A quaternary ammonium modified coumarin derivative for antimicrobial photodynamic therapy

Zhiyuan Sun; Shaona Zhou; Ying Gu; Yuxia Zhao

doi:10.1117/12.2287086

8 February 2018 A quaternary ammonium modified coumarin derivative for antimicrobial photodynamic therapy

Zhiyuan Sun, Shaona Zhou, Ying Gu, Yuxia Zhao

Proceedings Volume 10479, Light-Based Diagnosis and Treatment of Infectious Diseases; 104790Z (2018) https://doi.org/10.1117/12.2287086
Event: SPIE BiOS, 2018, San Francisco, California, United States

Abstract

A new cationic modified coumarin derivative, 7-diethylamino-3-(3-(4-(trimethylbenzenaminium iodide) phenyl) acryloyl)-2H-chromen-2-one (1), was synthesized and characterized by ¹H NMR and mass spectra. It had a strong intramolecular charge transfer absorption band around 460 nm with large molar extinction coefficients of 3.94 × 10⁴ M^-1 cm^-1 in DMF and 3.86 × 10⁴ M^-1 cm^-1 in PBS, respectively. Moreover, a moderate singlet oxygen quantum yield of 0.16 was obtained for 1 in DMF. Using methylene blue (MB) under a 630 nm laser as reference, the in vitro antimicrobial photodynamic therapy (aPDT) activity of 1 against three strains, gram positive bacteria methicillin-resistant staphylococcus aureus (MRSA), negative bacteria acinetobacter baumannii (A. baumannii) and fungus Candida albicans (C. albicans), was carried out by irradiation with a 457 nm laser. It was shown that 1 had no dark toxicity to these bacteria when its concentration was up to 100 μM, while under the 457 nm laser it could kill them effectively with an over 3 log CFU/ml decrease of the bacterial viability with its concentration up to 5 μM. The aPDT capability of 1 against MRSA and A. baumannii was equivalent to that of MB. For C. albicans, 1 exhibited much better aPDT effect than MB.

Citation Download Citation

Zhiyuan Sun, Shaona Zhou, Ying Gu, and Yuxia Zhao "A quaternary ammonium modified coumarin derivative for antimicrobial photodynamic therapy", Proc. SPIE 10479, Light-Based Diagnosis and Treatment of Infectious Diseases, 104790Z (8 February 2018); https://doi.org/10.1117/12.2287086

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