Bis(2-furanylmethyl)monospiro(N/N)cyclotriphosphazenes: synthesis, structural characterization, antiproliferative, and antimigratory activity studies

IF 1.6 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2023-12-02 DOI:10.1080/10426507.2023.2242995

Hüseyin Akbaş , Ayşegül Şenocak , Zeynel Kılıç , Seçil Erden Tayhan , Sema Bilgin , Aslı Yıldırım Kocaman , Tuncer Hökelek

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Abstract

In this study, the condensation reaction of hexachlorocyclotriphosphazene, N₃P₃Cl₆ (HCCP) with N ¹,N³-bis(furan-2-ylmethyl)-1,3-diamino-propane (1) yielded tetrachlorobis(2-furanyl-methyl)monospiro(N/N)cyclotriphosphazene (2). Fully substituted tetraaminobis(2-furanylmethyl)-spiro(N/N)cyclotriphosphazenes (2a and 2b) were obtained by Cl replacement reactions with excess pyrrolidine and piperidine, respectively, using dry THF under reflux of 2. The structures of the phosphazenes were confirmed by data obtained by elemental analysis, FT-IR, ESI-MS, ¹H, ¹³C, and ³¹P NMR. Moreover, the molecular structure of 2b was elucidated by X-ray crystallography. The antiproliferative effects of phosphazenes (2, 2a, and 2b) on prostate (PC-3) and colon cancer (HT-29) cell lines were determined by cell viability analysis using MTT assay. Antimigratory effects were also investigated by scratch analysis. In addition, the effects of compounds against genes involved in apoptosis and cell migration were evaluated by gene expression analysis. As a result, it was found that compound 2a was more effective than compound 2b in both prostate and colon cancer cell lines.

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双（2-呋喃基甲基）单螺（N/N）环三磷腈：合成、结构表征、抗增殖和抗迁移活性研究

在本研究中，六氯环三磷腈N3P3Cl6 （HCCP）与N 1，N3-二（呋喃-2-甲基）-1,3-二氨基丙烷(1)缩合反应得到四氯（2-呋喃-甲基）单螺（N/N）环三磷腈(2)。在2回流条件下，用干四氢呋喃与过量的吡咯烷和哌啶分别用Cl取代反应得到全取代的四氨基（2-呋喃-甲基）-螺（N/N）环三磷腈（2a和2b）。通过元素分析、FT-IR、ESI-MS、1H、13C和31P核磁共振等手段证实了磷腈的结构。利用x射线晶体学对其分子结构进行了分析。MTT法测定磷酸腈（2、2a、2b）对前列腺癌（PC-3）和结肠癌（HT-29）细胞株的抗增殖作用。通过划痕分析研究了其抗迁移作用。此外，通过基因表达分析评估化合物对参与细胞凋亡和细胞迁移的基因的影响。结果发现，化合物2a在前列腺和结肠癌细胞系中都比化合物2b更有效。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.

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