Fluorescent labeling of alkyl chains of phosphocholine lipids by one-pot TMS cleavage-click reaction

Hornillos, Valentı́n; Amat‐Guerri, F.; Acuña, A. Ulises

doi:10.1016/j.jphotochem.2012.06.005

Cited by 7 publications

(3 citation statements)

References 43 publications

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“…A convergent approach comprising the attachment of azide-armed iminosugars 4 [ 11 – 12 ] on polyalkyne “clickable” scaffolds 5 and 6 via Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) was performed for achieving our synthetic goals ( Fig. 2 ) [ 56 – 57 ]. With the objective of increasing water solubility and chemical stability in biological medium, triyne 6b , an analogue of F-BODIPY-based scaffold 6a was prepared by replacing the fluoro groups on the boron center with ethynyl tetra(ethylene glycol)methyl groups [ 58 – 59 ].…”

Section: Resultsmentioning

confidence: 99%

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

Lepage

Mirloup²,

Ripoll

et al. 2015

Beilstein J. Org. Chem.

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SummaryThe synthesis and photophysical properties of the first examples of iminosugar clusters based on a BODIPY or a pyrene core are reported. The tri- and tetravalent systems designed as molecular probes and synthesized by way of Cu(I)-catalysed azide–alkyne cycloadditions are fluorescent analogues of potent pharmacological chaperones/correctors recently reported in the field of Gaucher disease and cystic fibrosis, two rare genetic diseases caused by protein misfolding.

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Section: Resultsmentioning

confidence: 99%

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

Lepage

Mirloup²,

Ripoll

et al. 2015

Beilstein J. Org. Chem.

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“…Hornillos et al (Figure 3.31). 88 Although taught in second year chemistry, alkyne hydration is not commonly reported as an issue in click reactions, so this result was surprising. this was confirmed using spectroscopic techniques and X-ray diffraction.…”

Section: Conjugated Bodipy Systems In Click Reactionsmentioning

confidence: 99%

“…80 Hornillos et al, reported fluorescent labelling of lipids utilizing the click technique (Figure 3.12). 88 Lipid labelling was carried out by the click reaction between an alkyne BODIPY and its azide-phospholipid complement to afford 3.8, and as well as an analogue model lipid 3.9. A TMSprotected BODIPY was deprotected with AgBF4 to yield the unprotected alkyne which then underwent an in situ reaction with an azide to afford 3.8 in 74% yield.…”

Section: Cuaac Mechanismmentioning

confidence: 99%

Exploring Bodipy Dyes in Light-Harvesting, Energy Transfer and Bio-Inspired Probe Designs

Sritharan

2024

Preprint

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<p>Attempts to mimic Nature and create artificial photosynthetic systems has transformed from an active chemical curiosity to a full-blown research pursuit, owing to our need for sustainable energy generation. To this end, this thesis explores the use of the dye, BODIPY (4-4’-difluoro-4-bora-3a,4a-diaza-s-indacene). BODIPY dyes have gained considerable attention owing to their highly desirable properties, such as strong absorption, fluorescence quantum yields, good chemical and photo-stability. These desirable physiochemical properties have led to materials that can be used for chemosensors, biological labeling agents, fluorescent switches, laser dyes, and organic sensitizers. For this thesis, a pentamethylBODIPY (2.1a) derivative was further functionalized in order to examine its potential for a myriad of applications.</p> <p>Energy extraction in terms of dye-sensitized solar cells (DSSCs) requires electronically asymmetric molecules as building blocks. In Chapter 2, pentamethylBODIPY (2.1a) was modified using Schiff-base chemistry to create a family of dye building blocks. In this chapter, mono ß-substitution was used to break symmetry in this potential BODIPY building block, thus tuning the electronic and optical properties.</p>

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Functionalized Phospholipid Molecular Platform: Use for Production of Cationic Fluorescent Lipids

Berchel¹,

Haelters²,

Afonso³

et al. 2013

Eur J Org Chem

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International audienceFluorescent amphiphilic phospholipids (neutral or cationic) in which fluorescent probes are contained in the lipid domain were synthesized via phosphoramide intermediates possessing two distinct lipid chains. One of these lipid chains is ω-functionalized with an azide or alkyne group, and this is subsequently used to introduce a fluorescent probe by Huisgen cycloaddition. Five different fluorescent probes (naphthalimide, dansyl, fluoresceine, Nile red, and coumarin) were considered in this study. These neutral and cationic fluorescent lipids were included at a 1 % molar ratio with a selected cationic lipid (KLN47) to produce liposomal solutions that were characterized by dynamic light scattering and zeta potential measurements

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Fluorescent labeling of alkyl chains of phosphocholine lipids by one-pot TMS cleavage-click reaction

Cited by 7 publications

References 43 publications

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

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

Exploring Bodipy Dyes in Light-Harvesting, Energy Transfer and Bio-Inspired Probe Designs

Functionalized Phospholipid Molecular Platform: Use for Production of Cationic Fluorescent Lipids

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