Phosphorus-nitrogen compounds. Part 58. Syntheses, structural characterizations and biological activities of 4-fluorobenzyl-spiro(N/O)cyclotriphosphazene derivatives.

The starting compound, tetrachloro-4-fluorobenzyl-spiro(N/O)cyclotriphosphazene (2), was synthesized from the substitution reaction of hexachlorocyclotriphosphazatriene (N3P3Cl6; trimer; HCCP) with sodium 3-(4-fluorobenzylamino)-1-propanoxide (1). Reactions of spiro (2) with excess 1-(2-aminoethyl)-piperidine, 4-(2-aminoethyl)-morpholine, 1-(2-hydroxyethyl)piperidine and 4-(2-aminoethyl)morpholine yielded the fully substituted cyclotriphosphazene derivatives (2a-2d), respectively. Elemental analysis, mass spectrometry (ESI-MS), FTIR, 1H-, 13C- and 31P-NMR data confirmed the structure of the new cyclotriphosphazenes (2a-2d); and the crystal structure of 2 was also identified by X-ray crystallography. The quantum mechanical DFT calculations of 2 were performed to estimate the geometry optimization, total energy, orientation of frontier molecular orbitals (HOMOs and LUMOs), and chemical parameters. In addition, antibacterial and antifungal activities of the fully substituted 4-fluorobenzyl-spiro(N/O)cyclotriphosphazenes (2a-2d) were investigated against G(+) and G(-) bacteria and fungi. Using agarose gel electrophoresis, the DNA cleavage activities of these phosphazenes on double-stranded plasmid DNA were evaluated. To evaluate the abilities of compounds 2a-2d to inhibit cell proliferation in different concentrations, the antiproliferative and antimigrative activities against prostate adenocarcinoma (PC3), breast cancer (MCF7) and colon cancer (HT29) cell lines were studied in vitro; and the compound 2c was determined to be the most efficient against the three cancer cells.Communicated by Ramaswamy H. Sarma.

Morphometric analysis of sphenopalatine foramen on computed tomography images with clinical significance.

PURPOSE: This study aimed to investigate the effect of anatomical variations in the sphenopalatine foramen and the lateral nasal wall on sphenopalatine foramen-related morphometric measurements. METHODS: Paranasal sinus multidetector computed tomography records of 153 patients were evaluated. Morphometric measurements were made between the fixed bony landmarks and the sphenopalatine foramen. Number, shape, localization variations of the sphenopalatine foramen, concha bullosa, and septum deviation were noted and the results were compared with respect to sex, age, and laterality. RESULTS: No significant difference was detected with respect to laterality, whereas most of the measured distances were higher in males than females. There was a significant difference between the obtained morphometric data according to age groups. In our study, 91.2% single, 7.8% double, and 1% triple sphenopalatine foramen were detected and the most common irregularly shaped (37.3%). The location of sphenopalatine foramen was reported as the most common type II. Septum deviation types have no potential influence on the location of the foramen, but most of the measured parameters were found to be significantly smaller in the presence of concha bullosa, whereas the angle was found to be higher. CONCLUSION: This study revealed a significant relationship between the morphometric measurements of the sphenopalatine foramen and concha bullosa, while septum deviation types did not affect these results. For a safer and more effective surgery with prevention of iatrogenic complications, a surgeon should be aware of this correlation, especially in endoscopic transnasal approaches.