Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex.
Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex.
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DOI：
10.1021/acs.cgd.0c00107
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发表时间：
2020-08-05
影响因子：
3.8
通讯作者：
Pan L
中科院分区：
文献类型：
--
作者：
Dubovoy V;Desai P;Hao Z;Cheng CY;Verma G;Wojtas L;Brinzari TV;Boyd JM;Ma S;Asefa T;Pan L
报道了包含1：2比例的氯己定（CHX）与N-环己基氨基磺酸酯（即，称为环己基氨基磺酸盐的人造甜味剂）。通过结合单晶X射线衍射（SC-XRD）、电喷雾电离质谱（ESI-MS）、1H核磁共振（NMR）光谱、相关光谱（COSY）和衰减全反射傅里叶变换红外光谱（ATR-FTIR），明确鉴定了化学结构。新材料：1）是迄今为止发现的仅有的几种含有重要氯己定抗微生物药物的报告结构之一; 2）在浓度低于15 μ g/mL时表现出广谱抗微生物活性; 3）为基本活性药物成分（API）提供了独特的递送方法。此外，用生物活性环己基氨基磺酸盐替代无活性的葡萄糖酸盐可能提供改善氯己定的味道特征的额外益处。氯己定二环己基氨基磺酸盐的简易合成产生了具有作为广谱抗菌剂的应用的材料。新发现的材料的最小抑菌浓度（MIC）与二葡萄糖酸氯己定对变形链球菌的抑制作用相当，同时由于环己基氨基磺酸盐的分子量小于葡萄糖酸盐，因此略微降低了药物的总量。另外，用生物活性人工甜味剂环己基氨基磺酸盐（即，N-环己基氨基磺酸酯）对应物产生可以潜在地增强味道特征的材料。
The synthesis, crystal structure, and antimicrobial efficacy are reported for a novel material comprising a 1:2 ratio of chlorhexidine (CHX) to N-cyclohexylsulfamate (i.e., artificial sweetener known as cyclamate). The chemical structure is unambiguously identified by incorporating a combination of single-crystal X-ray diffraction (SC-XRD), electrospray ionization mass spectrometry (ESI-MS), 1H nuclear magnetic resonance (NMR) spectroscopy, correlation spectroscopy (COSY), and attenuated total reflection Fourier-transform infrared spectroscopy (ATR-FTIR). The new material: 1) is amongst only several reported structures identified to date incorporating the vital chlorhexidine antimicrobial drug; 2) exhibits broad spectrum antimicrobial activity at concentrations less than 15 μg/mL; and 3) provides a unique delivery method for the essential active pharmaceutical ingredient (API). Furthermore, substitution of inactive gluconate with bioactive cyclamate counterion potentially provides the additional benefit of improving the taste profile of chlorhexidine. The facile synthesis of chlorhexidine dicyclamate yields a material with applications as a broad spectrum antimicrobial agent. The minimum inhibitory concentrations (MICs) of the newly discovered material is comparable to chlorhexidine digluconate for Streptococcus mutans while slightly reducing the overall amount of the drug since cyclamate exhibits a smaller molecular weight than gluconate. Additionally, the substitution of the biologically inert gluconate anion with the bioactive artificial sweetener cyclamate (i.e., N-cyclohexylsulfamate,) counterpart yields a material which can potentially enhance the taste profile.
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影响因子：
3.8
作者：
Cattaneo D;McCormick LJ;Cordes DB;Slawin AM;Morris RE
通讯作者：
Morris RE
影响因子：
3.5
作者：
LANG, NP;BRECX, MC
通讯作者：
BRECX, MC
影响因子：
5.1
作者：
Cavicchioli, Mauricio;Leite, Clarice Q. F.;Massabni, Antonio C.
通讯作者：
Massabni, Antonio C.
影响因子：
6.7
作者：
ADDY, M
通讯作者：
ADDY, M
影响因子：
7.6
作者：
EMILSON, CG
通讯作者：
EMILSON, CG