Synthesis of pH-Responsive Glycopolymer with End Group Zinc(II) Phthalocyanines as Potential Photosensitizer

A novel end-functionalized glycopolymer poly (3-O-methacryloyl-D-glucofuranose) -b-poly (2-Diethylaminoethyl Methacrylate) (PMAGlc-b-PDEA-ZnTAPc) with zinc (II) teraamaninophthalocyanine was synthesized. First, a pH-responsive copolymer PMAIpG-b-PDEA was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. Then PMAIpG-b-PDEA reacted with ZnTAPc and deprotected to form a water-soluble and pH-responsive photosensitizer. The structure of the PMAGlc-b-PDEA-ZnTAPc was characterized by 1H NMR and GPC. The photophysical properties were evaluated by UV-Vis and fluorescence spectra. The PMAGlc-b-PDEA-ZnTAPc can generate singlet oxygen species with good singlet oxygen quantum yields (Φ△=0.38), which is believed to be the major cytotoxic reactive oxygen species (ROS) for photodynamic therapy. The ZnPc functionalized glycopolymer will be used as a potential photosensitizer in the fields of photodynamic therapy.

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New peripherally substituted lutetium mono and bis phthalocyanines: Synthesis and comparative photophysical and photochemical properties

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424619501840 ◽

2019 ◽

Vol 23 (11n12) ◽

pp. 1542-1550

Author(s):

Nagihan Kocaağa ◽

Öznur Dülger Kutlu ◽

Ali Erdoğmuş

Keyword(s):

Mass Spectrometry ◽

Photodynamic Therapy ◽

Singlet Oxygen ◽

Photophysical Properties ◽

Quantum Yields ◽

Synthesis And Characterization ◽

Type Ii ◽

H Nmr ◽

Photochemical Properties

In this study, the synthesis and characterization of mono-(phthalocyaninato) lutetium(III) (1-Cl and 1-F) [Lu[Formula: see text](AcO)(Pc)] (Pc [Formula: see text] phthalocyaninato, AcO [Formula: see text] acetate) and bis-(phthalocyaninato) lutetium(III) (2-Cl and 2-Br) [Lu[Formula: see text]Pc[Formula: see text]] bearing halogenated (F, Cl and Br) phenoxy–phenoxy groups are described and verified by IR, [Formula: see text]H-NMR, UV-vis and mass spectrometry. Photochemical and photophysical properties of 1-F, 1-Cl 2-Cl and 2-Br in DMSO are also presented. A comparison between photophysical and photochemical parameters of mono and bis derivatives showed that mono phthalocyanines are better photosensitizers than bis phthalocyanines. Photophysical and photochemical properties of phthalocyanines are very useful for photodynamic therapy applications. Singlet oxygen quantum yields [Formula: see text] give an indication of the potential of the complexes as photosensitizers in photodynamic therapy applications. The chloro, fluoro, bromo-phenoxy–phenoxy substituted mono-(phthalocyaninato) lutetium(III) complexes (1-Cl and 1-F) gave good singlet oxygen quantum yields (from 0.86 to 0.80) in DMSO. Thus, these complexes show potential as Type II photosensitizers for PDT of cancer.

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Synthesis and Photophysical Properties of Tumor-Targeted Water-Soluble BODIPY Photosensitizers for Photodynamic Therapy

Molecules ◽

10.3390/molecules25153340 ◽

2020 ◽

Vol 25 (15) ◽

pp. 3340

Author(s):

Duy Khuong Mai ◽

Byungman Kang ◽

Temmy Pegarro Vales ◽

Isabel Wen Badon ◽

Sung Cho ◽

...

