BOPPY-based novel fluorescent dopamine D2 and D3 receptor ligands

Elek, Milica; Dubiel, Mariam; Mayer, Laura; Živković, Aleksandra; Müller, Thomas J. J.; Stark, Holger

doi:10.1016/j.bmcl.2022.128573

Cited by 8 publications

(6 citation statements)

References 33 publications

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“…Owing to the important advantages above, the asymmetrical bisboron-anchoring BOPPY chromophore quickly attracted some attention as advantageous photophysical properties above and promising frameworks for building blocks and functional materials. [47][48][49][50] For example, in 2022, Ono and coworkers 47 reported a new family of BOPPY dimers as flag-hinge chromophores starting from the pre-modified diformyl-2,2'bipyrroles, which manifest good multicolor and circularly polarized emission. Shen and coworkers 48 developed B-O-B bridged BOPPY dimers by reacting 3,5-dimethylpyrrole-2carbaldehyde with 2,3-dihydrazinoquinoxaline, and following boron complex.…”

Section: Synthesis and Properties Of Benzo-fused Boppys From Isoindolesmentioning

confidence: 99%

Recent Advances in Highly Fluorescent Hydrazine-Inserted Pyrrole-Based Diboron-Anchoring Fluorophores: Synthesis and Properties

Sun

Jiao

et al. 2023

Synlett

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Hydrazine inserted pyrrole-based bisboron fluorophores showcasing strong fluorescence in either solution or solid state have attracted wide applications in biomedicine and optoelectronic materials science. The growing demand calls for multiple strategies for generating novel fluorophores to solve the problems of small Stokes shifts and poor solid fluorescence. By changing the frameworks, BOPHY, BOPPY, BOPYPY, BOPAHY and BOAPY has recently been developed as increasingly valuable classes of bisboron fluorophores owing to its tunable structures and promising spectroscopic properties, high photostability and low LUMO energy level and the electron-deficient bisBF2 groups. This review mainly highlights the key synthetic strategies of these hydrazine inserted pyrrole-based bisboron fluorophores BOPHY, BOPPY and BOAPY in our group and their superior properties. Moreover, significant photophysical data of these fluorophores in solution and solid states are also inside the scope of this review. The facile functionalization of these fluorophores’ platforms allows a practically structural modification and generate novel versatile dyes with excellent chemical and photophysical properties. We believe that these fluorophores will hold promise to make an important contribution to various applications.

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Section: Synthesis and Properties Of Benzo-fused Boppys From Isoindolesmentioning

confidence: 99%

Recent Advances in Highly Fluorescent Hydrazine-Inserted Pyrrole-Based Diboron-Anchoring Fluorophores: Synthesis and Properties

Sun

Jiao

et al. 2023

Synlett

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“…Shen 46 developed B− O−B bridged BOPPY dimers by coupling 3,5-dimethylpyrrole-2-carbaldehyde with 2,3-dihydrazinoquinoxaline and found that the two diastereomeric isomers under weak acid could undergo feasible cis−trans interconversion owing to the acidcatalyzed B−N bond cleavage. Stark 47 developed novel BOPPY-based fluorescent dopamine D2 and D3 receptor ligands, which demonstrate relatively large Stokes shifts and provide versatile possibility for amine coupling. Despite the abovementioned advantages, the emission wavelength of the parent BOPPY backbone 44 (397 and 418 nm in toluene) is shorter than that of the parent BODIPY backbone (505 nm in toluene), 48 which dramatically restricts its application in the biological process.…”

Section: ■ Introductionmentioning

confidence: 99%

Aromatic-Ring-Fused BOPPY Fluorophores: Synthesis, Spectral, Redox Properties, and Bioimaging Application

Sun

Fang

et al. 2022

Inorg. Chem.

