Amphiphilic phthalocyanine–cyclodextrin conjugates for cancer photodynamic therapy

Lourenço, Leandro M. O.; Pereira, Patrícia M. R.; Maciel, Elisabete; Válega, Mónica; Domingues, M. Fátima; Domingues, M. Rosário M.; Neves, Maria G. P. M. S.; Cavaleiro, José A. S.; Fernandes, Rosa; Tomé, João P. C.

doi:10.1039/c4cc02226b

Cited by 84 publications

(54 citation statements)

References 27 publications

(25 reference statements)

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“…19) for cancer PDT. 116 Three such derivatives, Pc–α-CD, Pc–β-CD and Pc–γ-CD, were synthesized via nucleophilic substitution of cyclo-maltohexaose (α-CD), cyclo-maltoheptaose (β-CD) and cyclo-maltooctaose (γ-CD) on two fluorine atoms of PcF 16 . Then, they tested these compounds on the UM-UC-3 bladder cancer cell line for phototoxicity and the results revealed that Pc–α-CD and Pc–γ-CD exhibited higher phototoxi-city compared to Pc–β-CD.…”

Section: Substituted Fluorinated Porphyrinoids For Biological Applicamentioning

confidence: 99%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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Section: Substituted Fluorinated Porphyrinoids For Biological Applicamentioning

confidence: 99%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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“…24). All these results suggest that the higher phototoxicity of these compounds can be attributed to their higher cellular uptake and efficiency in generating intracellular ROS (Lourenço et al 2014).…”

Section: Cancer Pdt and Porphyrin-type Derivatives 1003mentioning

confidence: 81%

“…Having this in mind and in order to overcome the aggregation usually associated to these highly hydrophobic molecules, Lourenco et al reported in 2014 the synthesis of amphiphilic phatalocyanines (PCs) conjugated with α-, β-and γ-cyclodextrins as potential PSs for PDT (Lourenço et al 2014). Thus, Pc-α-CD 24, Pc-β-CD 25 and Pc-γ-CD 26 were synthesized by nucleophilic substitution of two fluorine atoms of PcF 16 (hexadecafluorophthalocyanine), a single substitution of a β-fluoro atom in one of the isoindole units followed by a second attack in another one of the adjacent isoindole unit, using, respectively, cyclo-maltohexaose (α-CD), cyclomaltoheptaose (β-CD) and cyclo-maltooctaose (γ-CD) (Fig.…”

Section: Cancer Pdt and Porphyrin-type Derivatives 1003mentioning

confidence: 99%

“…It takes into consideration the improvement mainly related with PS transport and specificity for tumors (Josefsen andBoyle 2008, Senge 2012). New or already known PSs are conjugated, for example, with antibodies (Kudarha and Sawant 2017, Hudson et al 2005, Pereira et al 2014 or nanoparticles (Yang et al 2017, Ma et al 2017). Targeting strategies have already shown that the PS affinity for tumors increases in significant ways.…”

Section: Development Of Photosensitizersmentioning

confidence: 99%

“…Thus, Pc-α-CD 24, Pc-β-CD 25 and Pc-γ-CD 26 were synthesized by nucleophilic substitution of two fluorine atoms of PcF 16 (hexadecafluorophthalocyanine), a single substitution of a β-fluoro atom in one of the isoindole units followed by a second attack in another one of the adjacent isoindole unit, using, respectively, cyclo-maltohexaose (α-CD), cyclomaltoheptaose (β-CD) and cyclo-maltooctaose (γ-CD) (Fig. 23) (Lourenço et al 2014).…”

Section: Cancer Pdt and Porphyrin-type Derivatives 1003mentioning

confidence: 99%

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Cancer, Photodynamic Therapy and Porphyrin-Type Derivatives

Gomes

Cavaleiro

2018

An. Acad. Bras. Ciênc.

105

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This review has two parts. The first one gives an approach to interdisciplinary studies against cancer carried out by many scientists using porphyrin-type substrates as photosensitizers in PDT. Intensive studies were performed for almost six decades. The successes really started in 1993 with the first formulation patented under the trade name Photofrin, which was immediately approved in several countries to treat certain types of cancer. Photofrin is still used although certain negative features soon became well known. That has motivated the search for better new photosensitizers. Several ones were developed, evaluated and a few of them had clinical approval. This group includes porphyrin derivatives and pro-drugs (aminolevulinic acid and its alkyl esters). Oncological, dermatological and ophthalmic applications are now taking place for the benefit of mankind. The second part of this review is related with the work carried out in Aveiro at the authors University on the synthesis and biological evaluation of several potential PDT photosensitizers. Not only new synthetic methodologies mainly for porphyrins and chlorins were developed but also other related macrocycles of the phthalocyanine and corrole types have entered in the same "pipeline". In vivo and in vitro biological evaluations also took place under interdisciplinary studies.

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Phthalocyanines and Porphyrazines

İşçi¹,

Dumoulin²

2022

Fundamentals of Porphyrin Chemistry

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Amphiphilic phthalocyanine–cyclodextrin conjugates for cancer photodynamic therapy

Cited by 84 publications

References 27 publications

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Cancer, Photodynamic Therapy and Porphyrin-Type Derivatives

Phthalocyanines and Porphyrazines

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