TY - JOUR
T1 - Non-cytotoxic dibenzyl and difluoroborate curcuminoid fluorophores allow visualization of nucleus or cytoplasm in bioimaging
AU - Obregón-Mendoza, Marco A.
AU - Arias-Olguín, Imilla I.
AU - Estévez-Carmona, M. Mirian
AU - Meza-Morales, William
AU - Alvarez-Ricardo, Yair
AU - Toscano, Rubén A.
AU - Arenas-Huertero, Francisco
AU - Cassani, Julia
AU - Enríquez, Raúl G.
N1 - Publisher Copyright:
© 2020 by the authors.
PY - 2020/7
Y1 - 2020/7
N2 - Curcumin, the most important secondary metabolite isolated from Curcuma 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 of 2 and 5 in 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 μM against human cancer and non-tumoral COS-7 cell lines, with a reduction of its cytotoxic effect related to the degree of substitution. Fluorophores 2 and 5 are versatile bioimaging tools, as revealed by Confocal Fluorescence Microscopy (CFM), and showed permeation of living cell membranes of astrocytes and astrocytomas. When 2 is 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, 5 allows 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.
AB - Curcumin, the most important secondary metabolite isolated from Curcuma 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 of 2 and 5 in 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 μM against human cancer and non-tumoral COS-7 cell lines, with a reduction of its cytotoxic effect related to the degree of substitution. Fluorophores 2 and 5 are versatile bioimaging tools, as revealed by Confocal Fluorescence Microscopy (CFM), and showed permeation of living cell membranes of astrocytes and astrocytomas. When 2 is 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, 5 allows 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.
KW - Curcumin-based fluorescent probes
KW - Curcuminoid fluorophores
KW - Fluorescent probes
KW - Staining live cells
UR - http://www.scopus.com/inward/record.url?scp=85088155914&partnerID=8YFLogxK
U2 - 10.3390/molecules25143205
DO - 10.3390/molecules25143205
M3 - Artículo
C2 - 32674349
AN - SCOPUS:85088155914
SN - 1420-3049
VL - 25
JO - Molecules
JF - Molecules
IS - 14
M1 - 3205
ER -