Synthesis and photodynamic efficacy of water-soluble protoporphyrin IX homologue with mPEG550

Başoğlu, Harun; Değirmencioğlu, İsmail; Eyüpoğlu, Figen Celep

doi:10.1016/j.pdpdt.2021.102615

Cited by 5 publications

(3 citation statements)

References 29 publications

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“…Regrettably, ZnPP is prone to aggregation in aqueous solutions like other metalloporphyrins, which causes not only self-quenching, but also shorter blood circulation times and lower enrichment efficiency and is limited in practical application. In recent years, people have developed many methods of water-soluble modification, such as polyethylene glycol (PEG) [ 38 ], PLGA [ 39 ], albumin [ 40 ], of which the United States Food and Drug Administration (FDA) prefers PEG due to its higher biocompatibility and water solubility, lower immunogenicity, and lower toxicity [ 41 ]. In this study, we developed an improved water-soluble method to solve the low efficiency of polyethylene glycol (PEG)-conjugated metalloporphyrin and found that its high concentration (1 mM) maintained better water solubility (for a period of 30 days).…”

Section: Discussionmentioning

confidence: 99%

Antitumor Effects of Pegylated Zinc Protoporphyrin-Mediated Sonodynamic Therapy in Ovarian Cancer

Li,

Hu,

Zhu

et al. 2023

Pharmaceutics

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Sonodynamic therapy (SDT) induces reactive oxygen species (ROS) to kill tumor cells. Heme oxygenase-1 (HO-1), as an important antioxidant enzyme, resists killing by scavenging ROS. Zinc protoporphyrin (ZnPP) not only effectively inhibits HO-1 activity, but also becomes a potential sonosensitizer. However, its poor water solubility limits its applications. Herein, we developed an improved water-soluble method. It was proved that pegylated zinc protoporphyrin-mediated SDT (PEG-ZnPP-SDT) could significantly enhance ROS production by destroying the HO-1 antioxidant system in ovarian cancer. Increased ROS could cause mitochondrial membrane potential collapse, release cytochrome c from mitochondria to the cytoplasm, and trigger the mitochondrial–caspase apoptotic pathway. In conclusion, our results demonstrated that PEG-ZnPP-SDT, as a novel sonosensitizer, could improve the antitumor effects by destroying the HO-1 antioxidant system. It provided a new therapeutic strategy for SDT to treat cancers, especially those with higher HO-1 expression.

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Section: Discussionmentioning

confidence: 99%

Antitumor Effects of Pegylated Zinc Protoporphyrin-Mediated Sonodynamic Therapy in Ovarian Cancer

Li,

Hu,

Zhu

et al. 2023

Pharmaceutics

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“…Therefore, it forms aggregates in aqueous solutions due to its amphiphilic properties . Therefore, the structure of PPIX was modified to increase the solubility of this PS in biological media. ,− On the other hand, CS is a linear polycationic polymer produced in nature that has numerous applications in biomedicine, environmental sciences, food production, and agricultural industries. , This biocompatible and biodegradable polysaccharide exhibits a wide range of antibacterial and antifungal activity . Furthermore, CS derivatives showed promising applications in food processing, packaging, and ingredients .…”

Section: Introductionmentioning

confidence: 99%

Development of New Photoinactivation Strategies for Microbial Decontamination in Fruits and Packaging

Larrea,

Gsponer,

Durantini

et al. 2023

ACS Food Sci. Technol.

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The consumption of fruits and vegetables in the daily diet is an adequate condition for obtaining a healthy life. Therefore, decontamination is crucial to reducing the appearance of potentially dangerous microorganisms in these foods. In this work, a conjugate (CS−PPIX) of natural origin was synthesized from the covalent union of protoporphyrin IX (PPIX) and chitosan (CS) by amide bonds. This photosensitizer was developed to reduce the microbial load in fruits and food packaging through the photodynamic inactivation of microorganisms (PDI). A film of CS−PPIX showed an appreciable contact surface. The conjugation of PPIX to CS was confirmed by IR spectra. The absorption and emission spectra of the conjugate exhibited the characteristic PPIX bands, accompanied by a fluorescence quantum yield of 0.10. Photodynamic investigation indicated that CS−PPIX produced singlet molecular oxygen (Φ Δ = 0.40) in solution. Also, this compound was able to generate superoxide anion radicals with the assistance of the reductant nicotinamide adenine dinucleotide and efficiently photo-oxidize the amino acid L-tryptophan. PDI in vitro experiments were performed with the Gram-positive bacterium Staphylococcus aureus. Bacteria were eliminated (>99.9999% reduction in survival) when cell suspensions were treated with 1 μM CS−PPIX upon 30 min of irradiation with white light. Furthermore, no microbial growth was detected in cells immobilized on agar surfaces in the CS−PPIX-treated areas. Therefore, the PDI approach was evaluated to reduce the contamination of S. aureus on fruit surfaces and food containers. After treating the surfaces of apple and pear pieces with 10 nmol of CS−PPIX, a greater than 99.9% reduction in bacterial survival was observed upon an irradiation of 30 min. This conjugate was also effective in the photodynamic decontamination of polyethylene bags and polyethylene terephthalate packaging materials. Therefore, the CS−PPIX conjugate presents adequate properties to reduce the microbial load and preserve fresh foods.

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“…The use of water‐soluble groups to improve the aqueous solubility of PpIX is an efficient approach and includes the esterification of the carboxylic acid groups of PpIX with methoxy‐PEG groups. The water‐soluble PpIX compounds generated 22,23 maintain their excellent fluorescence properties and have been applied in PDT and fluorescent imaging in vivo. Therefore, the synthesis of water‐soluble PpIX derivatives will be of great significance to the further clinical application of PpIX based materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water‐soluble protoporphyrin IX polymers and their photodynamic application

Shi

Pan

et al. 2022

J of Applied Polymer Sci

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Protoporphyrin IX (PpIX) is a photosensitizer used in photodynamic therapy, however, its poor aqueous solubility always presents challenges and limits its application. To solve these problems water‐soluble derivatives of PpIX were synthesized by esterification with polyethylene glycol, and polymerization of the PpIX diol with hexamethylene diisocyanate to form a water‐soluble polyurethane. The polyurethane PpIX derivatives were characterized and showed high levels of singlet oxygen generation. The photodynamic antibacterial activity of the PpIX derivatives were explored on Escherichia coli, Staphylococcus aureus and methicillin‐resistant Staphylococcus aureus indicated that 100% antibacterial killing was achieved with a concentration of 40 μM upon 405 nm irradiation for 5 min. The polyurethane showed high biocompatibility in the dark with a variety of cell lines, but when exposed to 405 nm light (for 5 min) cytotoxic singlet oxygen was generated, resulting in cell death. Importantly, this was also possible with 635 nm illumination. In summary this novel protoporphyrin polyurethane overcomes the issues of solubility, and offers enhanced killing (singlet oxygen) generation with the potential to be used in photodynamic therapy for both antibacterial and anticancer treatment.

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Synthesis and photodynamic efficacy of water-soluble protoporphyrin IX homologue with mPEG550

Cited by 5 publications

References 29 publications

Antitumor Effects of Pegylated Zinc Protoporphyrin-Mediated Sonodynamic Therapy in Ovarian Cancer

Antitumor Effects of Pegylated Zinc Protoporphyrin-Mediated Sonodynamic Therapy in Ovarian Cancer

Development of New Photoinactivation Strategies for Microbial Decontamination in Fruits and Packaging

Synthesis of water‐soluble protoporphyrin IX polymers and their photodynamic application

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