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Tetracoordinated organoboron dyes exhibiting strong fluorescence in either solution or the solid state are currently receiving much attraction in view of their photovoltaic, optoelectronic, and biological applications. Herein, a series of aromatic-ring-fused BOPPY dyes have been developed by one-pot condensation of formylated isoindoles or indoles and pyridinylhydrazine followed by subsequent borylation coordination. The facile synthesis provides excellent diversity of these unsymmetrical α-benzoand β-benzothiophene-fused BOPPY dyes with intriguing photophysical properties owing to their rigid and planar structure and extended πconjugation while containing a reactive site. They display intense green to orange fluorescence in solution and red-to-near-infrared emission in the solid state, with high fluorescence quantum yields up to 92 and 21%, respectively, relatively large Stokes shifts, and excellent photostability. Furthermore, two representative benzofused BOPPY probes with morpholine or benzenesulfonamide groups were developed and used to selectively "light up" the subcellular organelles such as lysosomes and endoplasmic reticulum under ultralow concentration, respectively.

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“…Since both dyes are hydrophilic, they are less prone to interact with cell membranes than, for example, BODIPY fluorescent dyes, resulting in reduced nonspecific binding [36] . Compared to previously published fluorescent ligands for D 2 ‐like receptors, [31,37,38] our antagonistic ligand scaffold together with the more hydrophilic 5‐TAMRA and DY549 dyes combines better solubility properties and is not susceptible to receptor internalization when applied to whole cells. In addition, TAMRA ligands have already repeatedly demonstrated their suitability in NanoBRET assays, which opens up another possible application for our fluorescent ligands [13,22,39] …”

Section: Resultsmentioning

confidence: 99%

Fluorescent Tools for the Imaging of Dopamine D₂‐Like Receptors**

Nagl,

Mönnich,

Rosier

et al. 2023

ChemBioChem

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The family of dopamine D2‐like receptors represents an interesting target for a variety of neurological diseases, e. g. Parkinson's disease (PD), addiction, or schizophrenia. In this study we describe the synthesis of a new set of fluorescent ligands as tools for visualization of dopamine D2‐like receptors. Pharmacological characterization in radioligand binding studies identified UR‐MN212 (20) as a high‐affinity ligand for D2‐like receptors (pKi (D2longR)=8.24, pKi (D3R)=8.58, pKi (D4R)=7.78) with decent selectivity towards D1‐like receptors. Compound 20 is a neutral antagonist in a Go1 activation assay at the D2longR, D3R, and D4R, which is an important feature for studies using whole cells. The neutral antagonist 20, equipped with a 5‐TAMRA dye, displayed rapid association to the D2longR in binding studies using confocal microscopy demonstrating its suitability for fluorescence microscopy. Furthermore, in molecular brightness studies, the ligand's binding affinity could be determined in a single‐digit nanomolar range that was in good agreement with radioligand binding data. Therefore, the fluorescent compound can be used for quantitative characterization of native D2‐like receptors in a broad variety of experimental setups.

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BOPPY-based novel fluorescent dopamine D2 and D3 receptor ligands

Cited by 8 publications

References 33 publications

Recent Advances in Highly Fluorescent Hydrazine-Inserted Pyrrole-Based Diboron-Anchoring Fluorophores: Synthesis and Properties

Recent Advances in Highly Fluorescent Hydrazine-Inserted Pyrrole-Based Diboron-Anchoring Fluorophores: Synthesis and Properties

Aromatic-Ring-Fused BOPPY Fluorophores: Synthesis, Spectral, Redox Properties, and Bioimaging Application

Fluorescent Tools for the Imaging of Dopamine D₂‐Like Receptors**

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BOPPY-based novel fluorescent dopamine D2 and D3 receptor ligands

Cited by 8 publications

References 33 publications

Recent Advances in Highly Fluorescent Hydrazine-Inserted Pyrrole-Based Diboron-Anchoring Fluorophores: Synthesis and Properties

Recent Advances in Highly Fluorescent Hydrazine-Inserted Pyrrole-Based Diboron-Anchoring Fluorophores: Synthesis and Properties

Aromatic-Ring-Fused BOPPY Fluorophores: Synthesis, Spectral, Redox Properties, and Bioimaging Application

Fluorescent Tools for the Imaging of Dopamine D2‐Like Receptors**

Contact Info

Product

Resources

About

Fluorescent Tools for the Imaging of Dopamine D₂‐Like Receptors**