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    Synthesis and photophysical characterization of heterocyclic dihydrotetracenes and their utility in the fluorescence imaging of HeLa cells

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    Date
    2018
    Author
    Banerjee, S.
    Phadte, A.A.
    Chattopadhyay, A.
    Fernandes, J.R.D.
    Savardekar, A.V.
    Banerjee, A.
    Singh, K.S.
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    Abstract
    Aza- and oxa-dihydrotetracenes were prepared in one step from 1,4-dicyanodibenzodioxins in good yields. These molecules represent the first examples of heterocyclic dihydrotetracenes with push-pull character. Aza-dihydrotetracene 18H showed a strong red-shifted absorbance maxima at 472-nm, nearly equal in intensity to the parent band at 260-nm, in polar DMSO medium. The fluorescence emission spectrum of aza-dihydrotetracene 18H had an emission maximum at 525-nm with a broad band stretched out as far as 650-nm. The fluorescence emission quantum yield was almost as strong as the known fluorescent standard 1,3-diphenylisobenzofuran. The aza-dihydrotetracenes exhibited in vitro cytotoxicity against the HeLa cell line and were non-toxic against the normal HaCaT cell line. The fluorescence emerging from HeLa cells incubated with aza-dihydrotetracene 18H was very strong and helped detect the cells microscopically using appropriate filters. A useful future application of the compound could be as a fluorescence based dye in cellular microscopy.
    URI
    https://doi.org/10.1016/J.TETLET.2018.09.013
    http://drs.nio.org/drs/handle/2264/7968
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