Anticancer activity of 5-benzylidene-2-phenylimino-1, 3-thiazolidin-4-one (BPT) analogs

S. Wu, W. Guo, F. Teraishi, J. Pang, K. Kaluarachchi, L. Zhang, J. Davis, F. Dong, B. Yan, B. Fang

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

We recently identified two compounds of 5-benzylidene-2-phenylimino-1,3-thiazolidin-4-one (BPT) analog,5-(4-methylbenzylidene)-2-phenylamino-1,3-thiazolidin-4-one (MMPT) and 5-(2,4-dihydroxybenzylidene)-2-phenylimino1, 3-thiazolidin-4-one (DBPT), that can effectively induce apoptosis in cancer cells but not in normal cells, independently of P-glycoprotein status. To further investigate the antitumor activity of BPT analogs, we obtained 18 commercially available analogs of BPT and synthesized 7 analogs in our lab, and analyzed their antitumor activity in various cancer cells, including paclitaxel- and vinorelbine-sensitive and -resistant human lung cancer cells. Two of the compounds were more potent than MMPT or DBPT in induction of apoptosis in certain cancer cell lines and remained tumor selective. Seven compounds did not induce any cytotoxic effects in any of the cell lines tested at the highest concentration tested (31 μM). The other compounds induced cytotoxic effects in some cancer cells but not in others or were less potent than MMPT and DBPT. Cell uptake studies showed that analogs that effectively induced cell killing in paclitaxel- and vinorelbine-resistant cells could be taken up easily by those cells despite their high levels of P-glycoprotein expression. These data further demonstrate that thiazolidinone analogs are not P-glycoprotein substrates and could be useful for treatment of P-glycoprotein overexpressing refractory cancers.

Original languageEnglish
Pages (from-to)597-605
Number of pages9
JournalMedicinal Chemistry
Volume2
Issue number6
DOIs
Publication statusPublished - Nov 2006
Externally publishedYes

Keywords

  • 5-Benzylidene-2-Phenylimino-4-Thiazolidin-4-one (BPT) analog
  • Antitumor activity
  • Apoptosis
  • Chemical core structure
  • Cytotoxic effects
  • LC-MS
  • Multidrug-resistance
  • P-glycoprotein

ASJC Scopus subject areas

  • Drug Discovery

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  • Cite this

    Wu, S., Guo, W., Teraishi, F., Pang, J., Kaluarachchi, K., Zhang, L., Davis, J., Dong, F., Yan, B., & Fang, B. (2006). Anticancer activity of 5-benzylidene-2-phenylimino-1, 3-thiazolidin-4-one (BPT) analogs. Medicinal Chemistry, 2(6), 597-605. https://doi.org/10.2174/1573406410602060597