2020

Dyes and Pigments

Rocznik: 2020 | Tom: 178

artykuł naukowy

angielski

EN Novel boron-dipyrmmethene derivatives with N-alkyl phthalimide and amine substituents, including iodinated derivative, were synthesized and characterized using UV-Vis spectmphotometry, mass spectrometry (HRMS) and NMR spectroscopy. Non-iodinated analogs revealed high emission properties with fluorescence quantum yields (Phi(F)) between 0.48 and 0.58. But singlet oxygen generation quantum yields (Phi(Delta)) 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 Phi(F) values of about 0.02, but increased singlet oxygen generation abilities with excellent Phi(Delta) 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 mu M 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 mu M, 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.

108322

10.1016/j.dyepig.2020.108322

https://www.sciencedirect.com/science/article/pii/S0143720819323599?via%3Dihub

CC BY-NC-ND (uznanie autorstwa - użycie niekomercyjne - bez utworów zależnych)

ostateczna wersja opublikowana

03.2020

przed opublikowaniem

100

100