A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation.
Ana M. Gómez,Clara Uriel,Ainhoa Oliden-Sánchez,Jorge Bañuelos,Inmaculada García-Moreno,J. Cristobal Lopez +5 more
TLDR
In this paper, Ferrier-type C-glycosylation of 8-aryl-1,3,5,7-tetramethyl BODIPYs with commercially available tri-O-acetyl-d-glucal followed by saponification is presented.Abstract:
Novel, linker-free, BODIPY-carbohydrate derivatives containing sugar residues at positions C2 and C6 are efficiently obtained by, hitherto unreported, Ferrier-type C-glycosylation of 8-aryl-1,3,5,7-tetramethyl BODIPYs with commercially available tri-O-acetyl-d-glucal followed by saponification. This transformation, which involves the electrophilic aromatic substitution (SEAr) of the dipyrrin framework with an allylic oxocarbenium ion, provides easy access to BODIPY-carbohydrate hybrids with excellent photophysical properties and a weaker tendency to aggregate in concentrated water solutions.read more
Citations
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A BODIPY-O-glycoside based near-infrared fluorescent sensor for serum albumin.
Neelam Shivran,Mrunesh Koli,Goutam Chakraborty,Amit P. Srivastava,Subrata Chattopadhyay,Soumyaditya Mula,Soumyaditya Mula +6 more
TL;DR: In this paper, a near-infrared emitting BODIPY-O-glycoside dye was used as a turn-on emission sensor for serum albumin detection and quantification.
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Bringing Color to Sugars: The Chemical Assembly of Carbohydrates to BODIPY Dyes.
Ana M. Gómez,J. Cristobal Lopez +1 more
TL;DR: In this article, a collection of available methods for the synthesis of BODIPY-carbohydrate hybrids, with a focus on the chemical transformations on the core of the BODY core, is presented.
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4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications
Juan Alberto Marco Ventura,Clara Uriel,Ana María Gómez,Edurne Avellanal-Zaballa,Jorge Bañuelos,Esther Rebollar,Inmaculada García-Moreno,J. P. Lopez +7 more
TL;DR: The presence of F or CN substituents at boron in BODIPYs causes a dramatic effect on their reactivity, which allows their chemoselective postfunctionalization as mentioned in this paper .
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Synthesis of carbohydrate–BODIPY hybrids
TL;DR: In this paper , a per-alkylated 8-(2-hydroxy-methylphenyl)-4,4′-dicyano-BODIPY derivative, which withstands glycosylation and protection/deprotection reaction conditions without decomposition, was used in the stepwise synthesis of two fluorescently labeled trisaccharides.
References
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BODIPY dyes and their derivatives: syntheses and spectroscopic properties.
Aurore Loudet,Kevin Burgess +1 more
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Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging
TL;DR: This review highlights the advances in the development of far-red to NIR fluorescent probes since 2000, and the probes are classified according to their organic dye platforms into various categories, including cyanines, rhodamine analogues, BODIPYs, squaraines, and other types.
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Light Microscopy Techniques for Live Cell Imaging
TL;DR: A brief overview of the main approaches to live cell imaging is given, with some mention of their pros and cons.
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Structural modification strategies for the rational design of red/NIR region BODIPYs
TL;DR: This review focuses on classifying different types of long wavelength absorbing BODIPY dyes based on the wide range of structural modification methods that have been adopted, and on tabulating their spectral and photophysical properties.
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BODIPY-based probes for the fluorescence imaging of biomolecules in living cells
TL;DR: Advances in the development of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based fluorescent probes for biological studies over the past decade are covered.