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Synthesis and In Vitro Photodynamic Activity of Cationic Boron Dipyrromethene-Based Photosensitizers Against Methicillin-Resistant Staphylococcus aureus

1
School of Biomedical Sciences, Faculty of Medicine, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong
2
Department of Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong
3
Department of Biomedical Sciences, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong
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Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong
5
State Key Laboratory of Research on Bioactivities and Clinical Applications of Medicinal Plants, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong
6
CUHK-Zhejiang University Joint Laboratory on Natural Products and Toxicology Research, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong
7
Department of Microbiology, Faculty of Medicine, The Chinese University of Hong Kong, Prince of Wales Hospital, Shatin, N.T., Hong Kong
8
Shenzhen Research Institute, The Chinese University of Hong Kong, Shenzhen 518057, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Biomedicines 2020, 8(6), 140; https://doi.org/10.3390/biomedicines8060140
Received: 18 May 2020 / Revised: 25 May 2020 / Accepted: 26 May 2020 / Published: 29 May 2020
(This article belongs to the Section Therapeutic Strategies in Different Diseases)
A series of cationic boron dipyrromethene (BODIPY) derivatives were synthesized and characterized with various spectroscopic methods. Having the ability to generate singlet oxygen upon irradiation, these compounds could potentially serve as photosensitizers for antimicrobial photodynamic therapy. Of the five BODIPYs being examined, the dicationic aza-BODIPY analogue (compound 5) demonstrated the highest potency against a broad spectrum of clinically relevant methicillin-resistant Staphylococcus aureus (MRSA), including four ATCC-type strains (ATCC 43300, ATCC BAA-42, ATCC BAA-43, and ATCC BAA-44), two strains carrying specific antibiotic resistance mechanisms [-AAC(6’)-APH(2”) and RN4220/pUL5054], and ten non-duplicate clinical strains from hospital- and community-associated MRSAs of the important clonal types ST239, ST30, and ST59, which have previously been documented to be prevalent in Hong Kong and its neighboring countries. The in vitro anti-MRSA activity of compound 5 was achieved upon irradiation with near-infrared light (>610 nm) with minimal bactericidal concentrations (MBCs) ranging from 12.5 to 25 µM against the whole panel of MRSAs, except the hospital-associated MRSAs for which the MBCs were in the range of 50–100 µM. Compound 5 was significantly (p < 0.05) more potent than methylene blue, which is a clinically approved photosensitizer, indicating that it is a promising antimicrobial agent that is worthy of further investigation. View Full-Text
Keywords: antimicrobials; boron dipyrromethenes; methicillin-resistant Staphylococcus aureus; photodynamic therapy; photosensitizers antimicrobials; boron dipyrromethenes; methicillin-resistant Staphylococcus aureus; photodynamic therapy; photosensitizers
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Dharmaratne, P.; Wong, R.C.H.; Wang, J.; Lo, P.-C.; Wang, B.; Chan, B.C.L.; Lau, K.-M.; Lau, C.B.S.; Fung, K.-P.; Ip, M.; Ng, D.K.P. Synthesis and In Vitro Photodynamic Activity of Cationic Boron Dipyrromethene-Based Photosensitizers Against Methicillin-Resistant Staphylococcus aureus. Biomedicines 2020, 8, 140.

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