to each PKC C1 domain of 1 was almost equal to that of PDBu.

Original languageEnglish
Pages (from-to)2429-2436
Number of pages8
JournalBioscience, Biotechnology and Biochemistry
Issue number11
Publication statusPublished - 2000
Externally publishedYes


  • 12-epi-phorbol-12,13-dibutyrate
  • Epstein-Barr virus
  • Phorbol ester
  • Protein kinase C
  • Tumor promoter

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry


Dive into the research topics of 'Synthesis and tumor-promoting activities of 12-Epi-phorbol-12,13-dibutyrate'. Together they form a unique fingerprint.

Cite this