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Tumor Targeting ◽

Photophysical Properties ◽

Cancer Cell Lines ◽

Therapeutic Agents ◽

Water Soluble ◽

Oxygen Species ◽

Singlet Oxygen Species ◽

Mcf 7

The synthesis of three water-soluble lactose-modified 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based photosensitizers with tumor-targeting capabilities is reported, including an investigation into their photodynamic therapeutic activity on three distinct cancer cell lines (human hepatoma Huh7, cervical cancer HeLa, and breast cancer MCF-7 cell lines). The halogenated BODIPY dyes exhibited a decreased fluorescence quantum yield compared to their non-halogenated counterpart, and facilitated the efficient generation of singlet oxygen species. The synthesized dyes exhibited low cytotoxicities in the dark and high photodynamic therapeutic capabilities against the treated cancer cell lines following irradiation at 530 nm. Moreover, the incorporation of lactose moieties led to an enhanced cellular uptake of the BODIPY dyes. Collectively, the results presented herein provide promising insights for the development of photodynamic therapeutic agents for cancer treatment.

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Photophysical Properties of Pheophorbide-a Derivatives and Their Photodynamic Therapeutic Effects on a Tumor Cell LineIn Vitro

International Journal of Photoenergy ◽

10.1155/2014/793723 ◽

2014 ◽

Vol 2014 ◽

pp. 1-7 ◽

Cited By ~ 2

Author(s):

Kang-Kyun Wang ◽

Jing Li ◽

Bong-Jin Kim ◽

Jeong-Hyun Lee ◽

Hee-Won Shin ◽

...

Keyword(s):

Photodynamic Therapy ◽

Triplet State ◽

Singlet Oxygen ◽

Alkyl Group ◽

Photophysical Properties ◽

Hydroxyl Group ◽

Quantum Yields ◽

Therapeutic Effects ◽

Pheophorbide A

Pheophorbide-a derivatives have been reported to be potential photosensitizers for photodynamic therapy (PDT). In this study, photophysics of pheophorbide-a derivatives (PaDs) were investigated along with their photodynamic tumoricidal effectin vitro. PaDs were modified by changing the coil length and/or making the hydroxyl group (–OH) substitutions. Their photophysical properties were studied by steady-state and time-resolved spectroscopic methods. The photodynamic tumoricidal effect was evaluated in the mouse breast cancer cell line (EMT6). Lifetime and quantum yield of fluorescence and quantum yields of triplet state and singlet oxygen were studied to determine the dynamic energy flow. The coil length of the substituted alkyl group did not significantly affect the spectroscopic properties. However, the substitution with the hydroxyl group increased the quantum yields of the triplet state and the singlet oxygen due to the enhanced intersystem crossing. In order to check the application possibility as a photodynamic therapy agent, the PaDs with hydroxyl group were studied for the cellular affinity and the photodynamic tumoricidal effect of EMT6. The results showed that the cellular affinity and the photodynamic tumoricidal effect of PaDs with the hydroxyl group depended on the coil-length of the substituted alkyl group.

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Synthesis of new water soluble silicon phthalocyanine substituted by linker sulfur atom and photophysicochemical studies for photodynamic therapy

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424619501487 ◽

2019 ◽

Vol 23 (11n12) ◽

pp. 1398-1405 ◽

Cited By ~ 5

Author(s):

Göknur Yaşa Atmaca ◽

Ali Erdoğmuş

Keyword(s):

Photodynamic Therapy ◽

Singlet Oxygen ◽

Sulfur Atom ◽

Solvent Effects ◽

Water Soluble ◽

Quantum Yields ◽

Good Solubility ◽

Silicon Phthalocyanines ◽

First Time ◽

Soluble Silicon

In this work, 5-(trifluoromethyl)-2-thiopyridine substituted SiPc (1) and its quaternized derivative (2) were synthesized, and the effect of the linker sulfur atom on silicon phthalocyanines has been investigated for the first time in the literature. Both of the complexes have been characterized by standard spectroscopy methods. The complexes have good solubility in organic solvents and showed monomeric tendencies in all studied solvents. Only complex 2 had some aggregation in water because of solvent effects, as expected. In order to determine the therapeutic effect for cancer treatment, photophysicochemical properties were investigated in DMSO, DMF, toluene and water (for complex 2). The synthesized complexes were found to have about 3.5 times higher singlet oxygen quantum yields than the yields of unsubstituted SiPcCl2 ([Formula: see text] = 0.15 (in DMSO), 0.12 (in DMF), 0.10 (in toluene)) because of the effects of bulky axial groups.

