Nanomolar photodynamic activity of porphyrins bearing 1,4,7-trioxanonyl and 2-methyl-5-nitroimidazole moieties against cancer cells

Wierzchowski, Marcin; Łażewski, Dawid; Tardowski, Tadeusz; Grochocka, Małgorzata; Czajkowski, Rafał; Sobiak, Stanisław; Sobotta, Łukasz

doi:10.1016/j.jphotobiol.2019.111703

Cited by 7 publications

(4 citation statements)

References 54 publications

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“…Porphyrins play an important role in organisms such as hemoglobin, vitamin B12, cytochrome, and chlorophylls in humans, plants, and microorganisms. Moreover, porphyrins are important and well-studied photosensitizing agents for photodynamic therapy (PDT) due to their ability to be retained in tumors and to generate cytotoxic singlet oxygen under light irradiation. − In this work, (G/dG)-GNR hydrogels with encapsulation of 1 mM TPPS were prepared, and a certain amount of water was covered upon the hydrogel. This composite hydrogel was irradiated by CPL; then, the temperature was increased, and slow decomposition of the gel led to the TPPS molecules quickly diffusing from the hydrogel matrix into the water phase.…”

Section: Resultsmentioning

confidence: 99%

Guanosine Assembly Enabled Gold Nanorods with Dual Thermo- and Photoswitchable Plasmonic Chiroptical Activity

et al. 2020

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Noble metal nanostructures with plasmonic circular dichroism (PCD) have attracted interest, and a modulation of PCD is of great importance for their potential applications. Herein, we propose a supramolecular strategy for achieving dual thermal and photoswitchable PCD. When guanosine (G), deoxyguanosine (dG), and boric acid modified achiral gold nanorods (GNRs) were coassembled into a hydrogel, hybrid nanofibers with PCD were produced. When the hydrogel was heated, the nanofiber was disassembled and the PCD disappeared. As the hydrogel was thermally reversible, a thermo-controlled PCD could be realized. The hybrid hydrogel also showed photoswitchable PCD. When the gel was irradiated with an IR laser, the PCD disappeared. It can be restored by being placed at room temperature. Moreover, the hybrid gel was selectively responsive to the circularly polarized light (CPL). For (G/dG)-GNR hybrid assemblies, the R-CPL irradiation showed photothermal efficiency higher than that of L-CPL, which made it useful for an IR-irradiation-controlled release of drug molecules.

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Section: Resultsmentioning

confidence: 99%

Guanosine Assembly Enabled Gold Nanorods with Dual Thermo- and Photoswitchable Plasmonic Chiroptical Activity

et al. 2020

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“…The chain length also affects the circulation half-life, which prolongs with increases in molecular weight [ 34 ]. Conversely, short PEG chains can dramatically affect photosensitizer activity, as shown in our previous works [ 35 , 36 ]. As Hamblin and co-workers described it, PEGylation decreased the aggregation and reduced oxygen consumption during irradiation, which suggested a switch in photochemical mechanism from type II (singlet oxygen) to type I (radicals or electron transfer) [ 37 ].…”

Section: Introductionmentioning

confidence: 67%

“… Recently synthesized PEG-functionalized photosensitizers with long PEG chains: I—5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin (p-THPP) [ 39 ], II—3, 7-dibromo-2, 8-di (4-methoxyphenyl)-11-(phenyl-4-carbamoylo-PEG 2000 )-dithieno [2, 3-b]-[3, 2-g]-5, 5- difluoro-5-bora-3a, 4a-diaza-s-indacene) [ 40 ], and III—PEGylated Chlorin e6 polypeptide [ 41 ]; and short PEG chains: IV—Purpurin-PEG3-Amine Zinc Complex [ 38 ], V—2,7,12,18-tetramethyl-13,17-bis(1,4,7-trioxanonylcarbonylethyl)-3,8-divinylporphyrin [ 35 ], and VI—[1,4,8,11,15,18,22,25-octakis(1,4,7-trioxanonyl)phthalocyanine]zinc(II) [ 36 ]. …”

Section: Figurementioning

confidence: 99%

Novel Short PEG Chain-Substituted Porphyrins: Synthesis, Photochemistry, and In Vitro Photodynamic Activity against Cancer Cells

Łażewski

Kucińska

Potapskiy

et al. 2022

IJMS

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This work presents the synthesis and characterization of metal-free, zinc (II), and cobalt (II) porphyrins substituted with short PEG chains. The synthesized compounds were characterized by UV-Vis, 1H and 13C NMR spectroscopy, and MALDI-TOF mass spectrometry. The origin of the absorption bands for tested compounds in the UV-Vis range was determined using a computational model based on the electron density functional theory (DFT) and its time-dependent variant (TD-DFT). The photosensitizing activity was evaluated by measuring the ability to generate singlet oxygen (ΦΔ), which reached values up to 0.54. The photodynamic activity was tested using bladder (5637), prostate (LNCaP), and melanoma (A375) cancer cell lines. In vitro experiments clearly showed the structure–activity relationship regarding types of substituents, their positions in the phenyl ring, and the variety of central metal ions on the porphyrin core. Notably, the metal-free derivative 3 and its zinc derivative 6 exerted strong cytotoxic activity toward 5637 cells, with IC50 values of 8 and 15 nM, respectively. None of the tested compounds induced a cytotoxic effect without irradiation. In conclusion, these results highlight the potential value of the tested compounds for PDT application.

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“…The first, known as the Soret band, is located in the near-ultraviolet and the blue region of the visible spectrum. The second, called the Q band, appears in the low-energetic, red region of the visible spectrum [ 27 , 28 , 29 , 30 ]. The Soret band is a result of π-π* electron transitions upon light quant absorption and is related to movement of electrons from HOMO ( a 2 u ) orbital to the LUMO ( e g ) orbital [ 31 , 32 ].…”

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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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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Nanomolar photodynamic activity of porphyrins bearing 1,4,7-trioxanonyl and 2-methyl-5-nitroimidazole moieties against cancer cells

Cited by 7 publications

References 54 publications

Guanosine Assembly Enabled Gold Nanorods with Dual Thermo- and Photoswitchable Plasmonic Chiroptical Activity

Guanosine Assembly Enabled Gold Nanorods with Dual Thermo- and Photoswitchable Plasmonic Chiroptical Activity

Novel Short PEG Chain-Substituted Porphyrins: Synthesis, Photochemistry, and In Vitro Photodynamic Activity against Cancer Cells

Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

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