Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines

Lima, Eurico; Boto, Renato E.; Ferreira, Diana P.; Fernandes, José R.; Ferreira, L. F. Vieira; Souto, Eliana B.; Silva, Amélia M.; Reis, Lucinda V.

doi:10.3390/ma13112646

Cited by 12 publications

(5 citation statements)

References 76 publications

(132 reference statements)

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“…In vitro phototoxicity of dyes was proven in breast cancer cell lines BT-474 (human ductal breast carcinoma) and MCF7 (human breast adenocarcinoma derived from pleural effusion) with reasonable IC 50 values (up to 0.6 μM). As an improvement, these dyes were found to be photostable, highlighting the stability of the zwitterionic dyes and improved the singlet oxygen quantum yields ( Lima et al, 2020 ).…”

Section: Cyanine Dyes In Phototherapiesmentioning

confidence: 99%

Recent Advances in Cyanine-Based Phototherapy Agents

et al. 2021

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Phototherapies, in the form of photodynamic therapy (PDT) and photothermal therapy (PTT), are very promising treatment modalities for cancer since they provide locality and turn-on mechanism for toxicity, both of which are critical in reducing off-site toxicity. Irradiation of photosensitive agents demonstrated successful therapeutic outcomes; however, each approach has its limitations and needs to be improved for clinical success. The combination of PTT and PDT may work in a synergistic way to overcome the limitations of each method and indeed improve the treatment efficacy. The development of single photosensitive agents capable of inducing both PDT and PTT is, therefore, extremely advantageous and highly desired. Cyanine dyes are shown to have such potential, hence have been very popular in the recent years. Luminescence of cyanine dyes renders them as phototheranostic molecules, reporting the localization of the photosensitive agent prior to irradiation to induce phototoxicity, hence allowing image-guided phototherapy. In this review, we mainly focus on the cyanine dye–based phototherapy of different cancer cells, concentrating on the advancements achieved in the last ten years.

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Section: Cyanine Dyes In Phototherapiesmentioning

confidence: 99%

Recent Advances in Cyanine-Based Phototherapy Agents

et al. 2021

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“…Photodynamic therapy involves the use of a photoactive molecule, light, and molecular oxygen present in tissues. When combined, these three compounds are capable of producing reactive oxygen species (ROS), which will induce target cell death [ 7 , 27 , 28 ]. Despite being a promising treatment, it has been used in a small number of patients, due to skin photosensitivity (the most common adverse effect) caused by systemically administered photosensitizers.…”

Section: Cancer Therapiesmentioning

confidence: 99%

Localized Therapeutic Approaches Based on Micro/Nanofibers for Cancer Treatment

et al. 2023

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Cancer remains one of the most challenging health problems worldwide, and localized therapeutic approaches based on micro/nanofibers have shown potential for its treatment. Micro/nanofibers offer several advantages as a drug delivery system, such as high surface area, tunable pore size, and sustained release properties, which can improve drug efficacy and reduce side effects. In addition, functionalization of these fibers with nanoparticles can enhance their targeting and therapeutic capabilities. Localized delivery of drugs and/or other therapeutic agents via micro/nanofibers can also help to overcome the limitations of systemic administration, such as poor bioavailability and off-target effects. Several studies have shown promising results in preclinical models of cancer, including inhibition of tumor growth and improved survival rates. However, more research is needed to overcome technical and regulatory challenges to bring these approaches to clinical use. Localized therapeutic approaches based on micro/nanofibers hold great promise for the future of cancer treatment, providing a targeted, effective, and minimally invasive alternative to traditional treatments. The main focus of this review is to explore the current treatments utilizing micro/nanofibers, as well as localized drug delivery systems that rely on fibrous structures to deliver and release drugs for the treatment of cancer in a specific area.

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“…Unfortunately, a complete comparison is not possible since the reported compounds show the same structure but different counterions (I − vs CF 3 SO 3 − ): the external heavy atom effect should increase the singlet oxygen quantum yield by about 20% [49]. An increase of cytotoxicity was recorded for symmetrical (4o-s) and asymmetrical benzoselenazole aminosquaraines (4t and 4u) [50,51]. They exhibited photodynamic activity against different human tumor cell lines, inhibiting cellular growth upon exposure to light mostly with GI 50 values less than 5 μM.…”

Section: Fig 2 Molecular Structures Of Squaraine 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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Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines

Cited by 12 publications

References 76 publications

Recent Advances in Cyanine-Based Phototherapy Agents

Recent Advances in Cyanine-Based Phototherapy Agents

Localized Therapeutic Approaches Based on Micro/Nanofibers for Cancer Treatment

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

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