Synthesis, structure, and in vitro antiproliferative activity of cyclic hypervalent organobismuth(III) chlorides and their triphenylgermylpropionate derivatives

Xiao Wen Zhang, Jun Xia, Hui Wen Yan, Sheng Lian Luo, Shuang Feng Yin*, Chak Tong AU, Wai Yeung WONG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

Six compounds of cyclic hypervalent organobismuth(III) chlorides and triphenylgermylpropionates bearing a nitrogen or sulfur atom as intramolecular coordination atom have been synthesized and characterized. The results of single-crystal X-ray analysis reveal that the eight-membered tetrahydroazabismocine rings are highly flexible. The Bi-S or Bi-N bond lengths in the thiabismocine or azabismocine derivatives are dependent on how the substituted groups are acting on the Bi, S or N atom. The replacement of the chlorine atom in azabismocine and thiabismocine with the triphenylgermylpropionic group (Ph3GeCH2CH2COO{single bond}) leads to the lengthening of Bi-N and Bi-S bond. The substituents connected with the nitrogen atom also have an effect on the Bi-N bond length of azabismocine. For example, a cyclohexyl group has electron-donating ability higher than a phenyl group; the replacement of the former by the latter would lead to the decline of Bi-N bond length and increase of CAr-Bi-CAr angle in the eight-membered ring. The in vitro antiproliferative activities of the fabricated materials were compared on gastric carcinoma cells by means of the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide (MTT) method. It was found that the compounds show antiproliferative activity on gastric carcinoma cells (MGC-803) much higher than that of cisplatin. Moreover, there is enhancement of antiproliferative activity when the chlorine atom of the bismocine compounds is replaced by the triphenylgermylpropionic group, giving a low IC50 value of 0.7 μM for thiabismocine triphenylgermylpropionate.

Original languageEnglish
Pages (from-to)3019-3026
Number of pages8
JournalJournal of Organometallic Chemistry
Volume694
Issue number18
DOIs
Publication statusPublished - 15 Aug 2009

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

User-Defined Keywords

  • Antiproliferative activity
  • Bismuth
  • Germanium
  • Hypervalent

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