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Synthesis of N-Tetradecyl-1,10-phenathrolinium-Based New Salts for Biological Applications.
Bioinorganic Chemistry and Applications ( IF 4.7 ) Pub Date : 2018-07-17 , DOI: 10.1155/2018/8097483
Atakilt Abebe 1 , Minaleshewa Atlabachew 1 , Misganaw Liyew 2 , Elsabet Ferede 2
Affiliation  

New organic salts were synthesized by quaternizing 1,10-phenanthroline using 1-bromotetradecane. The first step yielded an organic salt of formula [C26H37N2]Br. Anion exchange reaction using Li[(CF3SO2)2N] resulted in a more stable salt of formula [C26H37N2][(CF3SO2)2N]. The organic salts were investigated by spectrometry (1H, 13C, 19F NMR, X-ray photoelectron spectroscopy (XPS), UV-Vis, and matrix-assisted laser desorption/ionization mass spectroscopy (MALDI MS), CHNSBr elemental analysis, and thermal analysis (TGA and DSC). The thermal characterization showed the melting and decomposition points of [C26H37N2][(CF3SO2)2N] to be 48°C and 290°C, respectively, which indicates it is an ionic liquid with large liquidus range. The biological activities of the salts were investigated against two Gram-positive (Staphylococcus aureus and Streptococcus pyogenes) and two Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria, and they are found to be active against all of them. They were compared with [Cu(1,10-phenanthroline)2Cl]Cl. They are found more active against the Gram-negative bacteria. The salts demonstrated minimum inhibitory concentration as low as 50 µg/L. These results suggest the synthesized salts can be considered as a better alternative to certain transition metal complex drugs. This minimizes the concern of introducing metal ions into the organism.

中文翻译:

合成用于生物应用的N-十四烷基1,10-菲咯啉基新盐。

通过使用1-溴十四烷季铵化1,10-菲咯啉来合成新的有机盐。第一步得到式[C 26 H 37 N 2 ] Br的有机盐。使用Li [(CF 3 SO 22 N]进行阴离子交换反应得到了更稳定的式[C 26 H 37 N 2 ] [(CF 3 SO 22 N]盐。通过分光光度法(1 H,13 C,19F NMR,X射线光电子能谱(XPS),UV-Vis和基质辅助激光解吸/电离质谱(MALDI MS),CHNSBr元素分析和热分析(TGA和DSC)。热特性表明,[C 26 H 37 N 2 ] [(CF 3 SO 22 N]的熔点和分解点分别为48℃和290℃,这表明它是具有大液相线的离子液体。范围。研究了盐对两种革兰氏阳性(金黄色葡萄球菌化脓性链球菌)和两种革兰氏阴性(大肠杆菌肺炎克雷伯菌)的生物学活性。)细菌,发现它们对所有细菌都有活性。将它们与[Cu(1,10-菲咯啉)2 Cl] Cl进行比较。发现它们对革兰氏阴性细菌更具活性。盐显示出最低抑制浓度低至50  µg / L。这些结果表明,合成盐可以被认为是某些过渡金属络合物药物的更好替代品。这最小化了将金属离子引入生物体的担忧。
更新日期:2018-07-17
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