Synthesis, structure, and in vitro antiproliferative activity of cyclic hypervalent organobismuth(III) chlorides and their triphenylgermylpropionate derivatives |
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Authors: | Xiao-Wen Zhang Jun Xia Sheng-Lian Luo Chak-Tong Au Wai-Yeung Wong |
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Affiliation: | a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, PR China b Key Laboratory of Pollution Control and Resource Use of Hunan Province, University of South China, Hengyang 421001, PR China c Cell Biology of Bioscience and Technology Academy, Central South University, Changsha 410013, PR China d Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, PR China e Department of Chemistry and Centre for Advanced Luminescence Materials, Hong Kong Baptist University, Kowloon Tong, Hong Kong, PR China |
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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) 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. |
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Keywords: | Bismuth Germanium Hypervalent Antiproliferative activity |
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