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Synthesis, cytotoxicity, and promising anticancer potential of novel β-amino- and β-iminophosphonates

Vanya Koleva, Irina Yotova, Asya Dragoeva, Dobromir Enchev.

New series of β-amino- and β-iminophosphonates were produced via a nucleophilic addition reaction of benzyl amine and 2-aminopirydine to 1,2-alkadienephosphonates. Cytotoxicity and anticancer potential of newly synthetisized compounds were investigated. Triticum aestivum L. root growth inhibition test and Allium cepa L. assay were used to assess the cytotoxic potential of phosphonates. Anticancer activity on human fibrosarcoma cell line HT 1080 was assessed. The antiproliferative effect of compounds was determined by WST-1 test, and nuclear morphology changes in cancer cells stained with Giemsa were evaluated. After treatment with β-iminophosphonate (E,Z)(3-Methyl-2-(pyridin2-ylimino)butyl)diphenylphosphine oxide (4e) proliferation/viability of cancer cells was strongly inhibited and in 65.61% of the cells signs of early apoptosis were observed. The results reported here show once again phosphonates as versatile substrates in synthetic organic chemistry, especially as fruitful starting compounds for the achievement of molecular diversity. Among tested compounds β-iminophosphonate (E,Z)(3-Methyl-2-(pyridin-2-ylimino)butyl) diphenylphosphine oxide (4e) showed anticancer activity against human fibroblastoma cell line HT 1080.

Key words: β-aminophosphonates, β-iminophosphonates, cytotoxicity, anticancer potential, apoptosis

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