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Efficient acid-catalyzed (18) F/(19) F fluoride exchange of BODIPY dyes.

ABSTRACT: Fluorine-containing fluorochromes are important validation agents for positron emission tomography imaging compounds, as they can be readily validated in cells by fluorescence imaging. In particular, the (18) F-labeled BODIPY-FL fluorophore has emerged as an important platform, but little is known about alternative (18) F-labeling strategies or labeling on red-shifted fluorophores. In this study we explore acid-catalyzed (18) F/(19) F exchange on a range of commercially available N-hydroxysuccinimidyl ester and maleimide BODIPY fluorophores. We show this method to be a simple and efficient (18) F-labeling strategy for a diverse span of fluorescent compounds, including a BODIPY-modified PARP-1 inhibitor, and amine- and thiol-reactive BODIPY fluorophores.

SUBMITTER: Keliher EJ

PROVIDER: S-EPMC4145401 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Efficient acid-catalyzed (18) F/(19) F fluoride exchange of BODIPY dyes.

Keliher Edmund J EJ Klubnick Jenna A JA Reiner Thomas T Mazitschek Ralph R Weissleder Ralph R

ChemMedChem 20140305 7

Fluorine-containing fluorochromes are important validation agents for positron emission tomography imaging compounds, as they can be readily validated in cells by fluorescence imaging. In particular, the (18) F-labeled BODIPY-FL fluorophore has emerged as an important platform, but little is known about alternative (18) F-labeling strategies or labeling on red-shifted fluorophores. In this study we explore acid-catalyzed (18) F/(19) F exchange on a range of commercially available N-hydroxysuccin ...[more]

PMID: 24596307

Similar Datasets

Expeditious, mechanochemical synthesis of BODIPY dyes.

Project description:BODIPY dyes have been synthesized under solvent-free or essentially solvent-free conditions, within about 5 minutes in an open-to-air setup by using a pestle and mortar, with yields that are comparable to those obtained via traditional routes that typically require reaction times of several hours to days.

| S-EPMC3678757 | biostudies-other

Lewis acid-assisted isotopic 18F-19F exchange in BODIPY dyes: facile generation of positron emission tomography/fluorescence dual modality agents for tumor imaging.

Project description:Positron emission tomography (PET) is a powerful technique for imaging biological pathways in vivo, particularly those that are key targets in disease processes. In contrast, fluorescence imaging has demonstrated to be a superior method for image-guided surgery, such as tumor removal. Although the integration of PET and optical imaging could provide an attractive strategy for patient management, there is a significant shortage of established platforms/methods for PET/optical probe construction. In this study, various reaction conditions were explored to develop a simple and fast method allowing for the introduction of [(18)F]-fluoride into BODIPY dyes. Through a systematic optimization of the reaction conditions, we found that BODIPY dyes, including commercial amine-reactive BODIPY succinimidyl esters, may be converted into their radioactive analogues in the matter of minutes via a (18)F-(19)F isotopic exchange reaction promoted by a Lewis acid such as SnCl4. An integrin-targeting RGD peptide was also conjugated with [(18)F]BODIPY® R6G , derived from the commercially available BODIPY® R6G fluorescent tag, to provide a [(18)F]-RGD conjugate in 82% yield. In vivo evaluation of this imaging probe showed a discernible tumor uptake in the U87MG xenograft model. The dual modality imaging properties of the probe was confirmed by ex vivo fluorescence and microPET imaging experiments. In summary, in the matter of minutes, BODIPY dyes were converted into their "hot" radioactive analogues via a (18)F-(19)F isotopic exchange reaction promoted by a Lewis acid. This approach, which can be applied to commercial BODIPY dyes, provides easy access to positron emission tomography/fluorescence dual modality imaging agents.

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Functionalization of 3,5,8-trichlorinated BODIPY dyes.

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Aza-BODIPY dyes with enhanced hydrophilicity.

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Photochemical Properties and Stability of BODIPY Dyes.

Project description:The present study is devoted to the combined experimental and theoretical description of the photophysical properties and photodegradation of the new boron-dipyrromethene (BODIPY) derivatives obtained recently for biomedical applications, such as bacteria photoinactivation (Piskorz et al., Dyes and Pigments 2020, 178, 108322). Absorption and emission spectra for a wide group of solvents of different properties for the analyzed BODIPY derivatives were investigated in order to verify their suitability for photopharmacological applications. Additionally, the photostability of the analyzed systems were thoroughly determined. The exposition to the UV light was found first to cause the decrease in the most intensive absorption band and the appearance of the hypsochromically shifted band of similar intensity. On the basis of the chromatographic and computational study, this effect was assigned to the detachment of the iodine atoms from the BODIPY core. After longer exposition to UV light, photodegradation occurred, leading to the disappearance of the intensive absorption bands and the emergence of small intensity signals in the strongly blue-shifted range of the spectrum. Since the most intensive bands in original dyes are ascribed to the molecular core bearing the BF2 moiety, this result can be attributed to the significant cleavage of the BF2 ring. In order to fully characterize the obtained molecules, the comprehensive computational chemistry study was performed. The influence of the intermolecular interactions for their absorption in solution was analyzed. The theoretical data entirely support the experimental outcomes.

