Development of novel formulations for photodynamic therapy on the basis of amphiphilic polymers and porphyrin photosensitizers. Porphyrin-polymer complexes in model photosensitized processes

Aksenova, N. P.; Oleś, T.; Sarna, Tadeusz; Глаголев, Н. Н.; Chernjak, A. V.; Volkov, V. I.; Kotova, Svetlana; Melik‐Nubarov, N. S.; Solovieva, Anna B.

doi:10.1134/s1054660x12100015

Cited by 21 publications

(13 citation statements)

References 38 publications

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“…This observation strongly indicates that Ce6 localizes in the interface region between PPO and PEO block, interacting with both hydrophobic and hydrophilic parts of Pluronic micelle. These observations clearly agree with our previously published results concerning Pluronic and PVP interactions with another amphiphilic porphyrindimegin (48). Similarly, interaction of Ce6 with PVP molecule occurs via Van-der-Waals interactions of the porphyrin ring and hydrophobic substituents with the polymer backbone and dipolar and hydrogen bonding interactions of carboxylic groups with pyrrolidone rings.…”

Section: Uv/vis Spectroscopic Studies Of Chlorin E6 Interaction Withsupporting

confidence: 93%

Complexes of Chlorin e6 with Pluronics and Polyvinylpyrrolidone: Structure and Photodynamic Activity in Cell Culture

Zhiyentayev

Boltaev

Соловьева

et al. 2013

Photochem & Photobiology

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Polymeric carriers are extensively used in photodynamic therapy (PDT) for increase of efficacy of photosensitizers. Here, we report the influence of nine Pluronic copolymers on phototoxicity of chlorin e6 (Ce6), in particular 5- to 7-fold rise in the phototoxicity caused by hydrophilic Pluronics F127, F108, F68 and F87 and practically no influence on Ce6 of more hydrophobic polymers. The revealed value of 0.2 mg mL(-1) of Pluronic F127 concentration sufficient for half-of-maximal increase of Ce6 photodynamic activity proved to be close to 0.16 mg mL(-1) inherent in well-documented carrier poly(N-vinylpyrrolidone) (PVP). The dissociation constants of Ce6 complexes with Pluronic F127 and PVP that were estimated from UV spectra were 0.252 and 0.036 mg mL(-1) , respectively, indicating higher stability of Ce6 complex with PVP. According to the results of (1) H-NMR studies of Ce6 complexes, the porphyrin interacts not only with hydrophobic regions but also with hydrophilic sides of both polymers.

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Section: Uv/vis Spectroscopic Studies Of Chlorin E6 Interaction Withsupporting

confidence: 93%

Complexes of Chlorin e6 with Pluronics and Polyvinylpyrrolidone: Structure and Photodynamic Activity in Cell Culture

Zhiyentayev

Boltaev

Соловьева

et al. 2013

Photochem & Photobiology

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“…Downfield shifts of the DMG meso-proton resonances indicated disaggregation of the porphyrin that correlated with increased photoactivity. Moreover, it was concluded from PVP chemical shift changes (upfield shifts of all PVP resonances) that not just hydrophobic interactions, that were most pronounced, participated in the binding but also hydrophilic [ 166 , 167 ]. In another study, a series of six different porphyrin derivatives derived either from hematoporphyrin IX (HPIX) or PPIX was monitored with respect to PVP encapsulation by 1 H NMR spectroscopic analyses of the porphyrin resonances.…”

Section: Applications To Study Porphyrin–macromolecule Interactionmentioning

confidence: 99%

“…PEG is the most often encountered hydrophilic component of BCMs and in particular the triblock copolymers PEG-PPG-PEG, the so-called poloxamers or Pluronics (BASF trade name) [ 228 ], have been extensively explored as carriers for porphyrinic PSs [ 54 , 55 , 161 , 162 , 166 , 229 , 230 , 231 ]. BCM encapsulation is a strategy to enhance porphyrin delivery towards targeted tissue or profile the pharmacokinetics and pharmacodynamics of bioactive molecules.…”

