Visualization of tyrosinase activity in melanoma cells by a BODIPY-based fluorescent probe

Kim, Tae Il; Park, Jihye; Park, Seonhwa; Choi, Yongdoo; Kim, Youngmi

doi:10.1039/c1cc15061h

Cited by 89 publications

(59 citation statements)

References 18 publications

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“…Also, solubility and electron‐withdrawing/electron‐donor characteristics of the compounds can also be regulated as needed. Recently, the tetradentate salen/salan ligand and two fluorine or phenyl atoms chelated tetra‐coordinate organoboron complexes have been significantly developed and have undergone widespread application in the fields of materials, molecular machines, OLEDs, probes solar energy collectors, organic electronics and photonics, bioimaging, photodynamic therapy, and digital design, etc ., is performed by chemists, physicists, engineers, and material scientist. For these applications, tetra‐coordinate organoboron complexes have received considerable attention due to the generally more stable than other organometallic derivatives in the presence of a weak coordinative B→N and a strong covalent B–O bond .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties

Kılıç

Koyuncu

Durgun

et al. 2017

Chemistry & Biodiversity

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The synthesis, spectroscopic properties, and in vitro cytotoxicity activity of a series of various salen-based triboron complexes have been designed and prepared from hemi-salen (L 1 H 3 -L 4 H 3 ) ligands and BF 3 ÁEt 2 O or BPh 3 under simple reaction conditions. The hemi-salen (L 1 H 3 -L 4 H 3 ) ligands and their BF 2 or BPh 2 chelating triboron complexes were characterized by means of NMR ( 1 H, 13 C, 19 F, and 11 B) spectra, FT-IR spectra, UV/VIS spectra, fluorescence spectra, mass spectra, melting point, as well as elemental analysis. The triboron [L (1 -4) (BF 2 ) 3 ] and [L (1 -4) (BPh 2 ) 3 ] complexes were investigated for their absorption and emission properties, and these complexes are also good chelates towards boron(III) fragments such as BF 2 or BPh 2 quantum yield in solution reaching up to 38%. The hemisalen (L 1 H 3 -L 4 H 3 ) ligands and their BF 2 or BPh 2 chelating triboron complexes were tested for the in vitro anticancer activity against various cancer and normal cells (HeLa, DLD-1, ECC-1, PC-3, PNT-1A, and CRL-4010), and it was found that the cell viability of cancer cells was decreased while most of the healthy cells could still be viable. Also, the cytotoxicity studies showed that anticancer activity of hemi-salenligands showing the strongest cytotoxic effect in PC-3 cells were found to exhibit anticancer activity with apoptosis by increasing the level of ROS in the PC-3 cells.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties

Kılıç

Koyuncu

Durgun

et al. 2017

Chemistry & Biodiversity

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“…Among the variously developed TR sensors, fluorescence-based assays are promising methods due to their high sensitivity and noninvasive imaging. 1,[3][4][5] However, the fluorescent probes based on the fluorescence quenching (turn-off ) or enhancing (turn-on) effects at a certain wavelength generally suffer from the unavoidable disturbance induced by intensity fluctuations ascribed to the instrumental or environmental factors. 6,7 Very recently, the ratiometric TR sensing mechanisms by measuring the relative fluorescence varies at two wavelengths of a fluorescent probe, coupling with the TR-catalyzed oxidation of TR substrate, dopamine, have been expected to overcome the above-mentioned concern.…”

mentioning

confidence: 99%

Two-Photon Semiconducting Polymer Dots with Dual-Emission for Ratiometric Fluorescent Sensing and Bioimaging of Tyrosinase Activity

et al. 2016

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Semiconducting polymer dots (Pdots) with one-, two-photon excitation and dual-emission have been synthesized by coprecipitation of two conjugated polymers including poly(9,9-dioctylfluorenyl-2,7-diyl) (PFO) and poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-(1-cyanovinylene-1,4-phenylene)] (CN-PPV) and have been further functionalized with l-tyrosine methyl ester (Tyr-OMe) via electrostatic assembly for ratiometric fluorescent sensing and bioimaging of tyrosinase activity. Tyrosinase-catalyzed oxidation of Tyr-OMe effectively modulate the dual-emission fluorescence of PFO/CN-PPV@Tyr-OMe Pdots from orange to blue through a selective photoinduced electron transfer (PET) process. A two-photon ratiometric sensor at almost zero-background interference and bioimaging of tyrosinase activity have been demonstrated, suggesting the potential biomedical applications of the prepared functionalized Pdots.

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“…58 We can find in the literature NIR BODIPY-based fluorescent compounds capable to penetrate the cell and localize in the cytoplasm 59 or organelles such as mitochondria and endoplasmic reticulum 60,61 also there are reports of fluorescent probes for specific molecules such as enzymes. 62 Fluorescent molecular rotors of Boron compounds derived from Schiff bases has been reported as well, as favorable molecules to penetrate the cell membrane and stain the cytoplasm. These compounds demonstrate the quantum yield rise when solvent viscosity increases as well, property that is extremely functional in viscosity studies on cellular scale.…”

Section: Fluorescent Bioimaging By Luminescent Organoboron Materialsmentioning

confidence: 99%

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Muñoz‐Flores

Molina‐Paredes

Lara‐Cerón

et al. 2018

IJAMB

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The increasing interest in the luminescent boron materials is due to their potential application in diverse areas such as solar cells, optoelectronic devices, and biological imaging materials. Continuous search for the compounds with better properties, luminescent organoboron materials have been gaining more importance, especially in the development of new technologies and novel techniques for bioimaging, which is a powerful tool to analyze the cellular organelles with important value into the cell biology and medical research. Synthesis, properties, and applications of luminescent boron compounds and their application in bioimaging are reviewed.

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Visualization of tyrosinase activity in melanoma cells by a BODIPY-based fluorescent probe

Cited by 89 publications

References 18 publications

Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties

Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties

Two-Photon Semiconducting Polymer Dots with Dual-Emission for Ratiometric Fluorescent Sensing and Bioimaging of Tyrosinase Activity

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

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