Non-porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria

Sobotta, Łukasz; Skupin-Mrugalska, Paulina; Piskorz, Jaroslaw; Mielcarek, Jadwiga

doi:10.1016/j.dyepig.2018.12.014

Cited by 62 publications

(48 citation statements)

References 174 publications

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“…The selection of RB in that previous study was not only due to its commercial accessibility, but also owing to its high 1 O 2 quantum yield [44] as well as its known ability to inactivate microorganisms [45]. In addition, RB has also been widely used as a dye in the diagnosis of eye diseases [46] and as a food colorant [47]; as such, its safety profile has been established, an advantage over custom-made photosensitizers. The immobilization of RB and cationic dyes on wool/acrylic (W/A) fabrics is based on the ionic affinity and van der Waals attractions between the dyes and fibers.…”

Section: Introductionmentioning

confidence: 99%

Color-Variable Photodynamic Antimicrobial Wool/Acrylic Blended Fabrics

et al. 2020

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Towards the goal of developing scalable, economical and effective antimicrobial textiles to reduce infection transmission, here we prepared color-variable photodynamic materials comprised of photosensitizer (PS)-loaded wool/acrylic (W/A) blends. Wool fibers in the W/A blended fabrics were loaded with the photosensitizer rose bengal (RB), and the acrylic fibers were dyed with a variety of traditional cationic dyes (cationic yellow, cationic blue and cationic red) to broaden their color range. Investigations on the colorimetric and photodynamic properties of a series of these materials were implemented through CIELab evaluation, as well as photooxidation and antibacterial studies. Generally, the photodynamic efficacy of these dual-dyed fabrics was impacted by both the choice, and how much of the traditional cationic dye was employed in the dyeing of the W/A fabrics. When compared with the PS-only singly-dyed material, RB-W/A, that showed a 99.97% (3.5 log units; p = 0.02) reduction of Staphylococcus aureus under visible light illumination (λ ≥ 420 nm, 60 min), the addition of cationic dyes led to a slight decrease in the photoinactivation ability of the dual-dyed fabrics, but was still able to achieve a 99.3% inactivation of S. aureus. Overall, our findings demonstrate the feasibility and potential applications of low cost and color variable RB-loaded W/A blended fabrics as effective self-disinfecting textiles against pathogen transmission.

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Section: Introductionmentioning

confidence: 99%

Color-Variable Photodynamic Antimicrobial Wool/Acrylic Blended Fabrics

et al. 2020

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“…It is worth mentioning that, mainly in dermatology, even UVB irradiation is considered of therapeutic use [16][17][18]. Besides the anticancer activities of photosensitizers [19][20][21], "post-antibiotic era" is experimenting with photosensitizers as alternative therapeutics for the fight against multiresistant bacteria both for medicinal [22][23][24][25] and environmental purposes [26,27].…”

Section: Introductionmentioning

confidence: 99%

“…Based on our interest in the chemistry and biology of the oxime functionality [54][55][56][57], as well as in their DNA photolytic interaction upon UV irradiation [9][10][11]43] we have decided to investigate the behaviour of carefully designed O-carbamoyl derivatives of p-pyridine amidoxime, ethanone oxime and aldoxime (VI, VII, VIII, R 1 = p-pyridyl, Figure 1) as DNA photosensitizers. Based on our previous ex-Scheme 1: Synthesis of O-carbamoyl amidoximes (8)(9)(10)(11)(12)(13), ethanone oximes (15)(16)(17)(18)(19)(20) and aldoximes (22)(23)(24)(25)(26)(27). Oxime 1 or 14 or 21, Et 3 N (1.1 equiv), R-NCO (1.1-1.8 equiv), dry chloroform or tetrahydrofuran, Ar, 0 °C → rt or reflux, 19-97%.…”

Section: Introductionmentioning

confidence: 99%

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

Gritzapis

Varras

Andreou

et al. 2020

Beilstein J. Org. Chem.

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A number of p-pyridinyl oxime carbamate derivatives were prepared upon the reaction of the corresponding oximes with isocyanates. These novel compounds reacted photochemically in the presence of supercoiled plasmid DNA. Structure–activity relationship (SAR) studies revealed that the substituent on the imine group was not affecting the extend of the DNA damage, whereas the substituent of the carbamate group was critical, with the halogenated derivatives to be able to cause extensive single and double stranded DNA cleavages, acting as “synthetic nucleases”, independently of oxygen and pH. Calf thymus–DNA affinity studies showed a good-to-excellent affinity of selected both active and non-active derivatives. Preliminary theoretical studies were performed, in an effort to explain the reasons why some derivatives cause photocleavage and some others not, which were experimentally verified using triplet state activators and quenchers. These theoretical studies seem to allow the prediction of the activity of derivatives able to pass intersystem crossing to their triplet energy state and thus create radicals able to damage DNA. With this study, it is shown that oxime carbamate derivatives have the potential to act as novel effective photobase generating DNA-photocleavers, and are proposed as new leads for “on demand” biotechnological applications in drug discovery and medicine.

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“…An increasing number of recent publications have demonstrated the potential of PDT for the inactivation of microorganisms. For example, non-porphyrinoid photosensitizer-mediated photodynamic can inactivate bacteria (Sobotta et al, 2019), curcumin-mediated photodynamic action could inactivate Vibrio parahaemolyticus cells to undetectable level (Wu et al, 2016), blue light with curcumin can inhibit Propionibacterium acnes (Yang et al, 2018), bacterial viability reduces after exposure to curcumin at 75 mM and LED light doses of 139, 278, and 417 J/cm 2 (Penha et al, 2017), curcumin-mediated PDT can kill Burkholderia cepacia (Hu et al, 2018), and curcumin has been used as a photosensitizer to reduce microbial populations and prolong the shelf-life of oysters (Liu et al, 2016). These data have drawn our attention to the potential of PDT technology in the food industry; however, the application of photodynamic LEDactivated curcumin for use in the disinfection of fresh fruits has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Inactivation of microbes on fruit surfaces using photodynamic therapy and its influence on the postharvest shelf-life of fruits

Zhang

et al. 2020

Food sci. technol. int.

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In this study, the disinfection effect of curcumin-mediated photodynamic therapy on the contact surfaces of fresh fruit was investigated. Our results showed that the optimum concentration of curcumin and the energy density required were 0.5 μM and 7.2 J/cm2, respectively. Photodynamic therapy showed an excellent disinfection rate for the fresh fruits with a reduction of more than 80% in the total bacteria and coliform counts. The photodynamic therapy inhibited species that belonged to the categories of gram-negative and facultative anaerobic bacteria, except for two species of the Trichoderma fungus. Importantly, photodynamic therapy prolonged the shelf-life of grapes for two days at room temperature. Therefore, photodynamic therapy should be commercialized as a high efficiency and non-thermal sterilization technology for use in the food industry.

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Non-porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria

Cited by 62 publications

References 174 publications

Color-Variable Photodynamic Antimicrobial Wool/Acrylic Blended Fabrics

Color-Variable Photodynamic Antimicrobial Wool/Acrylic Blended Fabrics

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

Inactivation of microbes on fruit surfaces using photodynamic therapy and its influence on the postharvest shelf-life of fruits

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