Synthesis, characterization, photophysical properties of new fluorescent boron Schiff bases (BOSCHIBAs) and their application as cytoplasm staining dyes in vitro

Corona-López, María M.; Jiménez-Pérez, Vı́ctor M.; Chan-Navarro, Rodrigo; Ibarra-Rodríguez, Marisol; Dias, H. V. Rasika; Chávez‐Reyes, Arturo; Muñoz‐Flores, Blanca M.

doi:10.1016/j.jorganchem.2017.10.003

Cited by 19 publications

(12 citation statements)

References 35 publications

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“…Recently,w eh ave been active in the design and synthesis of new fluorescent organoboron [21][22][23] and diorganotin derivatives bearing Schiff-base ligands. [24,25] Moreover,w eh ave demonstrated that fluorescent organotin derivatives I and J (Scheme 3) can be used as cytoplasm markersf or in vitro cell imaging.…”

Section: Introductionmentioning

confidence: 99%

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Muñoz‐Flores

Cabrera‐González

Viñas

et al. 2018

Chemistry A European J

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Within the cell nucleus, in the nucleoli, ribosomal RNAs are synthesized and participate in several biological processes. To better understand nucleoli-related processes, their visualization is often required, for which specific markers are needed. Herein, we report the design of novel fluorescent organotin compounds derived from 4-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide and their cytoplasm and nucleoli staining of B16F10 cells in vitro. Tin compounds bearing an aliphatic carbon chain (-C H ) and an electron-donating group (-OH) were prepared, and the latter could be derivatized to bear the boron cluster anions [B H ] and [3,3'-Co(1,2-C B H ) ] (COSAN). All of the conjugates have been fully characterized and their luminescence properties have been assessed. In general, they show good quantum yields in solution (24-49 %), those for the COSAN derivatives being lower. Remarkably, the linking of [B H ] and COSAN to the complexes made them more soluble, without being detrimental to their luminescence properties. Living B16F10 cells were treated with all of the compounds to determine their fluorescence staining properties; the compounds bearing the aliphatic chain showed a reduced staining capacity due to the formation of aggregates. Notably, the complexes bearing different boron clusters showed different staining effects; those bearing [B H ] showed extraordinary staining of the nucleoli and cytoplasm, whereas those bearing COSAN were only detected in the cytoplasm. The remarkable fluorescence staining properties shown by these organotin compounds make them excellent candidates for fluorescence bioimaging in vitro.

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Section: Introductionmentioning

confidence: 99%

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Muñoz‐Flores

Cabrera‐González

Viñas

et al. 2018

Chemistry A European J

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“…Complexes 1 – 5 are soluble in ethyl acetate, chloroform, and CH 2 Cl 2 . The microwave‐assisted synthesis, resulted to be ten times faster and cheaper than the traditional solution via …”

Section: Resultsmentioning

confidence: 99%

Fluorescent boron Schiff bases dyes for staining silk fibroin: Green synthesis, structural characterization, DFT, and photophysical properties

Molina‐Paredes

Jiménez-Pérez

Lara‐Cerón

et al. 2018

Applied Organom Chemis

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Five novel organoboron complexes were synthesized in just 15 min via microware irradiation, by one pot multicomponent reactions between diverse aryl aldehydes with benzoylhydrazide, or 4-nitrobenzoylhidrazine and diphenyl boronic acid, in a 1:1:1 ratio in benzene. The products were characterized by 1 H, 13 C, 11 B NMR, UV, IR, spectroscopy and high-resolution mass spectrometry (HRMS). The molecular structure was also determined by singlecrystal X-ray diffraction for two complexes, which showed the tetra-coordination of the boron atoms giving rise to distorted tetrahedral molecular geometry with a strong intermolecular C-H···π interactions. In spite of the low quantum yields exhibited by the series in solution, some complexes stained uniformly the silk fibroins emitting enough fluorescence to allow its characterization by confocal microscopy. Boron as chelate center of the five complexes resulted not to be toxic for B16F10 cells, these compounds are appropriate for their used in medical applications.

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“…Solvents were used without further purification. The ligands L1‐L4 were prepared accorded to the method reported as well as compound 1 . Melting points were performed on an Electrothermal Mel‐Temp apparatus and are uncorrected.…”

Section: Methodsmentioning

confidence: 99%

“…However, the compound ( I ) shows the molecular rotor property with the ability to increase the luminescence in a viscous medium . BOSCHIBAs ( II ‐ IV ) were designed for the same purpose where the compounds showed high stability in aqueous solution and UV radiation, with low cytotoxicity and cytoplasmic staining dyes in B16F10 cells (from 0.1 to 2.5 mg/mL) . In order to contribute in the fluorescent imaging technologies, we have been interested in the design and synthesis of Boron Schiff bases as fluorescent dyes for bioimaging.…”

Section: Introductionmentioning

confidence: 99%

Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

Ibarra-Rodríguez

Muñoz‐Flores

Gómez-Treviño

et al. 2019

Applied Organom Chemis

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The fluorescence imaging technologies are becoming the most powerful and noninvasive diagnostic tools in cellular biology and modern medicine where abnormal cell arrangements are associated with diseases. Thus, these techniques require new fluorescent dyes with excellent chemical, physical, and photophysical properties. A series of four new Boron Schiff bases (1–4) has been prepared by condensation between phenylboronic acid with the corresponding ligand. The compounds were characterized by NMR (1H, 13C, and 11B), UV/vis, fluorescence spectroscopy, and high‐resolution mass spectrometry. The crystal structures of three compounds showed tetracoordinated Boron atoms with semiplanar skeleton ligands. Interesting organoboron response to viscosity on their fluorescence (Φ: more than 3‐fold). Additionally, compounds 1 and 2 were found to serve as a fluorescent dye for cell imaging (B16F10, CaCo, and A‐431 cells) since it has the capability to rapidly accumulate within the cells and gave bright green fluorescence, it showed low cytotoxicity activity and high photostability in solution. Additionally, the compounds have also been investigated using DFT.

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Synthesis, characterization, photophysical properties of new fluorescent boron Schiff bases (BOSCHIBAs) and their application as cytoplasm staining dyes in vitro

Cited by 19 publications

References 35 publications

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Fluorescent boron Schiff bases dyes for staining silk fibroin: Green synthesis, structural characterization, DFT, and photophysical properties

Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

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