Tribenzoporphyrazines with dendrimeric peripheral substituents and their promising photocytotoxic activity against Staphylococcus aureus

Mlynarczyk, Dariusz T.; Długaszewska, Jolanta; Falkowski, Michał; Popenda, Łukasz; Kryjewski, Michał; Szczołko, Wojciech; Jurga, Stefan; Mielcarek, Jadwiga; Gośliński, Tomasz

doi:10.1016/j.jphotobiol.2020.111803

Cited by 12 publications

(13 citation statements)

References 27 publications

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“…Among the studied macrocycles, tribenzoporphyrazine 1 presented the highest S. aureus killing rate of over 5.9 log at the concentration of 10 −5 M, and under irradiation with a relatively low light dose of 30 J/cm 2 . Similar results of S. aureus photodynamic inactivation was reported before [ 56 ]. Interestingly, at higher concentrations, studied compounds revealed lower photodynamic bacterial growth reduction potential.…”

Section: Resultssupporting

confidence: 91%

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Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

Stolarska

Glowacka-Sobotta

Mlynarczyk

et al. 2020

IJMS

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Magnesium(II) tribenzoporphyrazines with phenoxybutylsulfanyl substituents were evaluated as photosensitizers in terms of their optical properties against wound bacteria. In the UV-vis spectra of analyzed tribenzoporphyrazines, typical absorption ranges were found. However, the emission properties were very weak, with fluorescence quantum yields in the range of only 0.002–0.051. What is important, they revealed moderate abilities to form singlet oxygen with the quantum yields up to 0.27. Under irradiation, the macrocycles decomposed via photobleaching mechanism with the quantum yields up to 8.64 × 10−5. The photokilling potential of tribenzoporphyrazines was assessed against Streptococcus pyogenes, Staphylococcus epidermidis, as well as various strains of Staphylococcus aureus, including methicillin-sensitive and-resistant bacteria. Both evaluated photosensitizers revealed high photodynamic potential against studied bacteria (>3 logs). S.aureus growth was reduced by over 5.9 log, methicillin-resistant S. aureus by 5.1 log, S.epidermidis by over 5.7 log, and S. pyogenes by over 4.7 log.

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Section: Resultssupporting

confidence: 91%

“…The average diameter of the obtained liposomes was measured at 301 nm, 188 nm, and 119 nm for 1, 2, and MgPc, respectively ( Table 2 ). Liposome vehicles were used for solubilization of lipophilic photosensitizers enabling to keep them in the monomeric, non-aggregated forms, which is necessary for high photodynamic activity [ 56 ].…”

Section: Resultsmentioning

confidence: 99%

Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

Stolarska

Glowacka-Sobotta

Mlynarczyk

et al. 2020

IJMS

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“…The experiments were performed according to previously elaborated procedures. [33,69,70] The bacteria were cultured aerobically in BHI broth at 36 � 1°C for 18-20 h, and subsequently harvested by centrifugation (3000 rpm for 15 min). The obtained pellet was resuspended in phosphate buffered saline (PBS, pH = 7.0, Sigma-Aldrich) and diluted with PBS to a final concentration of ca.…”

Section: In Vitro Photodynamic Inactivation Of Planktonic Bacteriamentioning

confidence: 99%

“…[8,22] Noteworthy BODIPY 5 also showed better efficiency against E. coli, than phthalocyanines, chlorins, and porphyrazines, previously tested in our team. [66,69,70,73,74] Not many reports concerning cationic BODIPY derivatives with photodynamic antimicrobial activity have been published so far. Two cationic derivatives with 4-(trimethylammonium) phenyl and 4-(3-(trimethylammonium)propoxy)phenyl groups have been applied as photosensitizing agents against S. aureus and E. coli.…”

Section: In Vitro Photodynamic Inactivation Of Planktonic Bacteriamentioning

confidence: 99%

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

et al. 2020

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Boron‐dipyrromethene derivatives, including cationic and iodinated analogs, were obtained and subjected to physicochemical and in vitro photodynamic activity studies. Iodinated derivatives revealed a substantial heavy atom effect manifested by a bathochromic shift of the absorption band by about 30 nm and fluorescence intensity reduced by about 30–35 times, compared to that obtained for non‐iodinated ones. In consequence, singlet oxygen generation significantly increased with ΦΔ values in the range 0.69–0.97. The in vitro photodynamic activity was evaluated on Gram‐positive Staphylococcus aureus, Gram‐negative Escherichia coli, and on human androgen‐sensitive prostate adenocarcinoma cells (LNCaP). The novel cationic, iodinated BODIPY, demonstrated the highest activity toward all studied cells. An excellent cytotoxic effect was found against LNCaP cells with an IC50 value of 19.3 nM, whereas the viability of S. aureus was reduced by >5.6 log10 at 0.25 μM concentration and by >5.3 log10 in the case of E. coli at 5 μM. Thus, this analog seems to be a very promising candidate for the application in both anticancer and antimicrobial photodynamic therapy.

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“…Despite the increased number of available antiseptics and disinfectants, bacterial infection remains a major health problem, including dental plaque, dermal and oral infections, urinary tract infections, and implant- or catheter-associated infections [ 23 , 24 , 25 , 26 , 27 , 28 ]. The presence of antibiotic-resistant bacteria still requires research on other strategies to eradicate bacteria resistant to many drugs [ 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Photodynamic Inactivation of Bacteria with Porphyrin Derivatives: Effect of Charge, Lipophilicity, ROS Generation, and Cellular Uptake on Their Biological Activity In Vitro

Sułek

Pucelik

Kobielusz

et al. 2020

IJMS

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Resistance of microorganisms to antibiotics has led to research on various therapeutic strategies with different mechanisms of action, including photodynamic inactivation (PDI). In this work, we evaluated a cationic, neutral, and anionic meso-tetraphenylporphyrin derivative’s ability to inactivate the Gram-negative and Gram-positive bacteria in a planktonic suspension under blue light irradiation. The spectroscopic, physicochemical, redox properties, as well as reactive oxygen species (ROS) generation capacity by a set of photosensitizers varying in lipophilicity were investigated. The theoretical calculations were performed to explain the distribution of the molecular charges in the evaluated compounds. Moreover, logP partition coefficients, cellular uptake, and phototoxicity of the photosensitizers towards bacteria were determined. The role of a specific microbial efflux pump inhibitor, verapamil hydrochloride, in PDI was also studied. The results showed that E. coli exhibited higher resistance to PDI than S. aureus (3–5 logs) with low light doses (1–10 J/cm2). In turn, the prolongation of irradiation (up to 100 J/cm2) remarkably improved the inactivation of pathogens (up to 7 logs) and revealed the importance of photosensitizer photostability. The PDI potentiation occurs after the addition of KI (more than 3 logs extra killing). Verapamil increased the uptake of photosensitizers (especially in E. coli) due to efflux pump inhibition. This effect suggests that PDI is mediated by ROS, the electrostatic charge interaction, and the efflux of photosensitizers (PSs) regulated by multidrug-resistance (MDR) systems. Thus, MDR inhibition combined with PDI gives opportunities to treat more resistant bacteria.

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Tribenzoporphyrazines with dendrimeric peripheral substituents and their promising photocytotoxic activity against Staphylococcus aureus

Cited by 12 publications

References 27 publications

Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

Photodynamic Inactivation of Bacteria with Porphyrin Derivatives: Effect of Charge, Lipophilicity, ROS Generation, and Cellular Uptake on Their Biological Activity In Vitro

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