Novel oleanolic vinyl boronates: synthesis and antitumor activity

Vânia M. Moreira, Jorge A.R. Salvador, Sérgio Simões, Federica Destro, Riccardo Gavioli

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A series of novel oleanane-type pentacyclic triterpenoids bearing a boronate ester moiety at C3 have been synthesized by palladium-catalyzed cross-coupling of bis(pinacolato)diboron with vinyl triflates, in the presence of base, and these compounds were fully characterized by 1D and 2D NMR techniques. Evaluation of their antiproliferative effects on a panel of hematological-based and solid tumor cell lines identified three active oleanolic vinyl boronates that inhibited the growth of leukemia (Jurkat, K562), Burkitt's lymphoma (Jijoye), cervix (Hela), colon (SW480), and ovary (SKOV-3) cancer cells without concomitant inhibition of non-tumoral human fibroblasts. Their mechanisms of action were investigated on the leukemia Jurkat cell line. The results show that the incorporation of boron in the oleanolic acid core combined with the presence of amide bonds afforded compounds with desirable biological effects such as apoptosis induction and inhibition of proteasomal activity on tumor cells, which makes them potential templates for further development in the anticancer drug setting.

LanguageEnglish
Pages46-56
Number of pages11
JournalEuropean Journal of Medicinal Chemistry
Volume63
DOIs
Publication statusPublished - 31 May 2013

Fingerprint

Leukemia
Cells
Oleanolic Acid
Boron
Jurkat Cells
Burkitt Lymphoma
Palladium
Tumor Cell Line
Amides
Cervix Uteri
Tumors
Ovary
Neoplasms
Colon
Esters
Bearings (structural)
Fibroblasts
Apoptosis
Cell Line
Growth

Keywords

  • triterpenoids
  • oleanolic
  • boronates
  • apoptosis
  • proteasome

Cite this

Moreira, Vânia M. ; Salvador, Jorge A.R. ; Simões, Sérgio ; Destro, Federica ; Gavioli, Riccardo. / Novel oleanolic vinyl boronates : synthesis and antitumor activity. In: European Journal of Medicinal Chemistry. 2013 ; Vol. 63. pp. 46-56.
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Novel oleanolic vinyl boronates : synthesis and antitumor activity. / Moreira, Vânia M.; Salvador, Jorge A.R.; Simões, Sérgio; Destro, Federica; Gavioli, Riccardo.

In: European Journal of Medicinal Chemistry, Vol. 63, 31.05.2013, p. 46-56.

Research output: Contribution to journalArticle

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AU - Moreira, Vânia M.

AU - Salvador, Jorge A.R.

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