A Trp-BODIPY cyclic peptide for fluorescence labelling of apoptotic bodies

Subirós‐Funosas, Ramon; Mendive‐Tapia, Lorena; Sot, Jesús; Pound, John D.; Barth, Nicole; Varela, Yaiza R.; Goñi, Félix M.; Paterson, Mary; Gregory, Christopher D.; Alberício, Fernando; Dransfield, Ian; Lavilla, Rodolfo; Vendrell, Marc

doi:10.1039/c6cc07879f

Cited by 70 publications

(49 citation statements)

References 30 publications

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“…[6,[9][10][11] Reflectingt hese advantages, BODIPY dyes have been employed as molecular probes for bioimaging, molecular detection, photocaging,p hotodynamic therapy and as antimicrobials and laser dyes. [17][18][19][20] However,f or fluorophores containing the BODIPYc ore, the absorption intensity is often compromised in analogues where the absorbance l max has been shifted towards the far-red region. Similarly,acompromise between the fluorescence l max and the intensity is often observed.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Relationship between BODIPY Structure and Spectroscopic Properties to Design Fluorophores for Bioimaging

Donnelly

Offenbartl‐Stiegert

Marín-Beloqui

et al. 2019

Chemistry A European J

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Designingc hromophores for biological applications requires af undamental understanding of how the chemical structure of ac hromophore influences its photophysical properties. We here describe the synthesis of al ibrary of BODIPY dyes, exploring diversity at variouspositions around the BODIPY core. The results show that the nature and positiono fs ubstituents have ad ramatic effect on the spectroscopicp roperties. Substituting in ah eavy atom or adjusting the size and orientation of ac onjugated system provides am eans of alteringt he spectroscopic profiles with high precision. Thei nsight from the structure-activity relationshipw as appliedt od evise an ew BODIPY dye with rationally designed photochemical properties including absorptiont owardst he near-infraredr egion. The dye also exhibiteds witch-onf luorescencet oe nable visualisation of cells with high signal-to-noise ratio without washing-outo f unboundd ye. The BODIPY-based probe is non-cytotoxic and compatible with staining procedures including cell fixation and immunofluorescencemicroscopy.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

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Section: Introductionmentioning

confidence: 99%

Exploring the Relationship between BODIPY Structure and Spectroscopic Properties to Design Fluorophores for Bioimaging

Donnelly

Offenbartl‐Stiegert

Marín-Beloqui

et al. 2019

Chemistry A European J

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“…This biohybrid was able to bind in apoptotic bodies from BL2 human lymphoma cells. [108] Concerning the linkage of other PSs to HSA/BSA, there are diverse examples described in the literature. Nanospheres composed by biohybrids of HSA, poly-L-lysine and chlorin e 6 have been tested in HeLa, B16 and MCF-7 cell lines, evaluating the phototoxic effect, obtaining good results and showing no harmful effects in dark conditions.…”

Section: Other Porphyrinoidsmentioning

confidence: 99%

Emerging Perspectives on Applications of Porphyrinoids for Photodynamic Therapy and Photoinactivation of Microorganisms

Almeida-Marrero¹,

González‐Delgado²,

Torres³

2019

MHC

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The use of photosensitizers (PSs) in photodynamic therapy (PDT) and photodynamic inactivation of microorganisms (PDI), as well in other biomedical techniques as medical imaging, represents a challenge for improving given properties that are desired in a biological media, such as water solubility, lack of aggregation and biocompatibility, among others. This review shows the most recent and important examples of the conjugation of photosensitizers to different biomolecules to achieve this goal. The manuscript is written in an accessible way in order to give a general vision of the recent advances stimulating at the same time the curiosity of the reader.

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“…We have also recently employed the amino acid 1 for the preparation of cyclic peptides as fluorescent reagents for imaging apoptotic bodies. 24 These imaging experiments should be considered as a template set of directions to be modified for the readers in their experiments of choice, which may vary depending on the instrumentation (e.g. confocal microscope) and cell systems used.…”

Section: Overview Of the Proceduresmentioning

confidence: 99%

Preparation of a Trp-BODIPY fluorogenic amino acid to label peptides for enhanced live-cell fluorescence imaging

et al. 2017

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Fluorescent peptides are valuable tools for live-cell imaging because of the high specificity of peptide sequences for their biomolecular targets. When preparing fluorescent versions of peptides, labels must be introduced at appropriate positions in the sequences to provide suitable reporters while avoiding any impairment of the molecular recognition properties of the peptides. This protocol describes the preparation of the tryptophan (Trp)-based fluorogenic amino acid Fmoc-Trp(C-BODIPY)-OH and its incorporation into peptides for live-cell fluorescence imaging-an approach that is applicable to most peptide sequences. Fmoc-Trp(C-BODIPY)-OH contains a BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorogenic core, which works as an environmentally sensitive fluorophore, showing high fluorescence in lipophilic conditions. It is attached to Trp via a spacer-free C-C linkage, resulting in a labeled amino acid that can mimic the molecular interactions of Trp, enabling wash-free imaging. This protocol covers the chemical synthesis of the fluorogenic amino acid Fmoc-Trp(C-BODIPY)-OH (3-4 d), the preparation of the labeled antimicrobial peptide BODIPY-cPAF26 by solid-phase synthesis (6-7 d) and its spectral and biological characterization as a live-cell imaging probe for different fungal pathogens. As an example, we include a procedure for using BODIPY-cPAF26 for wash-free imaging of fungal pathogens, including real-time visualization of Aspergillus fumigatus (5 d for culturing, 1-2 d for imaging).

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A Trp-BODIPY cyclic peptide for fluorescence labelling of apoptotic bodies

Cited by 70 publications

References 30 publications

Exploring the Relationship between BODIPY Structure and Spectroscopic Properties to Design Fluorophores for Bioimaging

Exploring the Relationship between BODIPY Structure and Spectroscopic Properties to Design Fluorophores for Bioimaging

Emerging Perspectives on Applications of Porphyrinoids for Photodynamic Therapy and Photoinactivation of Microorganisms

Preparation of a Trp-BODIPY fluorogenic amino acid to label peptides for enhanced live-cell fluorescence imaging

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