Water-Soluble BODIPY Derivatives

Niu, Song; Ulrich, Gilles; Ziessel, Raymond; Kiss, Agnèta; Renard, Pierre; Romieu, Anthony

doi:10.1021/ol900302n

Cited by 175 publications

(116 citation statements)

References 26 publications

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“…15 Ligands with a net formal charge of zero have also been explored such as zwitterionic sulfobetaines ( 4 ). 16 While all approaches yield BODIPY dyes with improved water solubility, the applicability of these derivatives for live cell and in vivo imaging is limited by the ionic character of the solubilizing groups, which impair membrane permeability, and often result in a significantly increased size of the fluorescent tag. Similarly, modification with multiple PEG-groups ( 5 ) can improve aqueous solubility, again at the cost of increased size (in some examples the solubilizing groups account for >80% of the total molecular weight).…”

mentioning

confidence: 99%

Monoalkoxy BODIPYs—A Fluorophore Class for Bioimaging

Courtis¹,

Santos

Guan

et al. 2014

Bioconjugate Chem.

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Small molecule fluorophores are indispensable tools for modern biomedical imaging techniques. In this report, we present the development of a new class of BODIPY dyes based on an alkoxy-fluoro-boron-dipyrromethene core. These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties. MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling. Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.

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mentioning

confidence: 99%

Monoalkoxy BODIPYs—A Fluorophore Class for Bioimaging

Courtis¹,

Santos

Guan

et al. 2014

Bioconjugate Chem.

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“…The excitation spectra did display a slight shift compared to the absorption spectra. This may be due to the presence of some aggregates, a problem frequently encountered with aromatic organic dyes in aqueous solutions [69–70]. Addition of 2.5% of a surfactant such as sodium dodecyl sulfate (SDS) improves the spectral overlap with the absorption spectra (Fig.…”

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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“…Hence, smart and efficient strategies are required to overcome this issue, which is currently being challenged by some groups. [86][87][88] The photostability of BODIPY sometimes becomes a point of argument.…”

Section: ·3 Challenges Concerning the Improvement Of Bodipymentioning

confidence: 99%