Synthesis and characterization of per-substituted spermine-bridged cyclophosphazene derivatives: the first example of syn/anti conformational polymorphism in a bridged cyclophosphazene

Çiftçi, Gönül Yenilmez

doi:10.1016/j.inoche.2004.09.019

Cited by 10 publications

(1 citation statement)

References 16 publications

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“…The asymmetric unit of all compounds includes only one molecule and the cyclotriphosphazene rings are fully substituted with octamethyl-, ethyl-, propyl-, butyl-, and benzylparabens, as shown in ball−stick represantations in Figures 3 and 4 14)°, and are somewhat larger than those of the above-mentioned N−P− N angles. Analysis of previously reported crystallographic studies on spermine-bridged cyclophosphazene derivatives showed that a free rotation around single C−C bound in the flexible alkyl-chain could lead to the two conformations, which is identified as syn (CSD refcode: COPTUW01, 42 PAJVUS, 43 GUZPOG, 44 GUZPIA 44 or anti (CSD refcode: COPTUW, 41 BADJEW, 45 BADJIA, 45 CEGNEI, 46 CEGNIM, 46 GIFBAA 34 ) conformations of the cyclophosphazene moiety with respect to each other. In all compounds, two cyclotriphosphazenes stand in anti-conformation to each other, possibly under the influence of crowded paraben groups.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Electrophoresis and Biosensor-Based DNA Interaction Analysis of the First Paraben Derivatives of Spermine-Bridged Cyclotriphosphazenes

et al. 2020

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Cancer is the uncontrolled growth of abnormal cells via malignant cell division and rapid DNA replication. While DNA damaging molecules can cause cancer, their role as anticancer drugs are very significant. For this purpose, the novel series of paraben substituted spermine bridged(dispirobino) cyclotriphosphazene compounds 2−6 were synthesized for the first time, and their structures were characterized by various spectroscopic techniques. The solid-state structures and geometries of compounds 2−6 were determined using single-crystal X-ray structural analysis. In addition, it was confirmed by TGA that all compounds 1−6 showed high thermal stability. Two methods were used in order to investigate DNA interaction properties of the targeted molecules. While biosensor-based screening test that measures DNA hybridization efficiency on a biochip surface, the agarose gel electrophoresis method examines the effect of compounds on plasmid DNA structure. The results collected from the automated biosensor device and agarose gel electrophoresis have indicated that compounds 1, 5, and 6 showed higher DNA damage than the compounds 2−4. According to the biosensor results, compounds 1, 5, and 6 showed 85%, 69%, and 77% activity, respectively.

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