Novel 17 alpha-Etinylestradiol-Substituted BODIPY Dyes: Synthesis, Photophysical Properties and Fluorescence Imaging Studies in Breast Cancer Cell Lines

Date

2018-03-22

Author

Kazan, Hasan H.
Ozcan, Emrah
Ecik, Esra T.
Cosut, Bunyemin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

72
views

0
downloads

Novel 17 alpha-Etinylestradiol-substituted 4,4-difluoro-4-borata-3a, 4a-diaza-s-indacene (BODIPY) dyes were prepared as fluorescent imaging probes. The identities of newly synthesized dyes were fully characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and H-1 and C-13 nuclear magnetic resonance (NMR) spectroscopy. The photophysical properties (molar extinction coefficient, fluorescence lifetime and fluorescence quantum yield) of the compounds were investigated by means of absorption and fluorescence spectroscopies in dilute ethanol solutions. We were also interested in the live cell imaging studies of the 17 alpha-etinylestradiol-linked BODIPYs, by particularly concerning their ability to monitoring breast cancer cell lines. These studies showed that one of the novel 17 alpha-etinylestradiol-substituted BODIPY dyes was able to distinguish breast cancer subtypes. This is the first study sub-categorizing breast cancer via fluorescent-tagged estrogen analog, which is critical in terms of improving the molecular diagnostics and eliminating the drawbacks of available methods. These studies are very selective up to date for a BODIPY-based fluorescent label and define a pivotal biological importance of BODIPY as a building block in live cell imaging studies.

Subject Keywords

17 alpha-etinylestradiol, Borondipyrromethenes, Estrogen receptor, Fluorescence, Live cell imaging

URI

https://hdl.handle.net/11511/67472

Journal

CHEMISTRYSELECT

DOI

https://doi.org/10.1002/slct.201800030

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Azaindole-BODIPYs: Synthesis, fluorescent recognition of hydrogen sulfate anion and biological evaluation Kesan, Gurkan; Topaloglu, Burcu; Ozcan, Emrah; Kazan, Hasan Huseyin; TANRIVERDİ EÇİK, ESRA; ŞENKUYTU, ELİF; ŞENGÜL, İBRAHİM FAZIL; KANDEMİR, HAKAN; ÇOŞUT, BÜNYEMİN (2019-04-15) The synthesized and sensing capability of two novel azaindole substituted mono and distyryl BODIPY dyes against bisulfate anion were reported. Structural characterizations of the targeted compounds were conducted by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, H-1 and C-13 NMRspectroscopies. Photophysical properties of the azaindole substituted BODIPY compounds were investigated employing absorption and fluorescence spectroscopies in acetonitrile solution. It was found...
Photovoltaic Properties of Poly(Triphenylamine-Thiazolo[5,4-d] Thiazole) Copolymer Dye in Bulk-Hetorojunction Organic Solar Cells Olgun, Ugursoy; Gulfen, Mustafa; HIZALAN, Gonul; Çırpan, Ali; Toppare, Levent Kamil (2017-04-01) In this study, the photovoltaic properties of poly(triphenylamine-thiazolo[5,4-d]thiazole) alternating copolymer dye in bulk heterojunction polymer solar cells were examined. The copolymer is a red colored dye material with high thermal stability, good solubility and low-band gap energy. The band gap energy of the polymer was determined as 1.36 eV. The conductivity of the polymer thin film was measured as 1.5x10(-5) S/cm. The polymer solar cells were fabricated using the different ratios of the blends of th...
Production of core-shell type conducting FTO/TiO2 photoanode for dye sensitized solar cells Icli, Kerem Cagatay; Yavuz, Halil Ibrahim; Özenbaş, Ahmet Macit (2014-02-01) Core-shell type photoanode composed of electrically conducting fluorine doped tin dioxide (FTO) matrix and TiO2 shell layer was prepared and applied in dye sensitized solar cells. Effects of fluorine doping on tin dioxide based cells and precursor material on shell layer were investigated. Fluorine doped tin dioxide nanoparticles were synthesized under hydrothermal conditions and resistivity value down to 17 Omega cm was achieved. Cells constructed from FTO nanoparticles show enhanced performance compared t...
Optical characterization of Ga2SeS layered crystals by transmission, reflection and ellipsometry IŞIK, MEHMET; Hasanlı, Nızamı (2015-07-10) Optical properties of Ga2SeS crystals grown by Bridgman method were investigated by transmission, reflection and ellipsometry measurements. Analysis of the transmission and reflection measurements performed in the wavelength range of 400-1100 nm at room temperature indicated the presence of indirect and direct transitions with 2.28 eV and 2.38 eV band gap energies. Ellipsometry measurements were carried out in the 1.2-6.0 eV spectral region to get information about optical constants, real and imaginary part...
Induction thermal plasma synthesis of Mg2Ni nanoparticles Aktekin, Burak; ÇAKMAK, GÜLHAN; Öztürk, Tayfur (2014-06-15) A study was carried out into possibility of thermal plasma synthesis of Mg2Ni nanoparticles. Both prealloyed powders and elemental powders were used as precursors in an inductively coupled thermal plasma incorporating two injection probes located axially in the reactor one from the top and the other from the bottom. The study has shown that the use of prealloyed Mg2Ni as precursor leads to its disintegration in the plasma condensing into separate phases and therefore was not suitable for the synthesis of Mg...

Citation Formats

H. H. Kazan, E. Ozcan, E. T. Ecik, and B. Cosut, “Novel 17 alpha-Etinylestradiol-Substituted BODIPY Dyes: Synthesis, Photophysical Properties and Fluorescence Imaging Studies in Breast Cancer Cell Lines,” CHEMISTRYSELECT, pp. 2962–2967, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/67472.