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Tailored-BODIPY/Amphiphilic Cyclodextrin Nanoassemblies with PDT Effectiveness
Langmuir ( IF 3.7 ) Pub Date : 2018-06-25 00:00:00 , DOI: 10.1021/acs.langmuir.8b01049 R. Zagami 1 , G. Sortino 1 , E. Caruso 2 , M. C. Malacarne 2 , S. Banfi 2 , S. Patanè 3 , L. Monsù Scolaro 4, 5 , A. Mazzaglia 1
Langmuir ( IF 3.7 ) Pub Date : 2018-06-25 00:00:00 , DOI: 10.1021/acs.langmuir.8b01049 R. Zagami 1 , G. Sortino 1 , E. Caruso 2 , M. C. Malacarne 2 , S. Banfi 2 , S. Patanè 3 , L. Monsù Scolaro 4, 5 , A. Mazzaglia 1
Affiliation
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Amphiphilic cyclodextrins (aCDs) are an intriguing class of carrier systems which, recently, have been proposed to deliver porphyrinoids and anticancer drugs or combined dose of both for dual therapeutic applications. The design of nanoassemblies based on aCD and photosensitizers (PSs) aims to preserve the photodynamic therapy (PDT) efficacy of PS, reducing the tendency of PS to self-aggregate, without affecting the quantum yield of singlet oxygen (1O2) production, and, not less importantly, minimizing dark toxicity and reducing photosensitization effects. With this idea in mind, in this paper, we focus on nanoassemblies between a non-ionic aCD (SC6OH) and halo-alkyl tailored iodinated boron-dipyrromethenes (BODIPY) dye, a class of molecules which recently have been successfully proposed as a stimulating alternative to porphyrinoids for their high photodynamic efficacy. Nanoassemblies of BODIPY/aCD ([email protected]) were prepared in different aqueous media by evaporation of mixed organic film of aCD and BODIPY, hydration, and sonication. The nanostructures were characterized, measuring their hydrodynamic diameter and ξ-potential and also evaluating their time-stability in biological relevant media. Taking advantage of emissive properties of the not-iodinated BODIPY analogue (BL01), nanoassemblies based on aCD and BL01 were investigated as model system to get insight on entanglement of BODIPY in the amphiphile in aqueous dispersion, pointing out that BODIPY is well-entrapped in monomeric form (τ ≅ 6.5 ns) within the colloidal carriers. Also morphology and fluorescence emission properties were elucidated after casting the solution on glass. [email protected] is easily detectable in cytoplasm of HCT116 cell lines, evidencing the remarkable intracellular penetration of this nanoassembly similar to free BODIPY. On the same cell lines, the photodynamically active assembly BL01I/aCD shows toxicity upon irradiation. Despite the fact that free BL01I is more PDT active than its assembly, aCD can modulate the cell uptake of BODIPY, pointing out the potential of this system for in vivo PDT application.
中文翻译：
具有PDT功效的量身定制的BODIPY /两亲环糊精纳米组件
两性环糊精（aCDs）是一类引人入胜的载体系统，最近已提出将其输送卟啉类和抗癌药或两者的联合剂量以用于双重治疗。基于aCD和光敏剂（PSs）的纳米组件的设计旨在保持PS的光动力疗法（PDT）的功效，减少PS自聚集的趋势，而不影响单线态氧的量子产率（1 O 2）生产，并且同样重要的是，最大程度地降低黑暗毒性并降低光敏作用。考虑到这一想法，在本文中，我们将重点放在非离子aCD（SC6OH）和卤代烷基定制的碘化硼二吡咯烷酮（BODIPY）染料之间的纳米组装，该染料最近已被成功地提出来作为刺激分子是卟啉类药物的替代品，因为它们具有很高的光动力学功效。通过蒸发aCD和BODIPY的混合有机膜，水合和超声处理，在不同的水性介质中制备BODIPY / aCD的纳米组件（[受电子邮件保护]）。对纳米结构进行了表征，测量了它们的流体动力学直径和ξ势，还评估了它们在生物相关介质中的时间稳定性。利用未碘化的BODIPY类似物（BL01）的发射特性，研究了基于aCD和BL01的纳米组件作为模型系统，以了解BODIPY在水分散液中的两亲物之间的纠缠，并指出BODIPY以单体形式（τ≅6.5 ns）很好地包裹在胶体载体中。在将溶液浇铸在玻璃上之后，还阐明了形态和荧光发射性质。[电子邮件保护]在HCT116细胞系的细胞质中很容易检测到，证明了这种纳米组件与游离BODIPY一样具有显着的细胞内渗透性。在相同的细胞系上，光动力活性组件BL01I / aCD在照射时显示出毒性。尽管事实上，游离BL01I的PDT活性高于其组装体，但aCD可以调节BODIPY的细胞摄取，指出该系统在体内PDT应用中的潜力。
更新日期：2018-06-25
中文翻译：
具有PDT功效的量身定制的BODIPY /两亲环糊精纳米组件
两性环糊精（aCDs）是一类引人入胜的载体系统，最近已提出将其输送卟啉类和抗癌药或两者的联合剂量以用于双重治疗。基于aCD和光敏剂（PSs）的纳米组件的设计旨在保持PS的光动力疗法（PDT）的功效，减少PS自聚集的趋势，而不影响单线态氧的量子产率（1 O 2）生产，并且同样重要的是，最大程度地降低黑暗毒性并降低光敏作用。考虑到这一想法，在本文中，我们将重点放在非离子aCD（SC6OH）和卤代烷基定制的碘化硼二吡咯烷酮（BODIPY）染料之间的纳米组装，该染料最近已被成功地提出来作为刺激分子是卟啉类药物的替代品，因为它们具有很高的光动力学功效。通过蒸发aCD和BODIPY的混合有机膜，水合和超声处理，在不同的水性介质中制备BODIPY / aCD的纳米组件（[受电子邮件保护]）。对纳米结构进行了表征，测量了它们的流体动力学直径和ξ势，还评估了它们在生物相关介质中的时间稳定性。利用未碘化的BODIPY类似物（BL01）的发射特性，研究了基于aCD和BL01的纳米组件作为模型系统，以了解BODIPY在水分散液中的两亲物之间的纠缠，并指出BODIPY以单体形式（τ≅6.5 ns）很好地包裹在胶体载体中。在将溶液浇铸在玻璃上之后，还阐明了形态和荧光发射性质。[电子邮件保护]在HCT116细胞系的细胞质中很容易检测到，证明了这种纳米组件与游离BODIPY一样具有显着的细胞内渗透性。在相同的细胞系上，光动力活性组件BL01I / aCD在照射时显示出毒性。尽管事实上，游离BL01I的PDT活性高于其组装体，但aCD可以调节BODIPY的细胞摄取，指出该系统在体内PDT应用中的潜力。
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