Supraamphiphilic Systems Based on Metallosurfactant and Calix[4]resorcinol: Self-Assembly and Drug Delivery Potential,Inorganic Chemistry

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Supraamphiphilic Systems Based on Metallosurfactant and Calix[4]resorcinol: Self-Assembly and Drug Delivery Potential
Inorganic Chemistry ( IF 4.3 ) Pub Date : 2020-11-25 , DOI: 10.1021/acs.inorgchem.0c02833
Ruslan Kashapov ₁ , Yuliya Razuvayeva _{1,

2} , Albina Ziganshina ₁ , Tatiana Sergeeva ₁ , Svetlana Lukashenko ₁ , Anastasiia Sapunova ₁ , Alexandra Voloshina ₁ , Nadezda Kashapova ₁ , Irek Nizameev _{1,

2} , Vadim Salnikov _{3,

4} , Sufia Ziganshina ₅ , Bulat Gareev ₄ , Lucia Zakharova _{1,

2}

Affiliation

Metallic amphiphiles are used as building blocks in the construction of nanoscale superstructures, where the hydrophobic effects induce the self-assembly of the nanoparticles of interest. However, the influence of synergizing multiple chemical interactions on an effective design of these structures mostly remains an open question. In this regard, supraamphiphilic systems based on flexible surfactant molecules and rigid macrocycles are being actively developed, but there are few works on the interaction between metallosurfactants and macrocycles. In the present work, the self-assembly and biological properties of a metallosurfactant with calixarene were studied for the first time. The metallosurfactant, a complex between lanthanum nitrate and two 4-aza-1-hexadecylazoniabicyclo[2.2.2]octane bromide units, and calix[4]resorcinol containing sulfonate groups on the upper rim were used to form a novel supraamphiphilic composition. The system formed was studied using a variety of physicochemical methods, including spectrophotometry, NMR, XRF, and dynamic and electrophoretic light scattering. It was found that the most optimal tetraanionic calix[4]resorcinol to dicationic metallosurfactant molar ratio, leading to mixed aggregation upon ion pair complexation, is 2:3. The mixed aggregates formed in the pentamolar concentration range were able to encapsulate hydrophilic substrates, including the anticancer drug cisplatin, the pure form of which is more cytotoxic toward healthy cells than toward diseased cells. Interestingly, the drug loaded into the macrocycle–metallosurfactant particles was less cytotoxic to a healthy Chang liver cell line and more cytotoxic to tumor M-HeLa cells. This selectivity depends on the amount of cisplatin added. The more drug is added to the macrocycle–metallosurfactant composition, the greater the biological activity against cancer cells. Taking into account that the appearance of resistance of cancer cells to drugs, especially to cisplatin, is one of the most important problems in treatment, the results of this work envisage the potential application of a mixed macrocycle–metallosurfactant system for the design of therapeutic cisplatin compositions.

中文翻译：

基于金属表面活性剂和Calix [4]间苯二酚的超两亲体系：自组装和药物传递潜力

金属两亲物被用作构建纳米级超结构的基础，其中疏水作用诱导了感兴趣的纳米颗粒的自组装。然而，增效多种化学相互作用对这些结构有效设计的影响仍然是一个悬而未决的问题。在这方面，基于挠性表面活性剂分子和刚性大环化合物的超两亲体系正在积极开发中，但是关于金属表面活性剂与大环化合物之间相互作用的工作很少。在本工作中，首次研究了具有杯芳烃的金属表面活性剂的自组装和生物学特性。金属表面活性剂，硝酸镧和两个4-氮杂-1-十六烷基氮杂双环[2.2.2]辛烷溴化物单元之间的络合物，和杯状[4]间苯二酚含磺酸盐基团的上边缘被用来形成一个新的超两亲组成。使用各种物理化学方法研究了形成的系统，包括分光光度法，NMR，XRF以及动态和电泳光散射。发现最理想的四阴离子杯[4]间苯二酚与顺式金属表面活性剂的摩尔比为2：3，导致离子对络合时混合聚集。在五摩尔浓度范围内形成的混合聚集体能够包裹亲水性底物，包括抗癌药顺铂，其纯净形式对健康细胞的细胞毒性比对患病细胞的细胞毒性更大。有趣的是加载到大环金属表面活性剂颗粒中的药物对健康的Chang肝细胞系的细胞毒性较小，而对肿瘤M-HeLa细胞的细胞毒性更大。这种选择性取决于顺铂的添加量。添加到大环-金属表面活性剂成分中的药物越多，针对癌细胞的生物活性就越大。考虑到癌细胞对药物，特别是对顺铂的耐药性是治疗中最重要的问题之一，这项工作的结果设想了大环-金属表面活性剂混合系统在顺铂治疗设计中的潜在应用成分。对癌细胞的生物学活性越强。考虑到癌细胞对药物，特别是对顺铂的耐药性是治疗中最重要的问题之一，这项工作的结果设想了大环-金属表面活性剂混合系统在顺铂治疗设计中的潜在应用成分。对癌细胞的生物学活性越强。考虑到癌细胞对药物，特别是对顺铂的耐药性是治疗中最重要的问题之一，这项工作的结果设想了大环-金属表面活性剂混合系统在顺铂治疗设计中的潜在应用成分。

更新日期：2020-12-21

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