Macrocyclic Supramolecular Assemblies Based on Hyaluronic Acid and Their Biological Applications,Accounts of Chemical Research

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Macrocyclic Supramolecular Assemblies Based on Hyaluronic Acid and Their Biological Applications
Accounts of Chemical Research ( IF 16.4 ) Pub Date : 2022-11-15 , DOI: 10.1021/acs.accounts.2c00462
Zhixue Liu ₁ , Wenjing Lin ₁ , Yu Liu _{1,

2,

3}

Affiliation

Hyaluronic acid (HA), which contains multiple carboxyl, hydroxyl, and acetylamino groups and is an agent that targets tumors, has drawn great attention in supramolecular diagnosis and treatment research. It can not only assemble directly with macrocyclic host–guest complexes through hydrogen bonding and electrostatic interactions but also can be modified with macrocyclic compounds or functional guest molecules by an amidation reaction and used for further assembly. Macrocycles play a main role in the construction of supramolecular drug carriers, targeted imaging agents, and hydrogels, such as cyclodextrins and cucurbit[n]urils, which can encapsulate photosensitizers, drugs, or other functional guest molecules via host–guest interactions. Therefore, the formed supramolecular assemblies can respond to various stimuli, such as enzymes, light, electricity, and magnetism for controlled drug delivery, enhance the luminescence intensity of the assembly, and improve drug loading capacity. In addition, the nanosupramolecular assembly formed with HA can also improve the biocompatibility of drugs, reduce drug toxicity and side effects, and enhance cell permeability; thus, the assembly has extensive application value in biomedical research. This Account mainly focuses on macrocyclic supramolecular assemblies based on HA, especially their biological applications and progress in the field, and these assemblies include (i) guest-modified HA, such as pyridinium-, adamantane-, peptide-, and other functional-group-modified HA, along with their cyclodextrin and cucurbit[n]uril assemblies; (ii) macrocycle-modified HA, such as HA modified with cyclodextrins and cucurbit[n]uril derivatives and their assembly with various guests; (iii) direct assembly between unmodified HA and cyclodextrin- or cucurbit[n]uril-based host–guest complexes. Particularly, we discussed the important role of macrocyclic host–guest complexes in HA-based supramolecular assembly, and the roles included improving the water solubility and efficacy of hydrophobic drugs, enhancing the luminescent intensity of assemblies, inducing room temperature phosphorescence and providing energy transfer systems, constructing multi-stimulus-responsive supramolecular assemblies, and in situ formation of hydrogels. Additionally, we believe that obtaining in-depth knowledge of these HA-based macrocyclic supramolecular assemblies and their biological applications encompasses many challenges regarding drug carriers, targeted imaging agents, wound healing, and biomedical soft materials and would certainly contribute to the rapid development of supramolecular diagnosis and treatment.

中文翻译：

基于透明质酸的大环超分子组装及其生物学应用

透明质酸(HA)含有多个羧基、羟基和乙酰氨基，是一种靶向肿瘤的药物，在超分子诊断和治疗研究中引起了极大的关注。它不仅可以通过氢键和静电相互作用与大环主客体复合物直接组装，还可以通过酰胺化反应用大环化合物或功能性客体分子修饰，用于进一步组装。大环化合物在超分子药物载体、靶向显像剂和水凝胶的构建中发挥主要作用，如环糊精和葫芦素[ n]urils，它可以通过主客体相互作用封装光敏剂、药物或其他功能性客体分子。因此，所形成的超分子组装体可以响应酶、光、电、磁等多种刺激来控制药物递送，增强组装体的发光强度，提高载药量。此外，与HA形成的纳米超分子组装体还可以提高药物的生物相容性，降低药物毒副作用，增强细胞通透性；因此，该组装体在生物医学研究中具有广泛的应用价值。本刊主要关注基于HA的大环超分子组装体，特别是其生物学应用和领域进展，这些组装体包括（i）客体修饰的HA，如吡啶鎓-、金刚烷-、n ]uril 程序集；(ii) 大环修饰的HA，例如用环糊精和葫芦[ n ]脲衍生物修饰的HA及其与各种客体的组装；(iii) 未修饰的 HA 和基于环糊精或葫芦[n]脲的主客体复合物之间的直接组装。特别是，我们讨论了大环主客体复合物在基于 HA 的超分子组装中的重要作用，其作用包括提高疏水性药物的水溶性和功效、增强组装体的发光强度、诱导室温磷光和提供能量转移系统, 构建多刺激响应超分子组装体, 并原位水凝胶的形成。此外，我们相信，深入了解这些基于 HA 的大环超分子组装体及其生物学应用，将在药物载体、靶向成像剂、伤口愈合和生物医学软材料等方面面临许多挑战，必将有助于超分子的快速发展。诊断和治疗。

更新日期：2022-11-15

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