氧化还原响应型微乳液的制备及其在姜黄素包封中的应用。

Redox-responsive microemulsion: Fabrication and application to curcumin encapsulation.

机构信息

The Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical & Materials Engineering, Jiangnan University, Wuxi 214122, PR China; Key Laboratory of Green Cleaning Technology and Detergents of Zhejiang Province, Hangzhou 310056, PR China.

Petroleum Engineering Technology Research Institute of Shengli Oilfield, SINOPEC, Dongying, Shandong 257067, China.

出版信息

J Colloid Interface Sci. 2023 Oct;647:384-394. doi: 10.1016/j.jcis.2023.05.129. Epub 2023 May 21.

DOI:10.1016/j.jcis.2023.05.129

PMID:37269735

Abstract

HYPOTHESIS

Stimulus-responsive microemulsions have aroused significant attention because of their versatile and reversible switchability between stable and unstable states. However, most stimuli-responsive microemulsions are based on stimuli-responsive surfactants. We posit that the change in the hydrophilicity of a selenium-containing alcohol triggered by a mild redox reaction could also influence the stability of microemulsions and provide a new nanoplatform for the delivery of bioactive substances.

EXPERIMENTS

A selenium-containing diol (3,3'-selenobis(propan-1-ol), PSeP) was designed and used as a co-surfactant in a microemulsion with ethoxylated hydrogenated castor oil (HCO40), diethylene glycol monohexyl ether (DGME), 2-n-octyl-1-dodecanol (ODD) and water. The redox-induced transition in PSeP was characterized by H NMR, Se NMR, and MS. The redox-responsiveness of the ODD/HCO40/DGME/PSeP/water microemulsion was investigated through determination of a pseudo-ternary phase diagram, analysis by dynamic light scattering, and electrical conductivity, and its encapsulation performance was evaluated by determination of the solubility, stability, antioxidant activity, and skin penetrability of encapsulated curcumin.

FINDINGS

The redox conversion of PSeP enabled efficient switching of ODD/HCO40/DGME/PSeP/water microemulsions. Addition of oxidant (HO), oxidized PSeP into more hydrophilic PSeP-Ox (selenoxide), disrupting the emulsifying capacity of the combination of HCO40/DGME/PSeP, markedly reducing the monophasic microemulsion region in the phase diagram, and inducing phase separation in some formulations. Addition of reductant (NH·HO), reduced PSeP-Ox and restored the emulsifying capacity of the combination of HCO40/DGME/PSeP. In addition, PSeP-based microemulsions can significantly enhance the solubility in oil (by 23 times), stability, antioxidant capacity (DPPH∙ radical scavenging by 91.74 %), and skin penetrability of curcumin, showing clear potential for encapsulation and delivery of curcumin and other bioactive substances.

摘要

假设

刺激响应型微乳液因其在稳定态和不稳定态之间的多功能和可逆切换性而引起了广泛关注。然而，大多数刺激响应型微乳液都是基于刺激响应型表面活性剂。我们假设，通过温和的氧化还原反应触发的含硒醇的亲水性变化也会影响微乳液的稳定性，并为生物活性物质的输送提供新的纳米平台。

实验

设计并使用一种含硒二醇（3,3'-硒代双（丙-1-醇），PSeP）作为微乳液的助表面活性剂，与乙氧基化氢化蓖麻油（HCO40）、二乙二醇单己基醚（DGME）、2-辛基-1-十二醇（ODD）和水一起使用。通过 H NMR、Se NMR 和 MS 对 PSeP 的氧化还原诱导转变进行了表征。通过测定拟三元相图、动态光散射分析和电导率研究了 ODD/HCO40/DGME/PSeP/water 微乳液的氧化还原响应性，并通过测定包裹姜黄素的溶解度、稳定性、抗氧化活性和皮肤渗透性来评价其包裹性能。

结果

PSeP 的氧化还原转化使 ODD/HCO40/DGME/PSeP/water 微乳液的高效切换成为可能。添加氧化剂（HO），将 PSeP 氧化成更亲水的 PSeP-Ox（硒氧化物），破坏了 HCO40/DGME/PSeP 的乳化能力，显著减少了相图中的单相微乳液区域，并在一些配方中引起相分离。添加还原剂（NH·HO），将 PSeP-Ox 还原并恢复 HCO40/DGME/PSeP 的乳化能力。此外，基于 PSeP 的微乳液可以显著提高姜黄素在油中的溶解度（提高 23 倍）、稳定性、抗氧化能力（DPPH·自由基清除率达 91.74%）和皮肤渗透性，显示出对姜黄素和其他生物活性物质的封装和输送的明显潜力。