Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università di Messina, Via F. Stagno d'Alcontres 31, 98166 Messina, Italy.
Org Biomol Chem. 2022 Apr 6;20(14):2742-2763. doi: 10.1039/d1ob02459k.
Luminescent BODIPY-sugar probes have stimulated the attention of researchers for the potential applications of such molecular systems in bio-imaging. The presence of carbohydrate units confers unique structural and biological features, beside enhancement of water solubility and polarity. On the other hand, BODIPY (BOronDiPYrromethene) derivatives represent eclectic and functional luminescent molecules because of their outstanding photophysical properties. This article provides a review on the synthesis and applications of BODIPY-linked glycosyl probes in which the labelling of complex carbohydrates with BODIPY allowed the disclosing of their behaviour or where the sugar constitutes a recognition element for specific targeting probes, or, finally, in which the stereochemical characteristics of the carbohydrate hydroxyl groups play as structural elements for assembling more than one photoactive subunit, resulting in functional supramolecular molecules with modulable properties. We describe the methods we have used to construct various multiBODIPY molecular systems capable of functioning as artificial antennas exhibiting extremely efficient and fast photo-induced energy transfer. Some of these systems have been designed to allow the modulation of energy transfer efficiency and emission color, and intensity dependent on their position within a biological matrix. Finally, future perspectives for such BODIPY-based functional supramolecular sugar systems are also highlighted.
发光 BODIPY-糖探针激发了研究人员的兴趣，因为这类分子系统在生物成像中有潜在的应用。糖基单元的存在赋予了这些分子独特的结构和生物学特性，同时还提高了它们的水溶性和极性。另一方面，BODIPY（BOronDiPYrromethene）衍生物是一种多功能的发光分子，因为它们具有出色的光物理性质。本文综述了 BODIPY 连接的糖基探针的合成和应用，其中 BODIPY 标记复杂碳水化合物可以揭示其行为，或者糖基作为特定靶向探针的识别元件，或者最后，碳水化合物羟基的立体化学特征作为组装多个光活性亚基的结构元件，形成具有可调节性质的功能超分子分子。我们描述了我们用于构建各种多 BODIPY 分子系统的方法，这些系统能够作为人工天线发挥作用，表现出极其高效和快速的光诱导能量转移。其中一些系统的设计允许根据它们在生物基质中的位置来调节能量转移效率和发射颜色和强度。最后，还强调了基于 BODIPY 的功能性超分子糖系统的未来展望。
