Quaternized Curcumin Derivative—Synthesis, Physicochemical Characteristics, and Photocytotoxicity, Including Antibacterial Activity after Irradiation with Blue Light

Bakun, P ORCID: 0000-0002-0831-2856, Wysocki, M ORCID: 0000-0003-3585-2716, Stachowiak, M, Musielak, M ORCID: 0000-0002-8187-2446, Dlugaszewska, J ORCID: 0000-0002-2192-3715, Mlynarczyk, DT ORCID: 0000-0003-3583-0752, Sobotta, L ORCID: 0000-0002-5062-4503, Suchorska, WM and Goslinski, T ORCID: 0000-0001-5705-5414 (2024) Quaternized Curcumin Derivative—Synthesis, Physicochemical Characteristics, and Photocytotoxicity, Including Antibacterial Activity after Irradiation with Blue Light. Molecules, 29 (19). ISSN 1420-3049

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Abstract

Over the past few years, numerous bacterial strains have become resistant to selected drugs from various therapeutic groups. A potential tool in the fight against these strains is antimicrobial photodynamic therapy (APDT). APDT acts in a non-specific manner by generating reactive oxygen species and radicals, thereby inducing multidimensional intracellular effects. Importantly, the chance that bacteria will develop defense mechanisms against APDT is considered to be low. In our research, we performed the synthesis and physicochemical characterization of curcumin derivatives enriched with morpholine motifs. The obtained compounds were assessed regarding photostability, singlet oxygen generation, aggregation, and acute toxicity toward prokaryotic Aliivibrio fischeri cells in the Microtox^® test. The impact of the compounds on the survival of eukaryotic cells in the MTT assay was also tested (WM266-4, WM115—melanoma, MRC-5—lung fibroblasts, and PHDF—primary human dermal fibroblasts). Initial studies determining the photocytotoxicity, and thus the potential APDT usability, were conducted with the following microbial strains: Candida albicans, Escherichia coli, Staphylococcus aureus, Streptococcus pneumoniae, and Pseudomonas aeruginosa. It was noted that the exposure of bacteria to LED light at 470 nm (fluence: 30 J/cm²) in the presence of quaternized curcumin derivatives at the conc. of 10 µM led to a reduction in Staphylococcus aureus survival of over 5.4 log.

Item Type:	Article
Uncontrolled Keywords:	curcumin derivatives; PACT; Microtox; morpholine; MTT; toxicity; Humans; Bacteria; Pseudomonas aeruginosa; Singlet Oxygen; Curcumin; Photosensitizing Agents; Anti-Bacterial Agents; Photochemotherapy; Microbial Sensitivity Tests; Cell Survival; Light; Aliivibrio fischeri; Blue Light; MTT; Microtox; PACT; curcumin derivatives; morpholine; toxicity; Curcumin; Humans; Anti-Bacterial Agents; Light; Microbial Sensitivity Tests; Aliivibrio fischeri; Photosensitizing Agents; Cell Survival; Singlet Oxygen; Pseudomonas aeruginosa; Photochemotherapy; Bacteria; Blue Light; 3404 Medicinal and Biomolecular Chemistry; 3405 Organic Chemistry; 34 Chemical Sciences; Antimicrobial Resistance; Emerging Infectious Diseases; Lung; Complementary and Integrative Health; Infectious Diseases; 2.2 Factors relating to the physical environment; 5.1 Pharmaceuticals; Infection; Curcumin; Humans; Anti-Bacterial Agents; Light; Microbial Sensitivity Tests; Aliivibrio fischeri; Photosensitizing Agents; Cell Survival; Singlet Oxygen; Pseudomonas aeruginosa; Photochemotherapy; Bacteria; Blue Light; 0304 Medicinal and Biomolecular Chemistry; 0305 Organic Chemistry; 0307 Theoretical and Computational Chemistry; Organic Chemistry; 3404 Medicinal and biomolecular chemistry; 3405 Organic chemistry
Subjects:	R Medicine > RS Pharmacy and materia medica
Divisions:	Pharmacy and Biomolecular Sciences
Publisher:	MDPI
Date of acceptance:	20 September 2024
Date of first compliant Open Access:	15 October 2026
Date Deposited:	15 Oct 2026 12:31
Last Modified:	15 Oct 2026 12:31
DOI or ID number:	10.3390/molecules29194536
URI:	https://researchonline.ljmu.ac.uk/id/eprint/29688

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