Strategies for penicillin V dendronization with cationic carbosilane dendrons and study of antibacterial properties
Strategies for penicillin V dendronization with cationic carbosilane dendrons and study of antibacterial properties
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DOI：
10.1139/cjc-2017-0059
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发表时间：
2017-09-01
影响因子：
1.1
通讯作者：
Javier de la Mata, F.
中科院分区：
文献类型：
--
作者：
Fuentes-Paniagua, Elena;Hernandez-Ros, Jose M.;Javier de la Mata, F.
讨论了合成在焦点处含有抗生素青霉素 V 钾盐 (PenVK) 的阳离子碳硅烷树枝的策略。这种化合物的制备需要使用框架中不含N或S等供体原子的系统，因为它们的存在有利于青霉素β-内酰胺环的破裂。评估了外围含有铵基团和焦点处含有 PenV 部分的新树突对革兰氏阳性金黄色葡萄球菌菌株的抗菌活性。将这些结果与游离 PenVK（一种在焦点处没有青霉素部分的相关阳离子树突）获得的结果进行比较，并且还与最后一个树突与游离 PenV 的等摩尔混合物进行比较。获得的数据表明，一方面，与游离PenVK相比，PenV与阳离子树枝的缀合或相互作用降低了其活性。另一方面，由于该衍生物中酯键的断裂，青霉素树枝能够在酯酶存在下释放抗生素。
Strategies to synthesize a cationic carbosilane dendron containing the antibiotic penicillin V potassium salt (PenVK) at the focal point are discussed. The preparation of such a compound requires the use of systems with no donor atoms such as N or S in their framework, because their presence favours the rupture of the penicillin beta-lactam ring. The antibacterial activity of the new dendron containing ammonium groups, at the periphery, and the PenV moiety, at the focal point, against gram-positive Staphylococcus aureus strains was evaluated. These results were compared with those obtained for free PenVK, a related cationic dendron without a penicillin moiety at the focal point, and also compared with an equimolar mixture of this last dendron with free PenV. The data obtained indicate that, on one hand, the conjugation or interaction of PenV with cationic dendrons reduces its activity in comparison with free PenVK. On the other hand, the penicillin dendron is able to release the antibiotic in the presence of esterease, due to the breaking of the ester bond in this derivative.