Synthesis and Encapsulation of a New Zinc Phthalocyanine Photosensitizer into Polymeric Nanoparticles to Enhance Cell Uptake and Phototoxicity

Mehraban, Nahid; Musich, Phillip R.; Freeman, Harold S.

doi:10.3390/app9030401

Cited by 19 publications

(10 citation statements)

References 29 publications

(32 reference statements)

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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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“…Among these parameters, MTT analysis (cell viability) is an effective and fast method used to determine cytotoxicity in vitro. In various studies using phthalocyanine, MTT analysis has been used to determine cytotoxicity (33,34). In present study as a result of MTT analysis for both cell lines, 12,8 µM concentration was determined as LD50 (Lethal Dose 50) that caused the death of half of the cells.…”

Section: Discussionmentioning

confidence: 96%

Anticancer activities of a metal-free phthalocyanine on MCF-7 and MDA-MB-231 cells and singlet oxygen production as a photosensitizer in PDT

Canlıca

Çeti̇n

2021

Journal of the Turkish Chemical Society Section A: Chemistry

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Cancer, which is often described as an uncontrollable rapid proliferation of cells, is currently the leading cause of death in the world together with cardiac disease. Therefore, the main purpose of the current research work was to study the anticancer effects of a first-time-synthesized phthalocyanine (Pc) as photosensitizer in PDT against cancer and evaluate its effects on human cells in vitro. Quantum yields of singlet oxygen photogeneration were in air using the relative method with standard-ZnPc as reference and DPBF as chemical quencher for singlet oxygen. The concentration of DPBF was prepared almost 3 x 10 -5 molar to avoid chain reactions induced by DPBF in the presence of singlet oxygen. Solutions of Pc as sensitizer (absorbance = 2.0 at the irradiation wavelength) containing DPBF were prepared in the dark and irradiated in the Q band region using the setup described. DPBF degradation at 417 nm was monitored with UV-Vis spectrophotometry. For in vitro studies, nine different MFPc-1 concentrations (0.2 µM-0.4 µM-0.8 µM-1.6 µM-3.2 µM-6.4 µM-12.8 µM-25.6 µM-51.2 µM) applied to MCF-7 and MDA-MB-231 breast cancer cell lines for 24 hours and MTT assay was carried out. After determination of optimum concentration, mitotic index, and apoptotic index values of cell lines were determined with administration of these concentrations. Singlet oxygen quantum yield (Φ), which is a measure of the efficiency, of MFPc-1 was found 0.50, although MFPc-1 is being metal-free phthalocyanine. For in vitro studies after the application of different concentrations to MCF-7 and MDA-MB-231 for 24 hours, the optimum concentration was determined as 12 µM for both cell lines by the MTT assay. After application of the determined optimum concentration for 24, 48 and 72 hours, there was a significant decrease in the mitotic index values and significant increase in the apoptotic index values of both MCF-7 and MDA-MB-231 breast cancer cell lines.

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“…Similarly, Mehraban et al [ 38 ] reported the use of PEG- b -PLGA-based nanocarriers to encapsulate new phthalocyanine derivatives. A new derivative of phthalocyanine was obtained by incorporating para-methylbenzyoxy groups in the β-positions of the ZnPc periphery (ZnPcBCH 3 , Scheme 6 ).…”

Section: Phthalocyanine-polymeric Nanoparticle Delivery Systems For Cancer Photodynamic Therapymentioning

confidence: 99%

Recent Progress in Phthalocyanine-Polymeric Nanoparticle Delivery Systems for Cancer Photodynamic Therapy

2021

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This perspective article summarizes the last decade’s developments in the field of phthalocyanine (Pc)-polymeric nanoparticle (NP) delivery systems for cancer photodynamic therapy (PDT), including studies with at least in vitro data. Moreover, special attention will be paid to the various strategies for enhancing the behavior of Pc-polymeric NPs in PDT, underlining the great potential of this class of nanomaterials as advanced Pcs’ nanocarriers for cancer PDT. This review shows that there is still a lot of research to be done, opening the door to new and interesting nanodelivery systems.

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Synthesis and Encapsulation of a New Zinc Phthalocyanine Photosensitizer into Polymeric Nanoparticles to Enhance Cell Uptake and Phototoxicity

Cited by 19 publications

References 29 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

Anticancer activities of a metal-free phthalocyanine on MCF-7 and MDA-MB-231 cells and singlet oxygen production as a photosensitizer in PDT

Recent Progress in Phthalocyanine-Polymeric Nanoparticle Delivery Systems for Cancer Photodynamic Therapy

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