Section: Applications To Study Porphyrin–macromolecule Interactionmentioning

confidence: 99%

“…The interaction of the hematoporphyrin derivative DMG [ 166 ] and Ce6 [ 161 ] with F127 ( Figure 11 ) Pluronic micelles or solely with PEG as homo-polymer was each probed by 1 H NMR spectroscopy. Both porphyrinic compounds exhibited disaggregation in the presence of the BCMs or PEG alone as was indicated by downfield shifts of the porphyrin/chlorin meso-proton, propionic acid and vinyl side chain protons, respectively.…”

Section: Applications To Study Porphyrin–macromolecule Interactionmentioning

confidence: 99%

“…Both compounds were suggested to localize preferentially in the hydrophobic core regions of the BCMs due to induced upfield shifts and partial broadening specifically of the F127-PPG resonances. However, disaggregation capability and observed upfield shifts of the PEG resonance in the case of mixing with the sole homo-polymer also proved a significant affinity of both DMG and Ce6 for the more hydrophilic PEG blocks so that a micellar location close to the PEG-PPG interface was suggested [ 161 , 166 ].…”

Section: Applications To Study Porphyrin–macromolecule Interactionmentioning

confidence: 99%

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Probing the Interactions of Porphyrins with Macromolecules Using NMR Spectroscopy Techniques

2021

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Porphyrinic compounds are widespread in nature and play key roles in biological processes such as oxygen transport in blood, enzymatic redox reactions or photosynthesis. In addition, both naturally derived as well as synthetic porphyrinic compounds are extensively explored for biomedical and technical applications such as photodynamic therapy (PDT) or photovoltaic systems, respectively. Their unique electronic structures and photophysical properties make this class of compounds so interesting for the multiple functions encountered. It is therefore not surprising that optical methods are typically the prevalent analytical tool applied in characterization and processes involving porphyrinic compounds. However, a wealth of complementary information can be obtained from NMR spectroscopic techniques. Based on the advantage of providing structural and dynamic information with atomic resolution simultaneously, NMR spectroscopy is a powerful method for studying molecular interactions between porphyrinic compounds and macromolecules. Such interactions are of special interest in medical applications of porphyrinic photosensitizers that are mostly combined with macromolecular carrier systems. The macromolecular surrounding typically stabilizes the encapsulated drug and may also modify its physical properties. Moreover, the interaction with macromolecular physiological components needs to be explored to understand and control mechanisms of action and therapeutic efficacy. This review focuses on such non-covalent interactions of porphyrinic drugs with synthetic polymers as well as with biomolecules such as phospholipids or proteins. A brief introduction into various NMR spectroscopic techniques is given including chemical shift perturbation methods, NOE enhancement spectroscopy, relaxation time measurements and diffusion-ordered spectroscopy. How these NMR tools are used to address porphyrin–macromolecule interactions with respect to their function in biomedical applications is the central point of the current review.

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Evaluation of polyvinylpyrrolidone and block copolymer micelle encapsulation of serine chlorin e6 and chlorin e4 on their reactivity towards albumin and transferrin and their cell uptake

Gjuroski

Girousi

Meyer

et al. 2019

Journal of Controlled Release

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Development of novel formulations for photodynamic therapy on the basis of amphiphilic polymers and porphyrin photosensitizers. Porphyrin-polymer complexes in model photosensitized processes

Cited by 21 publications

References 38 publications

Complexes of Chlorin e6 with Pluronics and Polyvinylpyrrolidone: Structure and Photodynamic Activity in Cell Culture

Complexes of Chlorin e6 with Pluronics and Polyvinylpyrrolidone: Structure and Photodynamic Activity in Cell Culture

Probing the Interactions of Porphyrins with Macromolecules Using NMR Spectroscopy Techniques

Evaluation of polyvinylpyrrolidone and block copolymer micelle encapsulation of serine chlorin e6 and chlorin e4 on their reactivity towards albumin and transferrin and their cell uptake

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