Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

Lepage, Mathieu L.; Mirloup, Antoine; Ripoll, Manon; Stauffert, Fabien; Bodlenner, Anne; Ziessel, Raymond; Compain, Philippe

doi:10.3762/bjoc.11.74

Cited by 23 publications

(19 citation statements)

References 76 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There are a large number of water-soluble BODIPY derivatives containing diverse water-solubilizing groups, including sulfonic acids, 20 zwitterionic ammonium-sulfonic acid substituents, 21 phosphonates, 22 polyethylene glycol (PEG), 23 and sugars. 24 Water-soluble synthetic chlorins and bacteriochlorins, containing phosphonate, 25,26 PEG, 26,27 carboxylates, 26,28 or ammonium salts, 26,29 were also reported. However, we presume, that synthesis of arrays containing water-solubilizing groups on both BODIPY and hydroporphyrins would be prohibitively labor- and cost-intensive, since it will add several synthetic and purification steps to already lengthy synthesis of hydrophobic arrays.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

et al. 2017

View full text Add to dashboard Cite

BODIPY-hydroporphyrin energy transfer arrays allow for development of family of fluorophores featuring a common excitation band at 500 nm, tunable excitation band in deep red/near-infrared window, and tunable emission. Their biomedical applications are contingent upon retaining their optical properties in aqueous environment. Amphiphilic arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their optical and fluorescence properties were determined in organic solvents and aqueous surfactants. The first series of arrays contains BODIPYs with PEG substituents attached to the boron, whereas in the second series, PEG substituents are attached to the aryl at the meso positions of BODIPY. For both series of arrays, excitation of BODIPY at 500 nm results in an efficient energy transfer to and bright emission of hydroporphyrin in deep-red (640–660 nm) or near-infrared (740–760 nm) spectral windows. In aqueous non-ionic surfactants (Triton X-100 and Tween 20) arrays from the second series exhibit significant quenching of fluorescence, whereas properties of arrays from the first series are comparable to those observed in polar organic solvents. Reported arrays possess large effective Stokes shift (115 – 260 nm), multiple excitation wavelengths, and narrow, tunable deep-red/near-IR fluorescence in aqueous surfactants, and are promising candidates for a variety of biomedical-related applications.

show abstract

Section: Introductionmentioning

confidence: 99%

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

et al. 2017

View full text Add to dashboard Cite

show abstract

“…The authors used a cyanine dye conjugated with Tilmanocept to specifically bind mannose receptors of macrophages, facilitating the delivery of a radiopharmaceutic drug . Multivalent clusters of iminosugars conjugated with pyrene or boron‐dipyrromethene cores exhibited fluorescence spectra applicable in cell imaging . As discussed earlier, multivalent iminosugars have been intensively tested as promising pharmacological chaperones.…”

Section: Cell/tissue Targetingmentioning

confidence: 99%

Nanotechnology in Glycomics: Applications in Diagnostics, Therapy, Imaging, and Separation Processes

Dosekova

Filip

Bertók

et al. 2016

Medicinal Research Reviews

View full text Add to dashboard Cite

This review comprehensively covers the most recent achievements (from 2013) in the successful integration of nanomaterials in the field of glycomics. The first part of the paper addresses the beneficial properties of nanomaterials for the construction of biosensors, bioanalytical devices, and protocols for the detection of various analytes, including viruses and whole cells, together with their key characteristics. The second part of the review focuses on the application of nanomaterials integrated with glycans for various biomedical applications, that is, vaccines against viral and bacterial infections and cancer cells, as therapeutic agents, for in vivo imaging and nuclear magnetic resonance imaging, and for selective drug delivery. The final part of the review describes various ways in which glycan enrichment can be effectively done using nanomaterials, molecularly imprinted polymers with polymer thickness controlled at the nanoscale, with a subsequent analysis of glycans by mass spectrometry. A short section describing an active glycoprofiling by microengines (microrockets) is covered as well.

show abstract

“…Earlier, BODIPYs containing various hydrophilic groups have been used as imaging probes [22][23][24], and PDT agents [25][26][27]. Recently, cell internalization of some BODIPY-based fluorescent dyes bearing carbohydrate residues have M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 5 been studied by fluorescence microscopy [28,29], while synthesis and photophysical properties of some BODIPY-conjugated iminosugar clusters [30] as well as of lactosylceramide [31] have also been reported. In another study, some BODIPYs were grafted on a carbohydrate platform to synthesize artificial light-harvesting antenna [32].…”

Section: Introductionmentioning

confidence: 99%

Syntheses and photodynamic activity of some glucose-conjugated BODIPY dyes

Shivran

Tyagi

Mula

et al. 2016

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

Cited by 23 publications

References 76 publications

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

Nanotechnology in Glycomics: Applications in Diagnostics, Therapy, Imaging, and Separation Processes

Syntheses and photodynamic activity of some glucose-conjugated BODIPY dyes

Contact Info

Product

Resources

About