The role of amino acids on supramolecular co-assembly of naphthalenediimide–pyrene based hydrogelators†,RSC Advances

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The role of amino acids on supramolecular co-assembly of naphthalenediimide–pyrene based hydrogelators†
RSC Advances ( IF 3.9 ) Pub Date : 2018-04-19 00:00:00 , DOI: 10.1039/c8ra00929e
Srinivasa Rao Nelli _{1,

2,

3,

4} , Rajan Deepan Chakravarthy _{1,

2,

3,

4} , Mohammed Mohiuddin _{1,

2,

3,

4} , Hsin-Chieh Lin _{1,

2,

3,

4}

Affiliation

This report describes the two component self-assembly of π-capped amino acid hydrogelators (serine (S), aspartic acid (D), glutamic acid (E) or lysine (K)) prepared from pyrene (Py) based donor and naphthalenediimide (NDI) based acceptor molecules. The co-assembly can be triggered to form hydrogels by varying the pH conditions and the major driving forces behind the hydrogelation were found to be the formation of a strong charge-transfer (CT) complex and hydrogen bonding interactions at suitable pH conditions. The NDI–Py blends with matched donor/acceptor amino acid pairs undergo self-assembly under acidic pH conditions, whereas the blend (NDI–S + Py–K) with a mismatched amino acid pair forms a stable hydrogel under physiological pH conditions. UV-Vis, FTIR and rheological studies clearly indicate the formation and the stability of these CT-induced hydrogels. These hydrogels are of nanofibrous morphology with an average diameter of about 6–9 nm as evidenced by TEM analysis. In addition, this novel NDI–Py mixed component system exhibited good biocompatibility towards PC3 cells. Overall, since hydrogels based on CT-mediated two-component assemblies are very rare, our newly discovered NDI–Py hydrogels provide chemical insights into the design of a CT-induced hydrogelator and might facilitate various applications in biomedical engineering.

中文翻译：

氨基酸对萘二亚胺-芘基水凝胶的超分子共组装的作用†

本报告描述了由芘 (Py) 基供体和萘二亚胺制备的 π 封端氨基酸水凝胶剂（丝氨酸 (S)、天冬氨酸 (D)、谷氨酸 (E) 或赖氨酸 (K)）的两组分自组装（ NDI) 基于受体分子。通过改变 pH 条件可以触发共组装形成水凝胶，发现水凝胶化背后的主要驱动力是在合适的 pH 条件下形成强电荷转移 (CT) 复合物和氢键相互作用。NDI-Py 与匹配的供体/受体氨基酸对的混合物在酸性 pH 条件下进行自组装，而具有错配氨基酸对的混合物 (NDI-S + Py-K) 在生理 pH 条件下形成稳定的水凝胶。紫外可见，FTIR 和流变学研究清楚地表明了这些 CT 诱导的水凝胶的形成和稳定性。TEM 分析表明，这些水凝胶具有平均直径约为 6-9 nm 的纳米纤维形态。此外，这种新型 NDI-Py 混合组分体系对 PC3 细胞表现出良好的生物相容性。总的来说，由于基于 CT 介导的双组分组装的水凝胶非常罕见，我们新发现的 NDI-Py 水凝胶为 CT 诱导的水凝胶剂的设计提供了化学见解，并可能促进生物医学工程中的各种应用。

更新日期：2018-04-19

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