Enhanced Hypsochromic Shifts, Quantum Yield, and π–π Interactions in a <i>meso</i>,β-Heteroaryl-Fused BODIPY

Zhao, Ning; Xuan, Sunting; Fronczek, Frank R.; Vicente, M. Graça H.

doi:10.1021/acs.joc.6b02981

Cited by 29 publications

(15 citation statements)

References 49 publications

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“…The optical properties of FS (λ max,abs = 1026 nm, λ max,em = 1065 nm in CH 2 Cl 2 ; ε = 5.09 × 10 5 M –1 cm –1 , Φ = 0.305% in DMSO) have no obvious change in comparison with Flav7 (Figure a), indicating a negligible PET process due to the weak electron-donating capability of the thio substituent . The slightly blue shift of FS in fluorescence emission spectra (λ max,em = 1065 nm in CH 2 Cl 2 ) may be induced by the increase in molecular rigidity after introducing the functional substituent …”

Section: Resultsmentioning

confidence: 96%

Polypeptide-Conjugated Second Near-Infrared Organic Fluorophore for Image-Guided Photothermal Therapy

et al. 2019

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Image-guided photothermal therapy (PTT) is an attractive strategy to improve the diagnosis accuracy and treatment outcomes by monitoring the accumulation of photothermal agents in tumors in real-time and determining the best treatment window. Taking advantage of the superior imaging quality of NIR-II fluorescence imaging and remote-controllable phototherapy modality of PTT, we developed a facile macromolecular fluorophore (PF) by conjugating a small-molecule NIR-II fluorophore (Flav7) with an amphiphilic polypeptide. The PF can form uniform micelles in aqueous solution, which exhibit a slight negative charge. In vitro experimental results showed that the PF nanoparticles showed satisfactory photophysical properties, prominent photothermal conversion efficiency (42.3%), excellent photothermal stability, negligible cytotoxicity, and photothermal toxicity. Meanwhile, the PF can visualize and feature the tumors by NIR-II fluorescence imaging owing to prolonged blood circulation time and enhanced accumulation in tumors. Moreover, in vivo studies revealed that the PF nanoparticles achieved an excellent photothermal ablation effect on tumors with a low dose of NIR-II dye and light irradiation, and the process can be traced by NIR fluorescence imaging.

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Section: Resultsmentioning

confidence: 96%

Polypeptide-Conjugated Second Near-Infrared Organic Fluorophore for Image-Guided Photothermal Therapy

et al. 2019

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“…Energy transfer efficiencies in the analyte-free milk solutions (to which small amounts of fluorophores 11–13 were added) were calculated according to Equation 1, and the results are summarized in Table 1. These results show that the energy transfer efficiencies were highest in the presence of fluorophore acceptor 11 , which is a consequence of the high quantum yield of that fluorophore (0.96 in tetrahydrofuran) (Zhang et al 2016; Zhao et al 2017), its electrostatic potential surface which is strongly complementary to that of the aromatic analytes (see ESI for more details), and its demonstrated ability to bind in or near the γ-cyclodextrin cavity and facilitate proximity-induced energy transfer (Milles et al 2013). In contrast, the structure of fluorophore 12 makes it less able to penetrate the cyclodextrin cavity (both because of the large steric size as well as its central twisted biphenyl axis) (Zhao et al 2010), and the quantum yield of fluorophore 13 is lower than that of fluorophore 11 (Rodionova et al 2008).…”

Section: Resultsmentioning

confidence: 77%

Cyclodextrin-Promoted Fluorescence Detection of Aromatic Toxicants and Toxicant Metabolites in Commercial Milk Products

et al. 2018

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The detection of polycyclic aromatic hydrocarbons (PAHs) and their metabolites in food and in agricultural sources is an important research objective due to the PAHs’ known persistence, carcinogenicity, and toxicity. PAHs have been found in the milk of lactating cows, and in the leaves and stems of plants grown in PAH-contaminated areas, thereby making their way into both cow milk and plant milk alternatives. Reported herein is the rapid, sensitive, and selective detection of 10 PAHs and PAH metabolites in a variety of cow milks and plant milk alternatives using fluorescence energy transfer from the PAH to a high quantum yield fluorophore, combined with subsequent array-based statistical analyses of the fluorescence emission signals. This system operates with high sensitivity (low micromolar detection limits), selectivity (100% differentiation even between structurally similar analytes), and general applicability (for both unmodified lipophilic PAHs and highly polar oxidized PAH metabolites, as well as for different cow and plant milk samples). These promising results show significant potential to be translated into solid-state devices for the rapid, sensitive, and selective detection of PAHs and their metabolites in complex, commercial food products.

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“…A hypsochromic shift in absorption spectrum and an enhanced Stokes shift of BODIPY dye 11 in comparison with BODIPY 1 ( Table 1 ) can hardly be explained by the chlorine substitution in coumarin ring [ 56 ]; however, similar effects were observed in a fused planar BODIPY [ 57 ]. Unusual spectral properties of BODIPY dye 11 make this compound interesting for further study.…”

Section: Resultsmentioning

confidence: 99%

Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift

Raskolupova

Popova²,

Zakharova

et al. 2021

Molecules

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BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials, and molecular probes. At the same time, BODIPY dyes have small or moderate Stokes shifts like most other fluorophores. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. The new boron containing BODIPY dye was designed and synthesized. We succeeded to perform an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. This BODIPY dye was equipped with linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. BODIPY residue equipped with a suitable targeting protein core can be used as a suitable imaging probe and agent for Boron Neutron Capture Therapy (BNCT). As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal constructions. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA were labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis, and fluorescent emission spectra. Cytotoxicity of the resulting conjugate was investigated. This study is the basis for a novel BODIPY dye-albumin theranostic for BNCT. The results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.

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Enhanced Hypsochromic Shifts, Quantum Yield, and π–π Interactions in a meso,β-Heteroaryl-Fused BODIPY

Cited by 29 publications

References 49 publications

Polypeptide-Conjugated Second Near-Infrared Organic Fluorophore for Image-Guided Photothermal Therapy

Polypeptide-Conjugated Second Near-Infrared Organic Fluorophore for Image-Guided Photothermal Therapy

Cyclodextrin-Promoted Fluorescence Detection of Aromatic Toxicants and Toxicant Metabolites in Commercial Milk Products

Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift

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