Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

Krzemien, Wojciech; Rohlickova, Monika; Machacek, Miloslav; Novakova, Veronika; Piskorz, Jaroslaw; Zimcik, Petr

doi:10.3390/molecules26144194

Open AccessArticle

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

by

Wojciech Krzemien

^1,2,

Monika Rohlickova

²,

Miloslav Machacek

²,

Veronika Novakova

²,

Jaroslaw Piskorz

^1,* and

Petr Zimcik

^2,*

¹

Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland

²

Faculty of Pharmacy in Hradec Kralove, Charles University, Ak. Heyrovskeho 1203, 50003 Hradec Kralove, Czech Republic

^*

Authors to whom correspondence should be addressed.

Molecules 2021, 26(14), 4194; https://doi.org/10.3390/molecules26144194

Submission received: 19 May 2021 / Revised: 30 June 2021 / Accepted: 3 July 2021 / Published: 10 July 2021

(This article belongs to the Special Issue Porphyrinoids and Their Derivatives as Photosensitizers)

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Abstract

The photodynamic properties of a series of non-halogenated, dibrominated and diiodinated BODIPYs with a phthalimido or amino end modification on the phenoxypentyl and phenoxyoctyl linker in the meso position were investigated. Halogen substitution substantially increased the singlet oxygen production based on the heavy atom effect. This increase was accompanied by a higher photodynamic activity against skin melanoma cancer cells SK-MEL-28, with the best compound reaching an EC₅₀ = 0.052 ± 0.01 µM upon light activation. The dark toxicity (toxicity without light activation) of all studied dyes was not detected up to the solubility limit in cell culture medium (10 µM). All studied BODIPY derivatives were predominantly found in adiposomes (lipid droplets) with further lower signals colocalized in either endolysosomal vesicles or the endoplasmic reticulum. A detailed investigation of cell death indicated that the compounds act primarily through the induction of apoptosis. In conclusion, halogenation in the 2,6 position of BODIPY dyes is crucial for the efficient photodynamic activity of these photosensitizers.

Keywords: photodynamic therapy; singlet oxygen; BODIPY; fluorescence; heavy atom effect

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MDPI and ACS Style

Krzemien, W.; Rohlickova, M.; Machacek, M.; Novakova, V.; Piskorz, J.; Zimcik, P. Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters. Molecules 2021, 26, 4194. https://doi.org/10.3390/molecules26144194

AMA Style

Krzemien W, Rohlickova M, Machacek M, Novakova V, Piskorz J, Zimcik P. Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters. Molecules. 2021; 26(14):4194. https://doi.org/10.3390/molecules26144194

Chicago/Turabian Style

Krzemien, Wojciech, Monika Rohlickova, Miloslav Machacek, Veronika Novakova, Jaroslaw Piskorz, and Petr Zimcik. 2021. "Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters" Molecules 26, no. 14: 4194. https://doi.org/10.3390/molecules26144194

APA Style

Krzemien, W., Rohlickova, M., Machacek, M., Novakova, V., Piskorz, J., & Zimcik, P. (2021). Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters. Molecules, 26(14), 4194. https://doi.org/10.3390/molecules26144194

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Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

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