Bodipy-carbohydrate systems: synthesis and bio-applications

被引:16
作者
Barattucci, Anna [1 ]
Gangemi, Chiara M. A. [1 ]
Santoro, Antonio [1 ]
Campagna, Sebastiano [1 ]
Puntoriero, Fausto [1 ]
Bonaccorsi, Paola [1 ]
机构
[1] Univ Messina, Dipartimento Sci Chim Biol Farmaceut & Ambientali, Via F Stagno dAlcontres 31, I-98166 Messina, Italy
关键词
ENANTIOSELECTIVE SYNTHESIS; PHOTOPHYSICAL PROPERTIES; PHOTOAFFINITY PROBES; TARGETED DELIVERY; CLICK CHEMISTRY; ENERGY-TRANSFER; DYES; FLUORESCENCE; LIGHT; INTERNALIZATION;
D O I
10.1039/d1ob02459k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 in vivo 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.
引用
收藏
页码:2742 / 2763
页数:23
相关论文
共 97 条
[1]  
[Anonymous], 2014, ANGEW CHEM, V126, P11155, DOI DOI 10.1002/ANGE.201406842
[2]   Discrimination of cellular developmental states focusing on glycan transformation and membrane dynamics by using BODIPY-tagged lactosyl ceramides [J].
Arai, Kenta ;
Ohtake, Atsuko ;
Daikoku, Shusaku ;
Suzuki, Katsuhiko ;
Ito, Yukishige ;
Kabayama, Kazuya ;
Fukase, Koichi ;
Kanie, Yoshimi ;
Kanie, Osamu .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (19) :3724-3733
[3]   Artificial, molecular-based light-harvesting antenna systems made of metal dendrimers and multibodipy species [J].
Arrigo, Antonino ;
La Ganga, Giuseppina ;
Nastasi, Francesco ;
Serroni, Scolastica ;
Santoro, Antonio ;
Santoni, Marie-Pierre ;
Galletta, Maurilio ;
Campagna, Sebastiano ;
Puntoriero, Fausto .
COMPTES RENDUS CHIMIE, 2017, 20 (03) :209-220
[4]   BODIPY on Board of Sugars: A Short Enlightened Journey up to the Cells [J].
Barattucci, Anna ;
Campagna, Sebastiano ;
Papalia, Teresa ;
Galletta, Maurilio ;
Santoro, Antonio ;
Puntoriero, Fausto ;
Bonaccorsi, Paola .
CHEMPHOTOCHEM, 2020, 4 (09) :647-658
[5]   Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products [J].
Barattucci, Anna ;
Aversa, Maria Chiara ;
Mancuso, Aurora ;
Salerno, Tania Maria Grazia ;
Bonaccorsi, Paola .
MOLECULES, 2018, 23 (05)
[6]   Bioorthogonal click chemistry: Covalent labeling in living systems [J].
Baskin, Jeremy M. ;
Bertozzi, Carolyn R. .
QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12) :1211-1219
[7]   Design of BODIPY dyes as triplet photosensitizers: electronic properties tailored for solar energy conversion, photoredox catalysis and photodynamic therapy [J].
Bassan, Elena ;
Gualandi, Andrea ;
Cozzi, Pier Giorgio ;
Ceroni, Paola .
CHEMICAL SCIENCE, 2021, 12 (19) :6607-6628
[8]   Lighting the way ahead with boron dipyrromethene (Bodipy) dyes [J].
Benniston, Andrew C. ;
Copley, Graeme .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2009, 11 (21) :4124-4131
[9]   Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging [J].
Biagiotti, Giacomo ;
Puric, Edvin ;
Kriselj, Ana ;
Weiss, Matjaz ;
Mravljak, Janez ;
Gellini, Cristina ;
Lay, Luigi ;
Chiodo, Fabrizio ;
Anderluh, Marko ;
Cicchi, Stefano ;
Richichi, Barbara ;
Urbancic, Iztok .
BIOORGANIC CHEMISTRY, 2021, 109
[10]   Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core [J].
Boens, Noel ;
Verbelen, Bram ;
Ortiz, Maria J. ;
Jiao, Lijuan ;
Dehaen, Wim .
COORDINATION CHEMISTRY REVIEWS, 2019, 399