Dyes and Pigments, volume 160, pages 198-207

Halogen-containing BODIPY derivatives for photodynamic therapy

Gorbe Mónica 1
Costero A. M. 2, 3
Martínez-Máñez Ramón 1
Ballesteros Cillero Rafael 2, 3
Ochando L. E. 3, 4
Chulvi K. 2, 3
Gotor Raúl 2, 3
Gil Salvador 2, 3
1
 
Departamento de Química, Universidad Politécnica de Valencia, Valencia, Camino de Vera s/n, 46022, Valencia, Spain
2
 
Departamento de Química Orgánica, Facultad de Química, Universitat de València, Doctor Moliner 50, Burjassot, 46100, Valencia, Spain
3
 
Instituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo Tecnológico (IDM), Universitat Politècnica de Valencia, Universitat de València, Spain
4
 
Departamento de Química Física, Facultad de Química, Universitat de València, Spain
Publication typeJournal Article
Publication date2019-01-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor4.5
ISSN01437208, 18733743
General Chemical Engineering
Process Chemistry and Technology
Abstract
Two iodinated (1 and 2) and two brominated (3 and 4) BODIPY-based photosensitizers are prepared and characterized using slightly modified synthetic procedures previously described. 1–4 present intense absorption bands in the 510–540 nm interval and very weak emissions due to the presence of halogen atoms in their structure. Irradiation of aqueous solutions of 1–4 with visible light (wavelength > 475 nm) induce the generation of singlet oxygen with quantum yields of ca. 0.62–0.66 for the photosensitizers containing iodine atoms (1 and 2) and of ca. 0.16–0.21 for the brominated counterparts (3 and 4). In vitro studies carried out with HeLa, SCC-13 and HaCaT cell lines and the four photosensitizers show marked reductions in cell viability with lower IC50 values for the iodinated derivatives (in the 0.82–2.51 range) than those found for the brominated compounds (in the 0.91–8.26 range) suggesting that these compounds could be used in photodynamic therapy protocols. Subcellular localization studies carried out using confocal microscopy show that photosensitizers accumulated in the endoplasmic reticulum.

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Gorbe M. et al. Halogen-containing BODIPY derivatives for photodynamic therapy // Dyes and Pigments. 2019. Vol. 160. pp. 198-207.
GOST all authors (up to 50) Copy
Gorbe M., Costero A. M., Sancenón F., Martínez-Máñez R., Ballesteros Cillero R., Ochando L. E., Chulvi K., Gotor R., Gil S. Halogen-containing BODIPY derivatives for photodynamic therapy // Dyes and Pigments. 2019. Vol. 160. pp. 198-207.
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RIS Copy
TY - JOUR
DO - 10.1016/j.dyepig.2018.08.007
UR - https://doi.org/10.1016%2Fj.dyepig.2018.08.007
TI - Halogen-containing BODIPY derivatives for photodynamic therapy
T2 - Dyes and Pigments
AU - Gorbe, Mónica
AU - Costero, A. M.
AU - Sancenón, Felix
AU - Martínez-Máñez, Ramón
AU - Ballesteros Cillero, Rafael
AU - Ochando, L. E.
AU - Chulvi, K.
AU - Gotor, Raúl
AU - Gil, Salvador
PY - 2019
DA - 2019/01/01 00:00:00
PB - Elsevier
SP - 198-207
VL - 160
SN - 0143-7208
SN - 1873-3743
ER -
BibTex
Cite this
BibTex Copy
@article{2019_Gorbe,
author = {Mónica Gorbe and A. M. Costero and Felix Sancenón and Ramón Martínez-Máñez and Rafael Ballesteros Cillero and L. E. Ochando and K. Chulvi and Raúl Gotor and Salvador Gil},
title = {Halogen-containing BODIPY derivatives for photodynamic therapy},
journal = {Dyes and Pigments},
year = {2019},
volume = {160},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016%2Fj.dyepig.2018.08.007},
pages = {198--207},
doi = {10.1016/j.dyepig.2018.08.007}
}
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