Amphiphilic phthalocyanines in polymeric micelles: a supramolecular approach toward efficient third-generation photosensitizers

Setaro, Francesca; Wennink, J.W.H.; Mäkinen, Petri; Holappa, Lari; Trohopoulos, Panagiotis N.; Ylä‐Herttuala, Seppo; Nostrum, Cornelus F. van; Escosura, Andrés de la; Torres, Tomás

doi:10.1039/c9tb02014d

Cited by 41 publications

(34 citation statements)

References 42 publications

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“…Therefore, they have also been used as nanocarriers of PS. Very recently, Torres et al [ 40 ] reported PEG- b -PCL based micelles as carriers for a series of new third generation PS based on silicon phthalocyanine (SiPc) ( Scheme 8 ). The two target SiPc compounds bear two axial benzoyl substituents, each of them with either three methoxy(triethylenoxy) chains, or one with three methoxy(triethylenoxy) chains and one with three dodecyloxy chains ( Scheme 8 ).…”

Section: Phthalocyanine-polymeric Nanoparticle Delivery Systems For Cancer Photodynamic Therapymentioning

confidence: 99%

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Recent Progress in Phthalocyanine-Polymeric Nanoparticle Delivery Systems for Cancer Photodynamic Therapy

2021

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This perspective article summarizes the last decade’s developments in the field of phthalocyanine (Pc)-polymeric nanoparticle (NP) delivery systems for cancer photodynamic therapy (PDT), including studies with at least in vitro data. Moreover, special attention will be paid to the various strategies for enhancing the behavior of Pc-polymeric NPs in PDT, underlining the great potential of this class of nanomaterials as advanced Pcs’ nanocarriers for cancer PDT. This review shows that there is still a lot of research to be done, opening the door to new and interesting nanodelivery systems.

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Section: Phthalocyanine-polymeric Nanoparticle Delivery Systems For Cancer Photodynamic Therapymentioning

confidence: 99%

“… Schematic representation of the PEG- b -PCL based micelles as carriers for a series of new third generation PS based on SiPc (compounds 1 and 2 , while 3 serves as a reference lipophilic derivative) in PCL–PEG polymeric micelles. Reprinted with permission from ref [ 40 ]. Copyright 2020 The Royal Society of Chemistry.…”

Section: Schemes and Tablesmentioning

confidence: 99%

Recent Progress in Phthalocyanine-Polymeric Nanoparticle Delivery Systems for Cancer Photodynamic Therapy

2021

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“…Thus, the prepared NPs are potential as a single agent‐multifunctional theranostic nanoprobe for both PDT and fluorescence imaging. Setaro et al 45 reported on a novel supramolecular strategy to encapsulate Si(IV)Pc PSs in biodegradable polymeric NCs made of poly(e‐caprolactone)‐ b ‐methoxypoly(ethylene glycol) (PCL‐PEG) block copolymers. Si(IV)Pc compounds are amphiphilic, with hydrophobic core, whereas hydrophobicity increases along the series, making it possible to correlate the loading capacity in the polymeric capsules with the hydrophobic/hydrophilic balance of the Pc structure.…”

Section: Polymers For Delivery Of Pdt Pssmentioning

confidence: 99%

Polymers for enhanced photodynamic cancer therapy: Phthalocyanines as a photosensitzer model

Darwish

2020

Polymers for Advanced Techs

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The use of photosensitizers (PSs) in cancer therapy opened new avenues for developing minimally‐invasive treatment of cancer. However, problems related to lack of biocompatibility and tumor targeting of many photosensitizers limited their clinical use for many years. Tailor‐made polymeric nanoparticles can significantly enhance the biocompatibility of the photosensitizers, achieve high cellular internalization and prolonged blood circulation. Further, attachement of the photosensitizer to bifunctional polymeric chains can be used for building novel nano‐constructions such as combination therapy and image‐guided therapy. This review describes the innovations pertaining to polymeric drug delivery systems of laser‐based cancer therapeutics as disclosed in recent literature. Phthalocyanines were considered a model of photosensitizers and photodynamic therapy (PDT) as a model of phototherapy. Interestingly, these models are applicable to other biomedical photoreceptors such as porphyrins, Chlorin e6, gold nanoparticles, quantum dots, carbon dots, etc.

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“…This method simultaneously increases their application in targeted therapy whilst reducing their intrinsic toxicity [ 13 , 14 , 15 ]. The delivery agents tested to the greatest extent are liposomes [ 16 , 17 ], metal and metal oxide nanoparticles [ 18 , 19 , 20 ], and polymeric nanomaterials [ 21 ]. Various connections of porphyrinoids with nanoparticles and supramolecules have been studied so far.…”

Section: Introductionmentioning

confidence: 99%

Nipagin-Functionalized Porphyrazine and Phthalocyanine—Synthesis, Physicochemical Characterization and Toxicity Study after Deposition on Titanium Dioxide Nanoparticles P25

et al. 2021

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Aza-porphyrinoids exhibit distinct spectral properties in UV-Vis, and they are studied in applications such as photosensitizers in medicine and catalysts in technology. The use of appropriate peripheral substituents allows the modulation of their physicochemical properties. Phthalocyanine and sulfanyl porphyrazine octa-substituted with 4-(butoxycarbonyl)phenyloxy moieties were synthesized and characterized using UV-Vis and NMR spectroscopy, as well as mass spectrometry. A comparison of porphyrazine with phthalocyanine aza-porphyrinoids revealed that phthalocyanine macrocycle exhibits higher singlet oxygen generation quantum yields, reaching the value of 0.29 in DMF. After both macrocycles had been deposited on titanium dioxide nanoparticles P25, the cytotoxicities and photocytotoxicities of the prepared materials were studied using a Microtox® acute toxicity test. The highest cytotoxicity occurred after irradiation with a red light for the material composed of phthalocyanine deposited on titania nanoparticles.

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Amphiphilic phthalocyanines in polymeric micelles: a supramolecular approach toward efficient third-generation photosensitizers

Abstract: This article describes a straightforward supramolecular strategy to encapsulate amphiphilic silicon phthalocyanines in polymeric micelles. A member of this new series of third-generation photosensitizers presents promising PDT activity.

Cited by 41 publications

References 42 publications

Recent Progress in Phthalocyanine-Polymeric Nanoparticle Delivery Systems for Cancer Photodynamic Therapy

Recent Progress in Phthalocyanine-Polymeric Nanoparticle Delivery Systems for Cancer Photodynamic Therapy

Polymers for enhanced photodynamic cancer therapy: Phthalocyanines as a photosensitzer model

Nipagin-Functionalized Porphyrazine and Phthalocyanine—Synthesis, Physicochemical Characterization and Toxicity Study after Deposition on Titanium Dioxide Nanoparticles P25

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