Synthesis of Water-Soluble Far-Red-Emitting Amphiphilic BODIPY Dyes

Bardon, Kevin M.; Selfridge, Scott; Adams, Dany S.; Minns, Richard A.; Pawle, Robert H.; Adams, Timothy C.; Takiff, Larry

doi:10.1021/acsomega.8b01487

Cited by 11 publications

(14 citation statements)

References 36 publications

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“…Several strategies have been reported to improve the water solubility of BODIPY dyes such as the introduction of ionizable functional groups – carboxylate, sulfonate or ammonium groups – or the functionalization with carbohydrates, dendrimers, poly(ethylene glycol) (PEG) chains or combinations thereof . PEG functionalization can be even employed for NIR‐emitting BODIPYs . Alternatively, it is also possible to obtain highly fluorescent objects with hydrophobic BODIPY dyes in aqueous media if they are encapsulated in polymeric nanoparticles .…”

Section: Introductionmentioning

confidence: 99%

“…Especially problematic is the case of NIR-emitting BODIPYs since these chromophores tend to have larger aromatic structures and are thus more hydrophobic. [7,31] Several strategies have been reported to improve the water solubility of BODIPY dyes [8] such as the introduction of ionizable functional groups -carboxylate, sulfonate [18,32,33] or ammonium [33,34] groups -or the functionalization with carbohydrates, [35,36] dendrimers, [37,38] poly(ethylene glycol) (PEG) chains [18,21,24,39] or combinations thereof. [40,41] PEG functionalization can be even employed for NIR-emitting BODIPYs.…”

Section: Introductionmentioning

confidence: 99%

“…[40,41] PEG functionalization can be even employed for NIR-emitting BODIPYs. [19,22,23,33,42,43] Alternatively, it is also possible to obtain highly fluorescent objects with hydrophobic BODIPY dyes in aqueous media if they are encapsulated in polymeric nanoparticles. [44] Ziessel et al have recently performed an interesting comparative study of the ability of different hydrophilic groups to improve water solubility for a series of BODIPYs and derived a water-solubility scale by determining the partition coefficient and fluorescence quantum yield for each polar BODIPY dye.…”

Section: Introductionmentioning

confidence: 99%

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On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

et al. 2019

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The tendency of boron‐dipyrromethene (BODIPY) dyes to associate in water is well known, and usually a cause for inferior fluorescence properties. Synthetic efforts to chemically improve BODIPYs’ water solubility and minimize this problem have been numerous in the past. However, a deeper understanding of the phenomena responsible for fluorescence quenching is still required. Commonly, the spectroscopic behaviour in aqueous media has been attributed to aggregate or excimer formation, with such works often centring on a single BODIPY family. Herein, we provide an integrating discussion including very diverse types of BODIPY dyes. Our studies revealed that even subtle structural changes can distinctly affect the association behaviour of the fluorophores in water, involving different photophysical processes. The palette of behaviour found ranges from unperturbed emission, to the formation of H or J aggregates and excimers, to the involvement of tightly bound, pre‐formed excimers. These results are a first step to a more generalized understanding of spectroscopic properties vs. structure, facilitating future molecular design of BODIPYs, especially as probes for biological applications.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

et al. 2019

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“…This large Stokes shift (around 180 nm, see Figure S2 ) enables minimization of the self-quenching effect and leads to an enhanced signal-to-noise ratio 41 . This represents a major advantage compared to most of the commercially available far-red emitting fluorophores; for instance: borondipyrromethene (BODIPY) 42 , 43 , cyanine or rhodamine dyes 44 , 45 , that display Stokes shifts limited to ~ 20 nm.…”

Section: Discussionmentioning

confidence: 99%

Multiscale fluorescent tracking of immune cells in the liver with a highly biocompatible far-red emitting polymer probe

Daniel

Dubreil

Fleurisson

et al. 2020

Sci Rep

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The development of innovative immune cell therapies relies on efficient cell tracking strategies. For this, multiscale fluorescence-based analyses of transferred cells into the host with complementary techniques, including flow cytometry for high-throughput cell analysis and two-photon microscopy for deep tissue imaging would be highly beneficial. Ideally, cells should be labelled with a single fluorescent probe combining all the properties required for these different techniques. Due to the intrinsic autofluorescence of most tissues and especially the liver, far-red emission is also an important asset. However, the development of far-red emitting probes suitable for two-photon microscopy and compatible with clearing methods to track labelled immune cells in thick samples, remains challenging. A newly-designed water-soluble far-red emitting polymer probe, 19K-6H, with a large Stokes shift, was thus evaluated for the tracking of primary immune CD8 T cells. These cells, prepared from mouse spleen, were efficiently labelled with the 19K-6H probe, which was internalized via endocytosis and was highly biocompatible at concentrations up to 20 μM. Labelled primary CD8 T cells were detectable in culture by both confocal and two-photon microscopy as well as flow cytometry, even after 3 days of active proliferation. Finally, 19K-6H-labelled primary CD8 T cells were injected to mice in a classical model of immune mediated hepatitis. The efficient tracking of the transferred cells in the liver by flow cytometry (on purified non-parenchymal cells) and by two-photon microscopy on 800 μm thick cleared sections, demonstrated the versatility of the 19K-6H probe.

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“…However, such BODIPY derivatives are highly hydrophobic, which makes conjugation with targeting moieties, including peptides and antibodies, very difficult. To improve their water solubility, the introduction of charged or water-soluble groups to BODIPY compounds has been attempted. , …”

Section: Introductionmentioning

confidence: 99%

Effect of Short PEG on Near-Infrared BODIPY-Based Activatable Optical Probes

et al. 2020

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Targeted near-infrared (NIR) fluorescence probes are playing a significant role in biomedical imaging because NIR penetrates deeper into tissues and is associated with reduced autofluorescence compared to visible light fluorescence probes. Long-wavelength emitting 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is an attractive platform for synthesizing NIR fluorophores because of its high photostability, high molar absorption coefficient, and sharp absorption and emission spectra. However, its lipophilicity hampers the conjugation chemistry necessary to add targeting moieties. In this study, we synthesized a novel NIR BODIPY derivative, NMP14. Substitutions of ethylene-bridged pyrrole units at the 3- or 5-position of the parent BODIPY chromophore result in a red shift of more than 200 nm. However, NMP14 cannot be conjugated to antibodies because of its hydrophobicity. Therefore, we synthesized NMP13 by adding short poly(ethylene glycol) to NMP14 and successfully conjugated NMP13 to cetuximab and trastuzumab. In vitro microscopic studies showed that NMP13 conjugated antibodies were activated after internalization and lysosomal processing, which means that NMP13 acts as an activatable probe only turning on after cellular internalization. After the administration of NMP13 conjugated antibodies, mice tumors were detected with high tumor to background ratios for a long period. These results suggest that NMP13 has potential as an activatable fluorescence probe for further clinical applications.

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Synthesis of Water-Soluble Far-Red-Emitting Amphiphilic BODIPY Dyes

Cited by 11 publications

References 36 publications

On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

Multiscale fluorescent tracking of immune cells in the liver with a highly biocompatible far-red emitting polymer probe

Effect of Short PEG on Near-Infrared BODIPY-Based Activatable Optical Probes

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