Design and synthesis of symmetrical pentamethine cyanine dyes as NIR photosensitizers for PDT

Ciubini, Betty; Visentin, Sonja; Serpe, Loredana; Canaparo, Roberto; Fin, Andréa; Barbero, Nadia

doi:10.1016/j.dyepig.2018.09.009

Cited by 58 publications

(26 citation statements)

References 31 publications

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“…Although some PDT photosensitizers are already commercially available, mostly derived from porphyrins, these light-sensitive molecules have the disadvantage of being slowly eliminated from the body, causing skin photosensitivity [8,39]. Thus, several research studies have recently reported the discovery of new compounds, such as cyanines [40], squaraines [24], chlorins [41] or phthalocyanines [42] which, by appropriate structural modifications, can ideally override the gaps of first-generation photosensitizers [43].…”

Section: Introductionmentioning

confidence: 99%

Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

et al. 2019

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The search to replace conventional cancer treatment therapies, such as chemotherapy, radiotherapy and surgery has led over the last ten years, to a substantial effort in the development of several classes of photodynamic therapy photosensitizers with desired photophysicochemical and photobiological properties.Herein we report the synthesis of 6-iodoquinoline-and benzothiazole-based unsymmetrical squaraine cyanine dyes functionalized with amine groups located in the four-membered central ring. Their photodegradation and singlet oxygen production ability, as well as their in vitro photocytotoxicity against Caco-2 and HepG2 cell lines using a 630.8 ± 0.8 nm centered light-emitting diode system, were also investigated. All photosensitizer candidates displayed strong absorption within the tissue transparency spectral region (650-850 nm). The synthesized dyes were found to have moderate light stability. The potential of these compounds is evidenced by their cytotoxic activity against both tumor cell lines, highlighting the zwitterionic unsubstituted dye, which showed more intense photodynamic activity. Although the singlet oxygen quantum yields of these iodinated derivatives are considered low, it could be concluded that their introduction into the quinoline heterocycle was highly advantageous as it played a role in increasing selective cytotoxicity in the presence of light. Thus, the novel synthesized dyes present photophysicochemical and in vitro photobiological properties that make them excellent photosensitizer candidates for photodynamic therapy.

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Section: Introductionmentioning

confidence: 99%

Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

et al. 2019

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“…It has a high photoluminescence quantum yield (PLQY) of 47%, which makes this class of cyanine dyes also attractive for NIR fluorescent labeling. 54 − 56 …”

Section: Results and Discussionmentioning

confidence: 99%

Transparent and Colorless Dye-Sensitized Solar Cells Exceeding 75% Average Visible Transmittance

Naim

Novelli

Nikolinakos

et al. 2021

JACS Au

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100

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Most photovoltaic (PV) technologies are opaque to maximize visible light absorption. However, see-through solar cells open additional perspectives for PV integration. Looking beyond maximizing visible light harvesting, this work considers the human eye photopic response to optimize a selective near-infrared sensitizer based on a polymethine cyanine structure (VG20-C x ) to render dye-sensitized solar cells (DSSCs) fully transparent and colorless. This peculiarity was achieved by conferring to the dye the ability to strongly and sharply absorb beyond 800 nm (S 0 –S 1 transition) while rejecting the upper S 0 –S n contributions far in the blue where the human retina is poorly sensitive. When associated with an aggregation-free anatase TiO 2 photoanode, the selective NIR-DSSC can display 3.1% power conversion efficiency, up to 76% average visible transmittance (AVT), a value approaching the 78% AVT value of a standard double glazing window while reaching a color rendering index (CRI) of 92.1%. The ultrafast and fast charge transfer processes are herein discussed, clarifying the different relaxation channels from the dye monomer excited states and highlighting the limiting steps to provide future directions to enhance the performances of this nonintrusive NIR-DSSC technology.

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“…Among these three dyes, the Br-substituted one was able to enhance the singlet oxygen quantum yield showing a better half maxima Inhibitory Concentration IC 50 and higher phototoxicity against MCF-7 cells with mitochondria localization. Our group reported a series of symmetrical Cy5 based on the benzoindolenine ring with different substitutions: bromine and C2 or C4 alkyl chains (5d-g) [60]. These PSs have an absorption slightly more shifted toward the NIR (680-699 nm) with phototoxicity at very low concentration (10 nM).…”

Section: Pentamethine Cyanine Dyesmentioning

confidence: 99%

Polymethine dyes for PDT: recent advances and perspectives to drive future applications

Dereje

Pontremoli

Plata

et al. 2022

Photochem Photobiol Sci

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It has been proved that the effectiveness of photodynamic therapy (PDT) is closely related to the intrinsic features of the photosensitizer (PS). Over the recent years, several efforts have been devoted to the discovery of novel and more efficient photosensitizers showing higher efficacy and lower side effects. In this context, squaraine and cyanine dyes have been reported to potentially overcome the drawbacks related to the traditional PSs. In fact, squaraines and cyanines are characterized by sharp and intense absorption bands and narrow emission bands with high extinction coefficients typically in the red and near-infrared region, good photo and thermal stability and a strong fluorescent emission in organic solvents. In addition, biocompatibility and low toxicity make them suitable for biological applications. Despite these interesting intrinsic features, their chemical instability and self-aggregation properties in biological media still limit their use in PDT. To overcome these drawbacks, the self-assembly and incorporation into smart nanoparticle systems are forwarded promising approaches that can control their physicochemical properties, providing rational solutions for the limitation of free dye administration in the PDT application. The present review summarizes the latest advances in squaraine and cyanine dyes for PDT application, analyzing the different strategies, i.e.the self-assembly and the incorporation into nanoparticles, to further enhance their photochemical properties and therapeutic potential. The in vivo assessments are still limited, thus further delaying their effective application in PDT. Graphical abstract

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Design and synthesis of symmetrical pentamethine cyanine dyes as NIR photosensitizers for PDT

Cited by 58 publications

References 31 publications

Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

Transparent and Colorless Dye-Sensitized Solar Cells Exceeding 75% Average Visible Transmittance

Polymethine dyes for PDT: recent advances and perspectives to drive future applications

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