Dyes and Pigments, volume 178, pages 108322
Boron-dipyrromethene derivatives bearing N-alkyl phthalimide and amine substituents of potential application in the photoinactivation of bacteria
Piskorz Jaroslaw
1
,
Dlugaszewska Jolanta
2
,
Porolnik Weronika
1
,
Teubert Anna
3
,
Mielcarek Jadwiga
1
1
Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6,60-780 Poznan,Poland
|
2
Department of Genetics and Pharmaceutical Microbiology, Poznan University of Medical Sciences, Swiecickiego 4, 60-781 Poznan, Poland
|
3
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland.
|
Publication type: Journal Article
Publication date: 2020-07-01
Journal:
Dyes and Pigments
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.5
ISSN: 01437208, 18733743
General Chemical Engineering
Process Chemistry and Technology
Abstract
Novel boron-dipyrromethene derivatives with N-alkyl phthalimide and amine substituents, including iodinated derivative, were synthesized and characterized using UV–Vis spectrophotometry, mass spectrometry (HRMS) and NMR spectroscopy. Non-iodinated analogs revealed high emission properties with fluorescence quantum yields (Φ F ) between 0.48 and 0.58. But singlet oxygen generation quantum yields (Φ Δ ) were low with values in the range of 0.01–0.06. Iodinated derivative revealed a strong heavy atom effect resulted in the red-shifted absorption and emission bands, fluorescence quenching with Φ F values of about 0.02, but increased singlet oxygen generation abilities with excellent Φ Δ values of 0.97 and 0.85 in methanol and ethanol, respectively. In vitro photodynamic inactivation activity was evaluated on Gram-positive cocci of Staphylococcus aureus and Gram-negative rods of Escherichia coli. Novel BODIPY derivatives showed promising inactivation efficiency on S. aureus , with the highest activity for iodinated derivative, which reduced the number of bacteria by 3.6 logs 10 at low 0.5 μM concentration. However, none of the tested derivatives showed a satisfactory ability to eradicate E. coli . Only non-iodinated derivative with amine substituent, at high concentrations, showed some significant activity with log 10 reduction values of 2.0 and 1.1 at 500 and 50 μM, respectively. Nevertheless, the presented approach enabled to obtain novel BODIPY derivatives with promising photoinactivation activity and properties such as fluorescence and singlet oxygen generation efficacy, easy to modify by the heavy atom substitution. Also, peripheral phthalimide or amine groups can be used for further structural modifications. • Novel BODIPYs with N-alkyl phthalimide and amine substituents were synthesized. • Strong heavy atom effect for iodinated derivative was found. • Tested derivatives showed promising photoinactivation efficiency on S. aureus .
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Piskorz J. et al. Boron-dipyrromethene derivatives bearing N-alkyl phthalimide and amine substituents of potential application in the photoinactivation of bacteria // Dyes and Pigments. 2020. Vol. 178. p. 108322.
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Piskorz J., Dlugaszewska J., Porolnik W., Teubert A., Mielcarek J. Boron-dipyrromethene derivatives bearing N-alkyl phthalimide and amine substituents of potential application in the photoinactivation of bacteria // Dyes and Pigments. 2020. Vol. 178. p. 108322.
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TY - JOUR
DO - 10.1016/j.dyepig.2020.108322
UR - https://doi.org/10.1016%2Fj.dyepig.2020.108322
TI - Boron-dipyrromethene derivatives bearing N-alkyl phthalimide and amine substituents of potential application in the photoinactivation of bacteria
T2 - Dyes and Pigments
AU - Piskorz, Jaroslaw
AU - Dlugaszewska, Jolanta
AU - Porolnik, Weronika
AU - Teubert, Anna
AU - Mielcarek, Jadwiga
PY - 2020
DA - 2020/07/01 00:00:00
PB - Elsevier
SP - 108322
VL - 178
SN - 0143-7208
SN - 1873-3743
ER -
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@article{2020_Piskorz,
author = {Jaroslaw Piskorz and Jolanta Dlugaszewska and Weronika Porolnik and Anna Teubert and Jadwiga Mielcarek},
title = {Boron-dipyrromethene derivatives bearing N-alkyl phthalimide and amine substituents of potential application in the photoinactivation of bacteria},
journal = {Dyes and Pigments},
year = {2020},
volume = {178},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016%2Fj.dyepig.2020.108322},
pages = {108322},
doi = {10.1016/j.dyepig.2020.108322}
}