Photoactivities of Vitamin K Derivatives and Potential Applications as Daylight-Activated Antimicrobial Agents

Abstract

Photoactivities of four natural or naturalderivatized vitamin K (VK) species were investigated by using a combination of theoretical computational modeling, prediction, and specially designed experimental tests. The results revealed that these VK compounds are photoactive in the generation of reactive oxygen species of hydroxyl radicals and singlet oxygen under daylight, UVA, and UVB irradiations. Two possible photoreaction paths exist in an environment of good or poor hydrogen donors. Vitamin K 3 (VK 3 ), as an aromatic naphthoquinone compound, was predicted and demonstrated as the most effective photoactive agent under a broad range of UV−vis wavelengths and in production of both hydroxyl radicals and singlet oxygen. VK 1 and VK 2 are less active than VK 3 due to the existence of double bonds in their side chains of naphthoquinone. VK 4 is different in photoactivity due to the loss of an aromatic ketone structure. As an example, VK 3 was tested against Gram-negative Escherichia coli and Gram-positive Listeria innocua under daylight irradiation and exhibited complete kill of Escherichia coli (six log reduction in 60 min of daylight exposure) and Listeria innocua (five log reduction in 90 min of daylight exposure). In addition, VK 3 retained its high bactericidal efficacy toward both Escherichia coli and Listeria innocua after seven times of repeated daylight exposures, indicating excellent reusability as a green biocide. This work provides insight into the development of green and sustainable photoinduced antimicrobial materials for biomedical and food safety applications.

Unique “posture” of rose Bengal for fabricating personal protective equipment with enhanced daylight-induced biocidal efficiency

“…Reactive oxygen species, including hydroxyl radical (HO•) and singlet oxygen ( 1 O 2 ), were measured by p-NDA and p-NDA/L-histidine in phosphate-buffered saline (PBS, pH = 7.4), respectively. 12,28 To avoid the physical adsorption of p-NDA by the fabrics, the fibrous samples were immersed in 50 mL 40 μM of p-NDA solution for 24 hours under dark. Then, the fabric (2×2 cm 2 , ~50 mg) was immersed in 10 mL 40 μM p-NDA solution in a glass petri dish and exposed to daylight in an XL-1500 crosslinker for different durations for examining ROS production.…”

“…Thus, the development of innovative materials that can aggressively attack the pathogens has attracted much attention. For instance, antibacterial agents including silver nanoparticles, 5,6 TiO 2 , 7 N-halamines, [8][9][10] and organic photosensitizers [11][12][13][14] were incorporated onto PPE for providing enhanced protection by disinfecting and deactivating pathogens. Among them, organic photosensitizers (PS) (i.e., mostly are dyes) can generate reactive oxygen species (ROS), including hydroxyl radicals (HO•), hydroperoxide radical (HOO•), hydrogen peroxides (H 2 O 2 ), and singlet oxygen ( 1 O 2 ), under light irradiation.…”

“…The resultant materials performed outstanding biocidal functions against bacteria (E. coli and S. innocua) and viruses (T7 bacteriophage and coronavirus). 12,17 Xanthene dyes, such as rose Bengal (RB), have been applied as antibacterial agents to functionalize textiles through the conventional dyeing process. Natural or synthetic polyamides were dyed with RB based on the electrostatic interaction at an acidic condition.…”

Natural bioactive substances for the control of food-borne viruses and contaminants in food

“…Antimicrobial activities were also found in other Saponin-rich extracts from plants, such as guar, quillaja, yucca, and soybean (Hassan et al 2010 ). Moreover, vitamin K could be used as a green biocide with high bactericidal efficacy toward both Escherichia coli and Listeria innocua after seven times repeated daylight exposure (Zhang et al 2019 ). Vitamin D was also proven to innate immunity by regulating the production of antimicrobial peptides and cytokine response, which show its potential for use as antimicrobial drugs (Youssef et al 2011 ).…”

Daylight-Active Cellulose Nanocrystals Containing Anthraquinone Structures

“…Species that can absorb long-wavelength ultraviolet light (UVA) or daylight and become excited to produce reactive oxygen species (ROS), including hydrogen peroxide, hydroxyl radicals, and even singlet oxygen [5,6], are ideal candidates as functional groups. The ROS would provide antibacterial and self-disinfecting properties for the modified materials, as well as being environmentally friendly since they only require light exposure and oxygen to function [7][8][9][10].…”