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Efficient Colorimetric Fluoride Anion Chemosensors With Varied Colors Based on Simple Aminobenzodifuranone Organic ?-Conjugated Dyes.

Project description:High selectivity and sensitivity detection of fluoride anions (F-) in an organic solution by the naked eye has always been a challenge. In this investigation, a simple compound based on aminobenzodifuranone (ABDF) was designed and synthesized. Deprotonation of the amino moiety caused by F- is responsible for a color change from dark blue to various colors (colorless, yellow, orange, and red) in different common organic solvents due to a blue shift over 200 nm in the UV/Vis spectrum. The color change is quite visible to the naked eye under ambient light. The detection limit for F- can reach a concentration of as low as 5.0 × 10-7 M with high selectivity, even in a solution containing multiple anions.

| S-EPMC7175790 | biostudies-literature

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C-H functionalization and their photophysical properties.

Project description:A series of α- and β-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C-H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S0-S1 transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials.

| S-EPMC7136566 | biostudies-literature

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins' Little Sisters.

Project description:The photodynamic properties of a series of non-halogenated, dibrominated and diiodinated BODIPYs with a phthalimido or amino end modification on the phenoxypentyl and phenoxyoctyl linker in the meso position were investigated. Halogen substitution substantially increased the singlet oxygen production based on the heavy atom effect. This increase was accompanied by a higher photodynamic activity against skin melanoma cancer cells SK-MEL-28, with the best compound reaching an EC50 = 0.052 ± 0.01 µM upon light activation. The dark toxicity (toxicity without light activation) of all studied dyes was not detected up to the solubility limit in cell culture medium (10 µM). All studied BODIPY derivatives were predominantly found in adiposomes (lipid droplets) with further lower signals colocalized in either endolysosomal vesicles or the endoplasmic reticulum. A detailed investigation of cell death indicated that the compounds act primarily through the induction of apoptosis. In conclusion, halogenation in the 2,6 position of BODIPY dyes is crucial for the efficient photodynamic activity of these photosensitizers.

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Quantum Chemical Study Aimed at Modeling Efficient Aza-BODIPY NIR Dyes: Molecular and Electronic Structure, Absorption, and Emission Spectra.

Project description:A comprehensive study of the molecular structure of aza-BODIPY and its derivatives, obtained by introduction of one or more substituents, was carried out. We considered the changes in the characteristics of the electronic and geometric structure of the unsubstituted aza-BODIPY introducing the following substituents into the dipyrrin core; phenyl, 2-thiophenyl, 2-furanyl, 3-pyridinyl, 4-pyridinyl, 2-pyridinyl, and ethyl groups. The ground-state geometries of the unsubstituted Aza-BODIPY and 27 derivatives were computed at the PBE/6-31G(d) and CAM-B3LYP/6-31+G(d,p) levels of theory. The time-dependent density-functional theory (TDDFT) together with FC vibronic couplings was used to investigate their absorption and emission spectra.

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Hydrolysis of Formyl Fluoride Catalyzed by Sulfuric Acid and Formic Acid in the Atmosphere.

Project description:Formyl fluoride (HFCO) is an important atmospheric molecule, and its reaction with the OH radical is an important pathway when degradation of HFCO is considered in earth's troposphere. Here, we study the hydrolysis of formyl fluoride (HFCO + H2O) with sulfuric acid (H2SO4) and formic acid (HCOOH) acting as catalysts by utilizing M06-2X, CCSD(T)-F12a, and conventional transitional state theory with Eckart tunneling to explore the atmospheric impact of the above-said hydrolysis reactions. Our calculated results show that H2SO4 has a remarkably catalytic role in the gas-phase hydrolysis of HFCO, as the energy barriers of the HFCO + H2O reaction are reduced from 39.22 and 41.19 to 0.26 and -0.63 kcal/mol with respect to the separate reactants, respectively. In addition, we also find that H2SO4 can significantly accelerate the decomposition of FCH(OH)2 into hydrogen fluoride (HF) and HCOOH. This is because while the barrier height for the unimolecular decomposition of FCH(OH)2 into HF and HCOOH is 31.63 kcal/mol, the barrier height for the FCH(OH)2 + H2SO4 reaction is predicted to be -5.99 kcal/mol with respect to separate reactants. Nevertheless, the comparative relative rate analysis shows that the reaction between HFCO and the OH radical is still the most dominant pathway when the tropospheric degradation of HFCO is taken into account and that the gas-phase hydrolysis of HFCO may only occur with the help of H2SO4 when the atmospheric concentration of OH is about 101 molecules cm-3 or less. Having an understanding from the present study that the gas-phase hydrolysis of HFCO in the presence of H2SO4 has very limited role possibly in the absence of sunlight, we also prefer here to emphasize that the HFCO + H2O + H2SO4 reaction may occur on the surface of secondary organic aerosols for the formation of HCOOH.

| S-EPMC6868600 | biostudies-literature

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