Phosphorus–nitrogen compounds part 33: in vitro cytotoxic and antimicrobial activities, DNA interactions, syntheses, and structural investigations of new mono(4-nitrobenzyl)spirocyclotriphosphazenes
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- 作者：Aytuğ Okumuş ; Hüseyin Akbaş ; Zeynel Kılıç…
- 关键词：Spirocyclotriphosphazenes ; Spectroscopy ; Crystal structure ; Cytotoxicity ; Breast and HeLa cancer cell lines ; DNA interactions
- 刊名：Research on Chemical Intermediates
- 出版年：2016
- 出版时间：May 2016
- 年：2016
- 卷：42
- 期：5
- 页码：4221-4251
- 全文大小：1,701 KB
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Hüseyin Akbaş (2)
Zeynel Kılıç (1)
L. Yasemin Koç (3)
Leyla Açık (4)
Betül Aydın (4)
Mustafa Türk (5)
Tuncer Hökelek (6)
Hakan Dal (7)
1. Department of Chemistry, Ankara University, 06100, Ankara, Turkey
2. Department of Chemistry, Gaziosmanpaşa University, 60150, Tokat, Turkey
3. The Turkish Sugar Authority, 06510, Ankara, Turkey
4. Department of Biology, Gazi University, 06500, Ankara, Turkey
5. Department of Bioengineering, Kırıkkale University, Kirikkale, Turkey
6. Department of Physics, Hacettepe University, 06800, Ankara, Turkey
7. Department of Chemistry, Anadolu University, 26470, Eskisehir, Turkey - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Catalysis
Physical Chemistry
Inorganic Chemistry - 出版者：Springer Netherlands
- ISSN：1568-5675
文摘
The condensation reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with N-alkyl-N′-mono(4-nitrobenzyl)diamines (1–3), NO2PhCH2NH(CH2) n NHR1 (R1 = CH3 or C2H5), led to the formation of the mono(4-nitrobenzyl)spirocyclotriphosphazenes (4–6). The tetra-pyrrolidino (4a–6a), piperidino (4b–6b), and 1,4-dioxa-8-azaspiro[4,5]decaphosphazenes (4c–6c) were prepared from(for) the reactions of partly substituted compounds (4, 5, and 6) with excess pyrrolidine, piperidine, and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The partly substituted geminal (4d and 5d) and cis-morpholino (6d) phosphazenes were isolated from the reactions of excess morpholine in boiling THF and o-xylene, but the expected fully substituted compounds were not obtained. The structures of all the phosphazene derivatives were determined by elemental analyses, MS, FTIR, 1H, 13C{1H}, 31P{1H} NMR, HSQC, and HMBC techniques. The crystal structures of 4, 6, 4a, and 5a were verified by X-ray diffraction analysis. In addition, in vitro cytotoxic activities of fully substituted phosphazenes (4a–6c) against HeLa cervical cancer cell lines (ATCC CCL-2) and the compounds 4a and 4c against breast cancer cell lines (MDA-MB-231) and L929 fibroblast cells were evaluated, respectively. Apoptosis effect was determined by MDA-MB-231 cancer cell lines and fibroblast cells. The MIC values of the compounds were in the ranges of 9.8–19.5 µM. The compounds 6, 5a, 6a, 5b, and 6d have greater MIC activity against bacterial and yeast strain. The investigation of DNA binding with the phosphazenes was studied using plasmid DNA. The phosphazene derivatives inhibit the restriction endonuclease cleavage of plasmid DNA by BamHI and HindIII enzymes. BamHI and HindIII digestion results demonstrate that the compounds bind with G/G and A/A nucleotides.