Photodynamic effects induced by meso-tris(pentafluorophenyl)corrole and its cyclodextrin conjugates on cytoskeletal components of HeLa cells

Barata, Joana F. B.; Zamarrón, Alicia; Neves, Maria G. P. M. S.; Faustino, Maria A. F.; Tomé, Augusto C.; Cavaleiro, José A. S.; Röder, Beate; Juarranz, Ángeles; Sanz-Rodrı́guez, Francisco

doi:10.1016/j.ejmech.2014.12.025

Cited by 70 publications

(36 citation statements)

References 67 publications

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“…[3] This synthetic effort has been driven by the intriguingproperties of corrole, which can be schematized as "similar,b ut different" to the corresponding porphyrin counterparts. Both the synthetic availability and the peculiar properties have paved the way for interesting applications of such am acrocycle,i n fields rangingf rom catalysis, [4] clinical applications [5] to chemical sensors. [6] The functionalization of the macrocycle has ac ritical role to optimize the corrolefeatures for aspecific application.…”

Section: Introductionmentioning

confidence: 99%

A Highly Emissive Water‐Soluble Phosphorus Corrole

Naitana

Nardis

Pomarico

et al. 2016

Chemistry A European J

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The synthesis, spectroscopic, and optical properties of the water-soluble phosphorus complex of a 2-sulfonato-10-(4-sulfonatophenyl)-5,15-dimesitylcorrole have been investigated. The compound was prepared by adopting a novel strategy for the corrole sulfonation, leading to the regioselective isomer in an almost quantitative yield. The phosphorus coordination has a key role in determining the corrole substitution pattern, limiting the formation of poly-substituted species, which affected the reaction of the corrole free base. The resulting complex shows excellent optical properties in terms of emission quantum yield, also in polar protic solvents, including water. P NMR spectroscopy in CD OD indicates that the P sulfonate complex has been isolated in a hexacoordinated geometry with two different ligands (L1=-OH, L2=-OCH ), and it is prone to axial ligand exchange with methanol, with no evidence of intermediate pentacoordinated species. The morphological characterization of thin layers of the P corrole deposited onto an Au(111) surface showed that the addition of an intermediate layer of reduced graphene oxide allows for a better control of corrole aggregation, inducing also transformation of the Au(111) reconstructed surface.

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Section: Introductionmentioning

confidence: 99%

A Highly Emissive Water‐Soluble Phosphorus Corrole

Naitana

Nardis

Pomarico

et al. 2016

Chemistry A European J

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“…One or two units of β-CD have been linked to corrole, to evaluate the phototoxic effect in HeLa cells, with the generation of 1 O 2 for both conjugates. [113] A different interesting example is the linking of fluorinated chlorins to β-CD, showing good results of phototoxicity and a highwater solubility. [114] Regarding other carbohydrates, chitosan is a polysaccharide that comes from the deacetylation of chitin, which can be easily modified and shows interesting properties to be considered excellent nanomaterials for biomedical applications.…”

Section: Other Porphyrinoidsmentioning

confidence: 99%

Emerging Perspectives on Applications of Porphyrinoids for Photodynamic Therapy and Photoinactivation of Microorganisms

Almeida-Marrero¹,

González‐Delgado²,

Torres³

2019

MHC

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The use of photosensitizers (PSs) in photodynamic therapy (PDT) and photodynamic inactivation of microorganisms (PDI), as well in other biomedical techniques as medical imaging, represents a challenge for improving given properties that are desired in a biological media, such as water solubility, lack of aggregation and biocompatibility, among others. This review shows the most recent and important examples of the conjugation of photosensitizers to different biomolecules to achieve this goal. The manuscript is written in an accessible way in order to give a general vision of the recent advances stimulating at the same time the curiosity of the reader.

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“…Taking advantage of further optimized synthetic methodologies, 3 the scientific interest on corroles has continously increased, as witnessed by the abundance in the literature of accounts dealing with the theoretical 4 as well as more application-related aspects 5-8 and moving through chemical reactivity 9 and coordination ability of the corrole porphyrinoid. 10 …”

Section: Introductionmentioning

confidence: 99%

Corrole and nucleophilic aromatic substitution are not incompatible: a novel route to 2,3-difunctionalized copper corrolates

et al. 2015

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The insertion of a –NO2 group onto the corrole framework represents a key step for subsequent synthetic manipulation of the macrocycle based on the chemical versatility of such a functionality. Here we report results on the investigation of a copper 3-NO2-triarylcorrolate in nucleophilic aromatic substitution reactions with “active” methylene carbanions, namely diethyl malonate and diethyl 2-chloromalonate. Although similar reactions on nitroporphyrins afford chlorin derivatives, nucleophilic attack on carbon-2 of corrole produces 2,3-difunctionalized Cu corrolates in acceptable yields (ca. 30%), evidencing once again the erratic chemistry of this contracted porphyrinoid.

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Photodynamic effects induced by meso-tris(pentafluorophenyl)corrole and its cyclodextrin conjugates on cytoskeletal components of HeLa cells

Cited by 70 publications

References 67 publications

A Highly Emissive Water‐Soluble Phosphorus Corrole

A Highly Emissive Water‐Soluble Phosphorus Corrole

Emerging Perspectives on Applications of Porphyrinoids for Photodynamic Therapy and Photoinactivation of Microorganisms

Corrole and nucleophilic aromatic substitution are not incompatible: a novel route to 2,3-difunctionalized copper corrolates

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