Nanoparticles of water-soluble dyads based on amino acid fullerene C60 derivatives and pyropheophorbide: Synthesis, photophysical properties, and photodynamic activity

Belik, A. Yu.; Rybkin, A. Yu.; Goryachev, N. S.; Sadkov, A. P.; Filatova, N. V.; Buyanovskaya, A. G.; Таланова, В. Н.; Klemenkova, Zinaida S.; Романова, В. С.; Koifman, Mikhail О.; Terentiev, Alexei A.; Котельников, А. И.

doi:10.1016/j.saa.2021.119885

Cited by 17 publications

(9 citation statements)

References 66 publications

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“…However, when a peptide linker was introduced between fulleropyrrolidin and the steroid moieties, significantly different supramolecular self‐aggregation was reported, 36 explained by the presence of hydrophilic peptide joined fulleropyrrolidine moiety and one steroid unit, but also related to the peptide segment flexibility, since with a short peptide as linker hierarchically self‐arranged branched network was observed, while increasing the size of peptide promote the formation of unordered, slightly curled sheets 36 . Besides, the self‐aggregation in an aqueous medium in fullerenes derivatives has also been described due to the association of hydrophobic C60 core 37 …”

Section: Resultsmentioning

confidence: 94%

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Morphological behavior of fullerene‐steroid hybrid derivatives

Lemos

Ortiz

Almagro

et al. 2022

Surface & Interface Analysis

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Over the years, fullerene has been covalently linked to other polar structures, increasing its aqueous solubility, thereby improving its potential use for biological and biomedical applications. Here, we report on the self‐organization characteristics in water of fullerene‐steroid hybrid derivatives with broad structural features. A library of 12 hybrid derivatives was prepared and classified into three groups: (1) mono adducts with only one steroid molecule and one fullerene moiety fused; (2) hybrids bearing wings with one fullerene moiety and two steroid molecules; and (3) a structure with two fullerene moieties linked to one steroid molecule and a mixture of two different monoaducts where C60‐malonate is attached to the A or D ring of steroid moiety. Different spectroscopic techniques characterized all synthesized fullerene derivatives, such as nuclear magnetic resonance (NMR) experiments (1H and 13C), Fourier transform infrared spectroscopy (FTIR), and high‐resolution mass spectrometry (HRMS). The morphology of the derivatives in aqueous solution was determined by transmission electron microscopy (TEM). In general, all the derivatives were organized into spherical nanoscale structures, where the structural characteristics defined the particle size distribution (PSD), showing a broad range of sizes from 6 to over 50 nm, and only a low percentage of larger particles were observed. The presence of dehydroepiandrosterone moieties in fullerene derivatives bearing wings and the increase in lipophilicity conferred by two C60 in the same structure induced more homogeneous and smaller particles, ranging from 6 to 20 nm. A preliminary computational study of the wing aggregates IIb showed that theoretical curve aggregates are more stable than linear ones supporting our TEM and PDS results.

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Section: Resultsmentioning

confidence: 94%

“…36 Besides, the self-aggregation in an aqueous medium in fullerenes derivatives has also been described due to the association of hydrophobic C60 core. 37 F I G U R E 5 Particle size distribution (PSD) of 400 nanoparticles of C 60 -steroid derivatives adsorbed on the TEM grids…”

Section: Psd Analysismentioning

confidence: 99%

Morphological behavior of fullerene‐steroid hybrid derivatives

Lemos

Ortiz

Almagro

et al. 2022

Surface & Interface Analysis

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“…Because of the oxygen-independent property of type I PDT, a variety of materials were designed and prepared to regulate the PDT mechanism and enhance type I PDT [ 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 ]. It is recognized that for the majority of photosensitizers, type I and II pathways typically exist simultaneously but competitively [ 48 , 49 , 50 , 51 ].…”

Section: Strategies For Modulating Tumor Hypoxia In Pdtmentioning

confidence: 99%

Recent Advances in Strategies for Addressing Hypoxia in Tumor Photodynamic Therapy

Liang

Luo

et al. 2022

Biomolecules

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Photodynamic therapy (PDT) is a treatment modality that uses light to target tumors and minimize damage to normal tissues. It offers advantages including high spatiotemporal selectivity, low side effects, and maximal preservation of tissue functions. However, the PDT efficiency is severely impeded by the hypoxic feature of tumors. Moreover, hypoxia may promote tumor metastasis and tumor resistance to multiple therapies. Therefore, addressing tumor hypoxia to improve PDT efficacy has been the focus of antitumor treatment, and research on this theme is continuously emerging. In this review, we summarize state-of-the-art advances in strategies for overcoming hypoxia in tumor PDTs, categorizing them into oxygen-independent phototherapy, oxygen-economizing PDT, and oxygen-supplementing PDT. Moreover, we highlight strategies possessing intriguing advantages such as exceedingly high PDT efficiency and high novelty, analyze the strengths and shortcomings of different methods, and envision the opportunities and challenges for future research.

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“…Also, primary and secondary amines seem able to undergo nucleophilic addition with C60 double bond. Romanova et al linked on fullerene amino groups belonging to different amino acids (Scheme 8C) by means of this approach [76,77]. Photolysis reaction is another method used for the synthesis of peptide-fullerenes derivatives [78].…”

Section: Scheme 7: Different Type Of [3+2] Cycloadditionmentioning

confidence: 99%