Benkovics Gábor, Perez-Lloret Marta, Afonso Damien, Darcsi András, Béni Szabolcs, Fenyvesi Éva, Malanga Milo, Sortino Salvatore
CycloLab, Cyclodextrin R&D Ltd, Illatos út 7, H-1097 Budapest, Hungary; Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavová 8, 128 43 Prague 2, Czech Republic.
Laboratory of Photochemistry, Department of Drug Sciences, University of Catania, I-95125, Italy.
Int J Pharm. 2017 Oct 15;531(2):614-620. doi: 10.1016/j.ijpharm.2017.05.023. Epub 2017 May 11.
This contribution reports the design, synthesis and photochemical properties of a novel cationic, water soluble, β-cyclodextrin (βCD) conjugate integrating an anthracene moiety and a nitroaniline derivative within the primary side of the βCD 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) sequentially to NO release. The conjugate is also able to accommodate hydrophobic guests within the βCD cavity, as proven by using naphthalene as a model compound. In view of the key role NO and O play as anticancer and antibacterial species, the present βCD derivative represents an intriguing candidate for further studies in biopharmaceutical research addressed to multimodal therapeutic applications.
本论文报道了一种新型阳离子水溶性β-环糊精（βCD）共轭物的设计、合成及光化学性质，该共轭物在βCD支架的主面上整合了蒽部分和硝基苯胺衍生物。蒽与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。可见光激发会触发硝基苯胺发色团释放一氧化氮（NO），同时蒽荧光随之恢复，蒽荧光可作为检测释放的NO量的光学报告分子。此外，蒽部分在释放NO后会依次光生成单线态氧（O）。以萘为模型化合物证明，该共轭物还能够在βCD腔内容纳疏水性客体。鉴于NO和O作为抗癌和抗菌物质所起的关键作用，目前的βCD衍生物是生物制药研究中用于多模态治疗应用进一步研究的一个有趣候选物。
