Synthesis and spectroscopic characterizations of hexakis[(1-(4′-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes: their in vitro cytotoxic activity, theoretical analysis and molecular docking studies

The hexachlorocyclotriphosphaze compound (N 3 P 3 Cl 6 , HCCP) was reacted with excess (E)-(1-(4′-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-ones (2-11) to produce hexakis[(1-(4-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes (CP 2-11). The structures of products (CP 2-11) w...

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Bibliographic Details
Published in:Journal of biomolecular structure & dynamics 2022-05, Vol.40 (7), p.3258-3272
Main Authors: Doğan, Hacer, Bahar, Mehmet Refik, Çalışkan, Eray, Tekin, Suat, Uslu, Harun, Akman, Feride, Koran, Kenan, Sandal, Süleyman, Görgülü, Ahmet Orhan
Format: Article
Language:English
Subjects:
cytotoxicity
molecular docking
MTT assay
spiro-phosphazene
structural characterizations
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Summary:The hexachlorocyclotriphosphaze compound (N 3 P 3 Cl 6 , HCCP) was reacted with excess (E)-(1-(4′-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-ones (2-11) to produce hexakis[(1-(4-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes (CP 2-11). The structures of products (CP 2-11) were confirmed using elemental analysis, FT-IR, MS spectral analysis as well as 31 P, 1 H and 13 C-APT NMR techniques and their thermal properties determined by TGA and DSC techniques. The HOMO-LUMO energy gap and chemical reactivity identifiers were calculated and HOMO and LUMO images were viewed. According to the calculations, all the chemical potential values of CP 2-11 are negative and it shown that the molecules are stable. The in vitro cytotoxic of CP 2-11 investigated and their activity potentials were evaluated by molecular docking studies with Autodock Vina softwares. CP 2-11 compounds were found to demonstrate cytotoxic activity against human cancer cell lines (A2780, LNCaP and PC-3). The CP 2-11 compounds reduced the cell viability against all cancer cell lines in the range 36%-90% especially. The results showed that these compounds are powerful candidate molecules for pharmaceutical applications. Synthesis, spectroscopic and thermal properties, in vitro cytotoxic properties, theoretical analysis and molecular docking studies of hexa substituted cyclotriphosphazenes CP 2-11 were investigated. Communicated by Ramaswamy H. Sarma
ISSN:0739-1102
1538-0254
DOI:10.1080/07391102.2020.1846621