A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting
A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting
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DOI：
10.1016/j.ijpharm.2017.05.023
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发表时间：
2017-10-15
影响因子：
5.8
通讯作者：
Sortino, Salvatore
中科院分区：
文献类型：
--
作者：
Benkovics, Gabor;Perez-Lloret, Marta;Sortino, Salvatore
这篇文章报道了一种新型阳离子、水溶性β-环糊精（β-CD）结合物的设计、合成和光化学性质，该结合物在β-CD支架的初级侧内整合了蒽部分和硝基苯胺衍生物。蒽和硝基苯胺发色团之间的光诱导能量转移有效地抑制了蒽单元的荧光。用可见光激发引发从硝基苯胺发色团释放一氧化氮（NO），伴随着蒽荧光的伴随复兴，蒽荧光充当用于检测释放的NO的量的光学报告物。此外，蒽部分光生单线态氧（O-1（2）），从而释放NO。该共轭物也能够在β CD空腔内容纳疏水客体，如通过使用萘作为模型化合物所证明的。鉴于NO和O-1（2）作为抗癌和抗菌物质的关键作用，本发明的β CD衍生物代表了针对多模式治疗应用的生物制药研究中的进一步研究的有趣候选物。(C)2017爱思唯尔B. V.保留所有权利。
This contribution reports the design, synthesis and photochemical properties of a novel cationic, water soluble, beta-cyclodextrin (beta CD) conjugate integrating an anthracene moiety and a nitroaniline derivative within the primary side of the beta CD scaffold. Photoinduced energy transfer between the anthracene and the nitroaniline chromophores effectively suppresses the fluorescence of the anthracene unit. Excitation with visible light triggers the release of nitric oxide (NO) from the nitroaniline chromophore, accompanied to the concomitant revival of the anthracene fluorescence, which acts as an optical reporter for detecting the amount of the NO released. Furthermore, the anthracene moiety photogenerates singlet oxygen (O-1(2)) sequentially to NO release. The conjugate is also able to accommodate hydrophobic guests within the beta CD cavity, as proven by using naphthalene as a model compound. In view of the key role NO and O-1(2) play as anticancer and antibacterial species, the present beta CD derivative represents an intriguing candidate for further studies in biopharmaceutical research addressed to multimodal therapeutic applications. (C) 2017 Elsevier B.V. All rights reserved.