Synthesis, spectroscopic, and in vitro investigations of 2,6-diiodo-BODIPYs with PDT and bioimaging applications

Journal of Photochemistry and Photobiology. B, Biology
Jaime H GibbsM Graça H Vicente

Abstract

A series of five mono-styryl and their corresponding symmetric di-styryl-2,6-diiodo-BODIPYs containing indolyl, pyrrolyl, thienyl or tri(ethylene glycol)phenyl groups were synthesized using Knoevenagel condensations. The yields for the condensation reactions were improved up to 40% using microwave irradiation (90°C for 1h at 400W) due to lower decomposition of BODIPYs upon prolonged heating. The spectroscopic, structural (including the X-ray of a di-styryl-2,6-diiodo-BODIPY) and in vitro properties of the BODIPYs were investigated. The extension of π-conjugation through the 3,5-dimethyls of the known phototoxic 2,6-diiodo-BODIPY 1 produced bathochromic shifts in the absorption and emission spectra, in the order of 63-125nm for the mono-styryl- and 128-220nm for the di-styryl-BODIPYs in DMSO. The largest red-shifts were observed for the indolyl-containing BODIPYs while the largest fluorescence quantum yields were observed for the tri(ethyleneglycol)phenylstyryl-BODIPYs. Among this series, only the mono-styryl-BODIPYs were phototoxic (IC50=2-15μM at 1.5J/cm(2)), and were observed to localize preferentially in the cell ER and mitochondria. On the other hand, the di-styryl-BODIPYs were found to have low or no phototoxicity (IC50>10...Continue Reading

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Citations

Feb 25, 2017·The Journal of Organic Chemistry·Ning ZhaoM Graça H Vicente
Apr 25, 2018·Lasers in Surgery and Medicine·Jaqueline CarneiroMaria da Graça Henriques Vicente
Oct 7, 2016·New Journal of Chemistry = Nouveau Journal De Chimie·Qianli MengM Graça H Vicente
Jun 23, 2016·Physical Chemistry Chemical Physics : PCCP·Christopher O ObondiFrancis D'Souza
Aug 7, 2017·Beilstein Journal of Organic Chemistry·Ludmila ŠkorpilováZdeněk Wimmer
Mar 19, 2020·Organic & Biomolecular Chemistry·Benjamin F HohlfeldArno Wiehe
Feb 23, 2020·Photochemistry and Photobiology·Ruth Prieto-MonteroVirginia Martínez-Martínez
Sep 29, 2020·Organic & Biomolecular Chemistry·Neliswa Z MhlongoTricia Naicker
Oct 30, 2019·Chemistry : a European Journal·Joanna L DonnellyJonathan D Wilden
Jan 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tyrslai M WilliamsMaria da Graça H Vicente
Jul 3, 2021·International Journal of Molecular Sciences·Ruth Prieto-MonteroVirginia Martínez-Martínez
Apr 18, 2017·Bioconjugate Chemistry·Ning ZhaoM Graça H Vicente
Jul 5, 2018·The Journal of Physical Chemistry. a·Guanyu ZhangM Graça H Vicente
May 19, 2018·The Journal of Organic Chemistry·Andrea SavoldelliM Graça H Vicente

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