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Antimicrobial Activity with Enhanced Mechanical Properties in Phenylalanine-Based Chiral Coassembled Hydrogels: The Influence of Pyridine Hydrazide Derivatives
ACS Applied Bio Materials ( IF 4.6 ) Pub Date : 2020-03-02 , DOI: 10.1021/acsabm.0c00075 Auphedeous Y Dang-I 1 , Tingting Huang 2 , Nabila Mehwish 1 , Xiao-Qiu Dou 1 , Li Yang 1 , Vincent Mukwaya 1 , Chao Xing 1 , Shuangjun Lin 2 , Chuan-Liang Feng 1
ACS Applied Bio Materials ( IF 4.6 ) Pub Date : 2020-03-02 , DOI: 10.1021/acsabm.0c00075 Auphedeous Y Dang-I 1 , Tingting Huang 2 , Nabila Mehwish 1 , Xiao-Qiu Dou 1 , Li Yang 1 , Vincent Mukwaya 1 , Chao Xing 1 , Shuangjun Lin 2 , Chuan-Liang Feng 1
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Hydrazide derivatives are known to display a wide range of biological properties including antimicrobial activities, hence making them desirable candidates for soft biomaterials. Herein, we report chiral supramolecular coassembled hydrogels obtained from two phenylalanine gelators (L/DPF and B2L/D) and two dicarbohydrazide molecules (pyridine-2,6-dicarbohydrazide (PDH) and (2,2′-bipyridine)-5,5′-dicarbohydrazide (BDH)) that exhibited enhanced mechanical properties, chirality modulation, and antimicrobial activity. Four lines of coassembled hydrogels were obtained (i.e., L/DPF–PDH, L/DPF–BDH, B2L/D–PDH, and B2L/D–BDH) through hydrogen bonding and π–π stacking with some level of an interpenetrating network, as revealed by the structural characterization analysis. Mechanical properties were significantly improved, especially in the case of hybrid gels involving BDH, with improved average elastic modulus (G′) values of 3430 and 3167 Pa for DPF–BDH and B2D–BDH (1:3, molar concentration) over 140 and 1680 Pa for DPF and B2D gelators, respectively. This was attributed to the improved π–π stacking and interpenetrating network due to the bipyridine group and its ease to form fibrous precipitates in the process of heating and cooling to room temperature. PDH, on the other hand, was able to modulate chirality in the L/DPF gelator due to its more planar and less bulky nature and showed antimicrobial activity against Pseudomonas aeruginosa (Gram-negative). Interestingly, when PDH was coassembled with the B2L/D gelator, the hybrid gels exhibited antimicrobial activity against Staphylococcus aureus (Gram-positive) and P. aeruginosa (Gram-negative) by virtue of a synergistic effect of the gelator and the azomethine group of PHD. Hence, by moving from bipyridine (BDH) to pyridine (PDH) as a core structure in the hydrazide molecules, the resulting hybrid hydrogels exhibited desirable properties of antimicrobial activity and improved mechanical attributes.
中文翻译：
苯丙氨酸基手性共组装水凝胶中具有增强机械性能的抗菌活性：吡啶酰肼衍生物的影响
已知酰肼衍生物显示出广泛的生物学特性，包括抗菌活性，因此使其成为软生物材料的理想候选者。在此，我们报道了由两种苯丙氨酸凝胶剂（L/DPF 和 B2L/D）和两种二甲酰肼分子（吡啶-2,6-二甲酰肼 (PDH) 和 (2,2'-联吡啶)-5,5）获得的手性超分子共组装水凝胶'-二碳酰肼 (BDH)) 表现出增强的机械性能、手性调节和抗菌活性。获得了四行共组装的水凝胶（即., L/DPF-PDH, L/DPF-BDH, B2L/D-PDH, and B2L/D-BDH) 通过氢键和 π-π 堆叠与一定程度的互穿网络，如结构表征分析所示. 机械性能显着提高，特别是在涉及 BDH 的混合凝胶的情况下，平均弹性模量（G'）DPF-BDH 和 B2D-BDH（1:3，摩尔浓度）的值分别为 3430 和 3167 Pa，DPF 和 B2D 凝胶剂分别超过 140 和 1680 Pa。这归因于联吡啶基团改善了 π-π 堆叠和互穿网络，并且在加热和冷却至室温的过程中易于形成纤维状沉淀物。另一方面，PDH 能够调节 L/DPF 凝胶剂中的手性，因为它具有更平坦和体积更小的性质，并显示出对铜绿假单胞菌（革兰氏阴性）的抗菌活性。有趣的是，当 PDH 与 B2L/D 凝胶剂共组装时，混合凝胶表现出对金黄色葡萄球菌（革兰氏阳性）和铜绿假单胞菌的抗菌活性（革兰氏阴性）由于凝胶剂和 PHD 的偶氮甲碱基团的协同作用。因此，通过从联吡啶（BDH）转变为吡啶（PDH）作为酰肼分子的核心结构，得到的杂化水凝胶表现出理想的抗菌活性和改善的机械性能。
更新日期：2020-04-23
中文翻译：
苯丙氨酸基手性共组装水凝胶中具有增强机械性能的抗菌活性：吡啶酰肼衍生物的影响
已知酰肼衍生物显示出广泛的生物学特性，包括抗菌活性，因此使其成为软生物材料的理想候选者。在此，我们报道了由两种苯丙氨酸凝胶剂（L/DPF 和 B2L/D）和两种二甲酰肼分子（吡啶-2,6-二甲酰肼 (PDH) 和 (2,2'-联吡啶)-5,5）获得的手性超分子共组装水凝胶'-二碳酰肼 (BDH)) 表现出增强的机械性能、手性调节和抗菌活性。获得了四行共组装的水凝胶（即., L/DPF-PDH, L/DPF-BDH, B2L/D-PDH, and B2L/D-BDH) 通过氢键和 π-π 堆叠与一定程度的互穿网络，如结构表征分析所示. 机械性能显着提高，特别是在涉及 BDH 的混合凝胶的情况下，平均弹性模量（G'）DPF-BDH 和 B2D-BDH（1:3，摩尔浓度）的值分别为 3430 和 3167 Pa，DPF 和 B2D 凝胶剂分别超过 140 和 1680 Pa。这归因于联吡啶基团改善了 π-π 堆叠和互穿网络，并且在加热和冷却至室温的过程中易于形成纤维状沉淀物。另一方面，PDH 能够调节 L/DPF 凝胶剂中的手性，因为它具有更平坦和体积更小的性质，并显示出对铜绿假单胞菌（革兰氏阴性）的抗菌活性。有趣的是，当 PDH 与 B2L/D 凝胶剂共组装时，混合凝胶表现出对金黄色葡萄球菌（革兰氏阳性）和铜绿假单胞菌的抗菌活性（革兰氏阴性）由于凝胶剂和 PHD 的偶氮甲碱基团的协同作用。因此，通过从联吡啶（BDH）转变为吡啶（PDH）作为酰肼分子的核心结构，得到的杂化水凝胶表现出理想的抗菌活性和改善的机械性能。
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