Synthesis and biological evaluations of cytotoxic and antiangiogenic triterpenoids-jacaranone conjugates

Hua Sun, Partick Y. K. Yue, Shao Rong Wang, Lihong Huo, Ying Zhao, Songbo Xie, Jens Vindahl Kringelum, Ole Lund, Olivier Taboureau, Jun Zhou, Ricky N. S. Wong, Wei Shuo Fang

    Research output: Contribution to journalJournal articleResearchpeer-review


    Background: The development of antiangiogenic agents arises as a more effective and selective therapeutic approach for the treatment of cancer. In addition to reduced acute toxicity, the efficacy of chemotherapy could be improved when administered in combination specific antiangiogenic with cytotoxic agents. The conjugation or hybridization of bifunctional molecules is one of the alternative rational design strategies for co-administration of anticancer drugs. Objective and Methods: The goal of this work is to prepare the conjugates of an antiangiogenic triterpene, 3-oxo oleanolic acid, and structurally related triterpenoids with a cytotoxic semibenzoquinone, jacaranone. The cytotoxic, antiproliferative and antiangiogenic activities of segments and conjugates were determined. The possible targets of conjugates 6a-6h were predicted using Similarity Ensemble Approach (SEA). Results: The results showed that these conjugates are more potent in both cytotoxic and antiangiogenic assays than their corresponding parent molecules, and are also selectively more active against melanoma cells B16 and metastatic B16BL6 than the two other cancer cell lines (A549 and MCF-7) tested. The predicted antiangiogenesis related targets could involve glycogen phosphorylase, neuraminidase, interferon gamma, and tubulin beta chain. Conclusion: The bifunctional conjugates could be useful as dual acting antitumor/antigiogenic agents.
    Original languageEnglish
    JournalMedicinal Chemistry
    Issue number8
    Pages (from-to)775-785
    Number of pages11
    Publication statusPublished - 2016


    • Antiangiogenesis
    • Antitumor agent
    • Conjugation
    • Jacaranone
    • Oleanolic acid


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