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Issue 11, 2016
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Phosphorus–nitrogen compounds. Part 36. Syntheses, Langmuir–Blodgett thin films and biological activities of spiro-bino-spiro trimeric phosphazenes

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Abstract

The condensation reactions of hexachlorocyclotriphosphazene (N3P3Cl6, trimer) with the symmetric N2N2 or N2O2 donor type tetradentate bulky ligands (1–4) gave partly substituted spiro-bino-spiro (sbs) (5–8) trimeric phosphazenes. Compounds 5–8 reacted with pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) to give octapyrrolidino- (9–12), morpholino- (13–16) and DASD-substituted cyclotriphosphazenes (17–20). The structures of the phosphazenes have been elucidated using FTIR, MS, 1H, 13C{1H} and 31P{1H} NMR, and HSQC spectral data. The molecular and solid-state structures of 5, 6 and 12 were verified by single crystal X-ray diffraction techniques. On the other hand, the ultrathin and highly ordered Langmuir–Blodgett (LB) films of compounds 6, 7, 9 and 12 were also fabricated. The structural characterization of the LB films was made using p-polarized grazing angle (GAIR) and horizontal attenuated total reflectance (HATR) techniques. All the novel phosphazene derivatives were evaluated for antibacterial activities against Gram-positive (G+) and Gram-negative (G−) bacteria and for antifungal activities against yeast strains. In addition, the cytotoxic effects of compounds 9, 13, 15, 16, 19 and 20 were investigated against L929 fibroblast and MDA-MB-231 breast cancer cells. The most active one among these compounds was compound 9 at 6.25 μg mL−1 concentration. The interactions between compounds 5–20 and pBR322 plasmid DNA were determined by agarose gel electrophoresis.

Graphical abstract: Phosphorus–nitrogen compounds. Part 36. Syntheses, Langmuir–Blodgett thin films and biological activities of spiro-bino-spiro trimeric phosphazenes

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Publication details

The article was received on 01 Jul 2016, accepted on 15 Sep 2016 and first published on 15 Sep 2016


Article type: Paper
DOI: 10.1039/C6NJ02052F
Citation: New J. Chem., 2016,40, 9609-9626
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    Phosphorus–nitrogen compounds. Part 36. Syntheses, Langmuir–Blodgett thin films and biological activities of spiro-bino-spiro trimeric phosphazenes

    N. Asmafiliz, Z. Kılıç, M. Civan, O. Avcı, L. Yasemin Gönder (<em xmlns="http://www.rsc.org/schema/rscart38">née</em> Koç), L. Açık, B. Aydın, M. Türk and T. Hökelek, New J. Chem., 2016, 40, 9609
    DOI: 10.1039/C6NJ02052F

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