Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging
Por:
Obregon-Mendoza, Marco A., Arias-Olguin, Imilla I., Mirian Estevez-Carmona, M., Meza-Morales, William, Alvarez-Ricardo, Yair, Toscano, Ruben A., Arenas-Huertero, Francisco, CASSANI, JULIA, Enriquez, Raul G.
Publicada:
1 jul 2020
Resumen:
Curcumin, the most important secondary metabolite isolated fromCurcuma
longa, is known for its numerous purported therapeutic properties and as
a natural dye. Herein, based on curcumin's intrinsic fluorescence, a
search for improved curcumin-based fluorophores was conducted. Within
the set of semi-synthetic curcumin derivatives i.e. mono (1), di (2),
tri (3), tetra (4) benzylated and dibenzyl-fluoroborate (5), the
fluorescence properties of2and5in solution outstood with a two-fold
quantum yield compared to curcumin. Furthermore, all benzylated
derivatives showed a favorable minimal cytotoxic activity upon screening
at 25 mu M against human cancer and non-tumoral COS-7 cell lines, with a
reduction of its cytotoxic effect related to the degree of substitution.
Fluorophores2and5are versatile bioimaging tools, as revealed by Confocal
Fluorescence Microscopy (CFM), and showed permeation of living cell
membranes of astrocytes and astrocytomas. When2is excited with a 405-
(blue) or 543-nm (green) laser, it is possible to exclusively and
intensively visualize the nucleus. However, the fluorescence emission
fades as the laser wavelength moves towards the red region. In
comparison,5allows selective visualization of cytoplasm when a 560-nm
laser is used, showing emission in the NIR region, while it is possible
to exclusively observe the nucleus at the blue region with a 405-nm
laser.
Filiaciones:
Obregon-Mendoza, Marco A.:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
Arias-Olguin, Imilla I.:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
Mirian Estevez-Carmona, M.:
Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Wilfrido Massieu SN, Ciudad De Mexico 07738, Mexico
Meza-Morales, William:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
Alvarez-Ricardo, Yair:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
Toscano, Ruben A.:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
Arenas-Huertero, Francisco:
Hosp Infantil Mexico Dr Federico Gomez, Lab Invest Patol Expt, Ciudad De Mexico 06720, Mexico
CASSANI, JULIA:
Univ Autonoma Metropolitana, Dept Sistemas Biol, Unidad Xochimilco, Ciudad De Mexico 04960, Mexico
Enriquez, Raul G.:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
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