Abstract：
:2-azetidinones and 2H-azirines show antibacterial and cytotoxic activities, however the biological properties of molecules containing both 2H-azirine and 2-azetidinone functions in the same structure had never been evaluated before. In the present study, two 2H-azirine-2-azetidinones (1 and 2) and three 2H-azirines (3-5) were synthesized from 2-formyl-3-phenyl-2H-azirine-N-arylimines with diphenylketene. The compounds were assayed for antibacterial and cytotoxic activities. None of them showed antibacterial activity on the tested strains, but both 2H-azirine-2-azetidinones showed cytotoxicity against four tumor cell lines (HL-60, leukemia; HCT-8, colon cancer; MDA-MB-435, melanoma; and SF-295, CNS). The IC(50) values of 1 ranged from 1.1 to 10.5 microM and from 3.8 to 26.6 microM for 2. The mechanism of cell growth inhibition of 1 and 2 towards HL-60 cell line was also investigated. Membrane damage, cell viability, DNA synthesis inhibition and morphological changes were evaluated. The preliminary findings suggested that 1 and 2 induce apoptosis.
journal_name
Chem Biol Interactjournal_title
Chemico-biological interactionsauthors
Maia DP,Wilke DV,Mafezoli J,da Silva Júnior JN,de Moraes MO,Pessoa C,Costa-Lotufo LVdoi
10.1016/j.cbi.2009.02.015subject
Has Abstractpub_date
2009-07-15 00:00:00pages
220-5issue
2eissn
0009-2797issn
1872-7786pii
S0009-2797(09)00086-6journal_volume
180pub_type
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