New A3B porphyrins as potential candidates for theranostic. Synthesis and photochemical behaviour

Boscencu, Rica; Socoteanu, Radu; Manda, Gina; Radulea, Natalia; Anastasescu, Mihai; Gama, Augusta; Machado, I. Ferreira; Ferreira, L. F. Vieira

doi:10.1016/j.dyepig.2018.08.028

Cited by 21 publications

(18 citation statements)

References 34 publications

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“…The detector is an indium gallium arsenide charged-coupled device (model iDus, Andor Technology Limited, Belfast, UK), working at (−60 • C), which was coupled to a fixed spectrograph. Further details regarding this technique can be found in reference [33]. By comparing the total area of the emission spectra for the reference compound (Phenazine in chloroform) and for each sample in the same solvent, the Φ ∆ values were obtained.…”

Section: Singlet Oxygen Formation Quantum Yields Determinationmentioning

confidence: 99%

“…Moreover, the evaluation of this photophysical parameter allows us to deduce the types of reaction produced by the photosensitizing molecules [11], since the triplet state of a photosensitizer, as generally stated in the introduction, can produce reactive oxygen species by two divergent mechanisms: type I reaction mechanism, in which the photosensitizer in the triplet state react with organic substrates to produce free radicals that interact with oxygen to generate, for example, superoxide radical anions, and a type II reaction mechanism, in which the triplet state energy is directly transferred to ground-state triplet oxygen to produce singlet oxygen [3,42]. This determination was performed in chloroform, and phenazine (singlet oxygen quantum yield of 0.84 [33,43]) was used as standard (Table 1). Due to the extremely reduced intensity of the phosphorescence emissions of singlet oxygen in common solvents, such as ethanol or acetonitrile, we were only able to record this emission in chloroform, despite the high sensitivity of the detector used.…”

Section: Solventmentioning

confidence: 99%

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Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects

et al. 2020

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Photodynamic therapy is a medical modality developed for the treatment of several diseases of oncological and non-oncological etiology that requires the presence of a photosensitizer, light and molecular oxygen, which combined will trigger physicochemical reactions responsible for reactive oxygen species production. Given the scarcity of photosensitizers that exhibit desirable characteristics for its potential application in this therapeutic strategy, the main aims of this work were the study of the photophysical and photochemical properties and the photobiological activity of several dicyanomethylene squaraine cyanine dyes. Thus, herein, the study of their aggregation character, photobleaching and singlet oxygen production ability, and the further application of the previously synthesized dyes in Caco-2 and HepG2 cancer cell lines, to evaluate their phototherapeutic effects, are described. Dicyanomethylene squaraine dyes exhibited moderate light-stability and, despite the low singlet oxygen quantum yields, were a core of dyes that exhibited relevant in vitro photodynamic activity, as there was an evident increase in the toxicity of some of the tested dyes exclusive to radiation treatments.

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Section: Singlet Oxygen Formation Quantum Yields Determinationmentioning

confidence: 99%

Section: Solventmentioning

confidence: 99%

Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects

et al. 2020

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“…Cationic porphyrins are currently the most explored porphyrins due to their capability to bind to a wider range of different structural moieties (Figure 5) and their ability to dissolve in aqueous solutions due to their amphiphilic nature [46]. Bio-application of cationic porphyrins is advantaged by the amphiphilic structure of cationic porphyrins which enables the hydrophilic end to allow drug administration by making it water soluble while the hydrophobic terminal facilitates cell entry and accumulation [47]. As highlighted earlier in this review, porphyrins have found use in a number of applications, these, however, are not limited to bio-applications.…”

Section: Porphyrins In Medicinal Imagingmentioning

confidence: 99%

Porphyrin as Diagnostic and Therapeutic Agent

2019

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The synthesis and application of porphyrins has seen a huge shift towards research in porphyrin bio-molecular based systems in the past decade. The preferential localization of porphyrins in tumors, as well as their ability to generate reactive singlet oxygen and low dark toxicities has resulted in their use in therapeutic applications such as photodynamic therapy. However, their inherent lack of bio-distribution due to water insolubility has shifted research into porphyrin-nanomaterial conjugated systems to address this challenge. This has broadened their bio-applications, viz. bio-sensors, fluorescence tracking, in vivo magnetic resonance imaging (MRI), and positron emission tomography (PET)/CT imaging to photo-immuno-therapy just to highlight a few. This paper reviews the unique theranostic role of porphyrins in disease diagnosis and therapy. The review highlights porphyrin conjugated systems and their applications. The review ends by bringing current challenges and future perspectives of porphyrin based conjugated systems and their respective applications into light.

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“…As shown in Scheme , both singlet‐singlet and triplet‐triplet energy transfer are in principle available. Indeed, metal‐free porphyrin‐based compounds usually show luminescence from both S 1 (fluorescence) and T 1 (phosphorescence) . These luminescence phenomena can be quenched if energy transfer takes place toward an acceptor chromophore.…”

Section: Introductionmentioning

confidence: 99%

Photosensitized Retinal Isomerization in Rhodopsin Mediated by a Triplet State

et al. 2019

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Direct 11-cis to all-trans retinal photoisomerization within rhodopsin is well known to be the initial chemical reaction triggering the process of vision in mammalians, such as bovine. Nevertheless, deep-sea fish are known to use chlorophyll derivatives as photosensitizers in order to see deep-red light, at wavelengths where retinal does not absorb. Also, some photodynamic therapy treatments were shown to enhance the vision of patients in dim light conditions. Energy transfer from the photosensitizer to rhodopsin was therefore proposed as a mechanism to populate the triplet state of the retinal chromophore. Herein, by means of hybrid quantum mechanicscoupled-molecular mechanics modeling techniques, we give insights into the possible energy mechanism and describe the retinal isomerization mediated by the lowest-lying triplet state. Especially, we show how a few kcal/mol energy barrier separates a T 1 minimum from a S 0 /T 1 intersection region, hence proposing an equilibrium between phosphorescence and isomerization processes. Moreover, the eventual self-production of singlet oxygen, constituting a potential danger for the integrity of rhodopsin, is discussed.

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New A3B porphyrins as potential candidates for theranostic. Synthesis and photochemical behaviour

Cited by 21 publications

References 34 publications

Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects

Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects

Porphyrin as Diagnostic and Therapeutic Agent

Photosensitized Retinal Isomerization in Rhodopsin Mediated by a Triplet State

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