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用于生物应用的基于 - 十四烷基 - 1,10 - 菲咯啉鎓的新型盐的合成。

Synthesis of -Tetradecyl-1,10-phenathrolinium-Based New Salts for Biological Applications.

作者信息

Abebe Atakilt, Atlabachew Minaleshewa, Liyew Misganaw, Ferede Elsabet

机构信息

Chemistry Department, Science College, Bahir Dar University, Bahir Dar, Ethiopia.

Biology Department, Science College, Microbiology Research Laboratory, Bahir Dar University, Bahir Dar, Ethiopia.

出版信息

Bioinorg Chem Appl. 2018 Jul 17;2018:8097483. doi: 10.1155/2018/8097483. eCollection 2018.

DOI:10.1155/2018/8097483
PMID:30116259
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6079542/
Abstract

New organic salts were synthesized by quaternizing 1,10-phenanthroline using 1-bromotetradecane. The first step yielded an organic salt of formula [CHN]Br. Anion exchange reaction using Li[(CFSO)N] resulted in a more stable salt of formula [CHN][(CFSO)N]. The organic salts were investigated by spectrometry (H, C, F 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 [CHN][(CFSO)N] 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 ( and ) and two Gram-negative ( and ) bacteria, and they are found to be active against all of them. They were compared with [Cu(1,10-phenanthroline)Cl]Cl. They are found more active against the Gram-negative bacteria. The salts demonstrated minimum inhibitory concentration as low as 50 g/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.

摘要

通过用1-溴十四烷将1,10-菲咯啉季铵化合成了新型有机盐。第一步得到了化学式为[CHN]Br的有机盐。使用Li[(CFSO)N]进行阴离子交换反应,得到了更稳定的化学式为[CHN][(CFSO)N]的盐。通过光谱法(H、C、F NMR、X射线光电子能谱(XPS)、紫外可见光谱和基质辅助激光解吸/电离质谱(MALDI MS))、CHNSBr元素分析以及热分析(热重分析和差示扫描量热法)对有机盐进行了研究。热表征表明,[CHN][(CFSO)N]的熔点和分解点分别为48°C和290°C,这表明它是一种具有较大液相范围的离子液体。研究了这些盐对两种革兰氏阳性菌(和)和两种革兰氏阴性菌(和)的生物活性,发现它们对所有这些细菌都有活性。将它们与[Cu(1,10-菲咯啉)Cl]Cl进行了比较。发现它们对革兰氏阴性菌更具活性。这些盐的最低抑菌浓度低至50 g/L。这些结果表明,合成的盐可被视为某些过渡金属络合物药物的更好替代品。这最大限度地减少了将金属离子引入生物体的担忧。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/f63ae8a519ca/BCA2018-8097483.004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/ddbcb5f4f173/BCA2018-8097483.sch.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/46e4401a7db8/BCA2018-8097483.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/1ef442f3750e/BCA2018-8097483.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/70971943b3bf/BCA2018-8097483.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/f63ae8a519ca/BCA2018-8097483.004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/ddbcb5f4f173/BCA2018-8097483.sch.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/46e4401a7db8/BCA2018-8097483.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/1ef442f3750e/BCA2018-8097483.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/70971943b3bf/BCA2018-8097483.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f83/6079542/f63ae8a519ca/BCA2018-8097483.004.jpg

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