Asymmetric ZnPc–TEG photosensitizers: the effect of Pc substitution on phototoxicity

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

doi:10.1016/j.tetlet.2015.09.101

Cited by 5 publications

(3 citation statements)

References 21 publications

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“…Thus, aggregates decrease not only the photoactivity of the PS but also limit the access to the neoplastic cells, affecting its bioavailability. The presence of bulky or electrically charged peripheral substituents bound to the macrocycle and/or axial ligands coordinated to the central metal minimizes the tendency to form aggregates (García Vior et al, 2009Muli et al, 2015). Ke et al (2009) demonstrated that tetra-αsubstituted ZnPcs exhibit a reduced aggregating trend, higher photostability and enhanced photocytotoxicity toward human gastric carcinoma cells than the tetra-β-substituted counterparts.…”

Section: Zinc(ii) Phthalocyanines For Pdtmentioning

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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Section: Zinc(ii) Phthalocyanines For Pdtmentioning

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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“…Other research groups have reported on pheophorbide and chlorin derivatives for efficient photosensitized eradication of tumor cells by alleviating solubility and aggregation problems. We and others have observed that polyethylene glycol (PEG) groups bonded to chlorophyll sensitizers can increase their solubility in solution, cell uptake, and phototoxicity in cancer cells. But previous work with chlorin e 6 had required chemically bonding each PEG group individually, with the third PEG adding in low yield (triPEG‐chlorin silica 2 and triPEG‐chlorin Teflon/PVA nanocomposite 3 , Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a poly(ethylene glycol) galloyl sensitizer tip for an ’all‐in‐one' photodynamic device

Ghogare

Greer

2016

Journal of Biophotonics

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This paper describes the synthesis of a specialized silica tip for an optical fiber device capable of delivering all components necessary for photodynamic therapy. Oxygen, light and a cleavable tripolyethylene glycol (PEG)-galloyl pheophorbide sensitizer are simultaneously delivered by the silica tip, where the tip was synthesized in six steps. A comparison of synthetic steps to reach PEGylated sensitizers bound to fluorinated silica and a previously reported Teflon/polyvinyl alcohol (PVA) nanocomposite ( Ghosh, G. et al. J. Phys. Chem. B 2015, 119, 4155- 4164) was made. The hydrolytic stability of the attached PEGs and the extent to which the PEG groups enhance solubility will also be discussed. The new triPEG-galloyl sensitizer has the potential for use in intraoperative pointsource photodynamic therapy which aims for precision treatment of residual disease. Schematic of the synthesis of a photoactive silica surface. It is composed of fluorinated silica connected to a photo-releasable sensitizer with short-chain PEGs.

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“…This may be because non-peripheral substitution shows more red-shifted absorption, as is the usual case for Pcs in the literature. 47,48 The metallo Pcs (1b and 2b) gave higher Φ Δ values than the metal-free Pcs (1a and 2a) because of the increase in the number of triple-state species by the central atom. 49 This observation could be in connection with the heavy metal effect of zinc which could induce intersystem crossing (ISC) and elicit the enhancement of singlet oxygen generation.…”

Section: Paper Dalton Transactionsmentioning

confidence: 99%