Asymmetric ZnPc–rhodamine B conjugates for mitochondrial targeted photodynamic therapy

Muli, Dominic K.; Rajaputra, Pallavi; You, Youngjae; McGrath, Dominic V.

doi:10.1016/j.bmcl.2014.07.082

Cited by 15 publications

(8 citation statements)

References 28 publications

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“…In our experiments, we show that, for the low ZnPcS 4 phthalocyanine concentration (c = 1 × 10 −6 M), the localization of the photosensitizer applies to mitochondria and lipid structures. This finding is consistent with the results proving that mono-or polysubstituted ZnPcs are mainly localized in the mitochondria and/or lysosomes in the Golgi apparatus, and, at a lower concentration, in the endoplasmic reticulum (ER) [67][68][69][70][71][72][73][74].…”

Section: Human Colon Cells After Adding Znpcssupporting

confidence: 92%

Zinc Phthalocyanine Photochemistry by Raman Imaging, Fluorescence Spectroscopy and Femtosecond Spectroscopy in Normal and Cancerous Human Colon Tissues and Single Cells

et al. 2020

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Photodynamic therapy is a clinically approved alternative method for cancer treatment in which a combination of nontoxic drugs known as photosensitizers and oxygen is used. Despite intensive investigations and encouraging results, zinc phthalocyanines (ZnPcs) have not yet been approved as photosensitizers for clinical use. Label-free Raman imaging of nonfixed and unstained normal and cancerous colon human tissues and normal human CCD18-Co and cancerous CaCo-2 cell lines, without and after adding ZnPcS4 photosensitizer, was analyzed. The biochemical composition of normal and cancerous colon tissues and colon cells without and after adding ZnPcS4 at the subcellular level was determined. Analyzing the fluorescence/Raman signals of ZnPcS4, we found that in normal human colon tissue samples, in contrast to cancerous ones, there is a lower affinity to ZnPcS4 phthalocyanine. Moreover, a higher concentration in cancerous tissue was concomitant with a blue shift of the maximum peak position specific for the photosensitizer from 691–695 nm to 689 nm. Simultaneously for both types of samples, the signal was observed in the monomer region, confirming the excellent properties of ZnPcS4 for photo therapy (PDT). For colon cell experiments with a lower concentration of ZnPcS4 photosensitizer, c = 1 × 10−6 M, the phthalocyanine was localized in mitochondria/lipid structures; for a higher concentration, c = 9 × 10−6 M, localization inside the nucleus was predominant. Based on time-resolved experiments, we found that ZnPcS4 in the presence of biological interfaces features longer excited-state lifetime photosensitizers compared to the aqueous solution and bare ZnPcS4 film on CaF2 substrate, which is beneficial for application in PDT.

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Section: Human Colon Cells After Adding Znpcssupporting

confidence: 92%

Zinc Phthalocyanine Photochemistry by Raman Imaging, Fluorescence Spectroscopy and Femtosecond Spectroscopy in Normal and Cancerous Human Colon Tissues and Single Cells

et al. 2020

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“…ammonium salt on the periphery, whereas Muli et al (2008), based on the properties of rhodamine B to target mitochondria, described the synthesis and characterization of asymmetric ZnPc-rhodamine B conjugates for selective mitochondrial targeting. Duan et al (2010) also showed a selective affinity to the mitochondria of a non-ionic 2-(dimethylamino)ethylthio ZnPc.…”

Section: Ros Formation Cellular Uptake and Intracellular Localizationmentioning

confidence: 99%

Zinc(II) phthalocyanines as photosensitizers for antitumor photodynamic therapy

Roguin

Chiarante

Vior

et al. 2019

The International Journal of Biochemistry & Cell Biology

109

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Photodynamic therapy (PDT) is a highly specific and clinically approved method for cancer treatment in which a nontoxic drug known as photosensitizer (PS) is administered to a patient. After selective tumor irradiation, an almost complete eradication of the tumor can be reached as a consequence of reactive oxygen species (ROS) generation, which not only damage tumor cells, but also lead to tumor-associated vasculature occlusion and the induction of an immune response. Despite exhaustive investigation and encouraging results, zinc(II) phthalocyanines (ZnPcs) have not been approved as PSs for clinical use yet. This review presents an overview on the physicochemical properties of ZnPcs and biological results obtained both in vitro and in more complex models, such as 3D cell cultures, chicken chorioallantoic membranes and tumor-bearing mice. Cell death pathways induced after PDT treatment with ZnPcs are discussed in each case. Finally, combined therapeutic strategies including ZnPcs and the currently available clinical trials are mentioned.

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“…[60] Hence, photosensitizers with high-Z elements can absorb more X-ray photons and lead to higher production of ROS. [61] Organic based X-PDT sensitizers. Organic photosensitizers own advantages of simple composition, tunable chemical structure and optical properties, good biocompatibility and facile functionalization.…”

Section: Photosensitizers Activated By X-raysmentioning

confidence: 99%

Recent Advances in Photosensitizer Materials for Light‐Mediated Tumor Therapy

Chen,

Zhu,

Zhang

et al. 2024

Chemistry An Asian Journal

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Photodynamic therapy (PDT) as an emerging therapeutic method has drawn many attentions in the treatment field for cancer. Photosensitizer, which can convert photon energy into cytotoxic species under light irradiation, is the core component in PDT. The design of photosensitizers still faces problems of light absorption, targeting, penetration and oxygen dependence. With the rapid progress of material science, various photosensitizers have been developed to produce cytotoxic species for treatment of tumor with high selectivity, safety, and noninvasiveness. Besides, the applications of photosensitizers have been expanded to diverse cancer treatments such as drug release, optogenetics and immune checkpoint blockade. In this review, we summarize the recent advances of photosensitizers in various therapeutic methods for cancer. Prevailing challenges and further prospects associated with photosensitizers are also discussed.

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Asymmetric ZnPc–rhodamine B conjugates for mitochondrial targeted photodynamic therapy

Cited by 15 publications

References 28 publications

Zinc Phthalocyanine Photochemistry by Raman Imaging, Fluorescence Spectroscopy and Femtosecond Spectroscopy in Normal and Cancerous Human Colon Tissues and Single Cells

Zinc Phthalocyanine Photochemistry by Raman Imaging, Fluorescence Spectroscopy and Femtosecond Spectroscopy in Normal and Cancerous Human Colon Tissues and Single Cells

Zinc(II) phthalocyanines as photosensitizers for antitumor photodynamic therapy

Recent Advances in Photosensitizer Materials for Light‐Mediated Tumor Therapy

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