Cappelli Andrea, Paolino Marco, Reale Annalisa, Razzano Vincenzo, Grisci Giorgio, Giuliani Germano, Donati Alessandro, Bonechi Claudia, Lamponi Stefania, Mendichi Raniero, Battiato Salvatore, Samperi Filippo, Makovec Francesco, Licciardi Mariano, Depau Lorenzo, Botta Chiara
Dipartimento di Biotecnologie, Chimica e Farmacia and European Research Centre for Drug Discovery and Development, Università degli Studi di Siena Via A. Moro 2 53100 Siena Italy
Istituto per lo Studio delle Macromolecole (CNR) Via A. Corti 12 20133 Milano Italy.
RSC Adv. 2018 Feb 6;8(11):5864-5881. doi: 10.1039/c7ra12543g. eCollection 2018 Feb 2.
In order to develop a technology platform based on two natural compounds from biorenewable resources, a short series of hyaluronan (HA) copolymers grafted with propargylated ferulic acid (HA-FA-Pg) were designed and synthesized to show different grafting degree values and their optical properties were characterized in comparison with reference compounds containing the same ferulate fluorophore. Interestingly, these studies revealed that the ferulate fluorophore was quite sensitive to the restriction of intramolecular motion and its introduction into the rigid HA backbone, as in HA-FA-Pg graft copolymers, led to higher photoluminescence quantum yield values than those obtained with the isolated fluorophore. Thus, the propargyl groups of HA-FA-Pg derivatives were exploited in the coupling with oleic acid through a biocompatible nona(ethylene glycol) spacer as an example of the possible applications of this technology platform. The resulting HA-FA-NEG-OA materials showed self-assembling capabilities in aqueous environment. Furthermore, HA-FA-NEG-OA derivatives have been shown to interact with phospholipid bilayers both in liposomes and living cells, retaining their fluorogenic properties and showing a high degree of cytocompatibility and for this reason they were proposed as potential biocompatible self-assembled aggregates forming new materials for biomedical applications.
为了开发一个基于两种来自生物可再生资源的天然化合物的技术平台，设计并合成了一系列短链的接枝了炔丙基化阿魏酸的透明质酸（HA）共聚物（HA-FA-Pg），以展示不同的接枝度值，并与含有相同阿魏酸荧光团的参考化合物相比，对其光学性质进行了表征。有趣的是，这些研究表明，阿魏酸荧光团对分子内运动的限制相当敏感，并且将其引入刚性的HA主链中，如在HA-FA-Pg接枝共聚物中，导致其光致发光量子产率值高于分离的荧光团。因此，以该技术平台的可能应用为例，利用HA-FA-Pg衍生物的炔丙基通过生物相容性的九聚（乙二醇）间隔基与油酸偶联。所得的HA-FA-NEG-OA材料在水性环境中显示出自组装能力。此外，已证明HA-FA-NEG-OA衍生物在脂质体和活细胞中均与磷脂双层相互作用，保留其荧光特性，并显示出高度的细胞相容性，因此它们被提议作为潜在的生物相容性自组装聚集体，形成用于生物医学应用的新材料。