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Symmetrically Substituted Zn and Al Phthalocyanines and Polymers for Photodynamic Therapy Application

Frontiers in Chemistry ◽

10.3389/fchem.2021.647331 ◽

2021 ◽

Vol 9 ◽

Author(s):

Keshavananda Prabhu C. P. ◽

Manjunatha Nemakal ◽

Muthumuni Managa ◽

Tebello Nyokong ◽

Lokesh Koodlur Sannegowda

Keyword(s):

Photodynamic Therapy ◽

Singlet Oxygen ◽

Clinical Response ◽

Macrocyclic Complexes ◽

Oxygen Species ◽

Early Biomarker ◽

Singlet Oxygen Species ◽

Mcf 7

N4 macrocyclic complexes of Al and Zn phthalocyanines with symmetrical imine and imidazole moiety at the periphery were synthesized. The synthesized ligands, complexes, and polymers were purified and characterized to study the structure of the molecule. These synthesized complexes were used for photodynamic therapy application as the diamagnetic Zn and Al have the ability to produce and stabilize singlet oxygen species. The synthesized N4 molecules of aluminum iminomethoxy phenyl phthalocyanine and aluminum ethyl phenyl benzimidazolephthalocyanine showed better activity against MCF-7 cells. These results suggest that this assay may be used as an early biomarker of clinical response.

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Modification of Gold Surfaces with Water-Soluble (Co)polymers Prepared via Aqueous Reversible Addition−Fragmentation Chain Transfer (RAFT) Polymerization†

Langmuir ◽

10.1021/la034459t ◽

2003 ◽

Vol 19 (14) ◽

pp. 5559-5562 ◽

Cited By ~ 133

Author(s):

Brent S. Sumerlin ◽

Andrew B. Lowe ◽

Paul A. Stroud ◽

Ping Zhang ◽

Marek W. Urban ◽

...

Keyword(s):

Chain Transfer ◽

Raft Polymerization ◽

Water Soluble ◽

Gold Surfaces ◽

Reversible Addition

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Singlet oxygen species and systemic lupus erythematosus: a brief review

Journal of Immunoassay and Immunochemistry ◽

10.1080/15321819.2019.1616555 ◽

2019 ◽

Vol 40 (4) ◽

pp. 343-349 ◽

Cited By ~ 2

Author(s):

Rizwan Ahmad ◽

Haseeb Ahsan

Keyword(s):

Systemic Lupus Erythematosus ◽

Singlet Oxygen ◽

Lupus Erythematosus ◽

Oxygen Species ◽

Systemic Lupus ◽

Singlet Oxygen Species

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Polythiophenes with Cationic Phosphonium Groups as Vectors for Imaging, siRNA Delivery, and Photodynamic Therapy

Nanomaterials ◽

10.3390/nano10081432 ◽

2020 ◽

Vol 10 (8) ◽

pp. 1432

Author(s):

Laure Lichon ◽

Clément Kotras ◽

Bauyrzhan Myrzakhmetov ◽

Philippe Arnoux ◽

Morgane Daurat ◽

...

Keyword(s):

Molecular Weight ◽

Photodynamic Therapy ◽

Photophysical Properties ◽

Combined Therapy ◽

Sirna Delivery ◽

Aqueous Media ◽

Low Molecular Weight ◽

Oxygen Species ◽

Cationic Polymers ◽

Intracellular Location

In this work, we exploit the versatile function of cationic phosphonium-conjugated polythiophenes to develop multifunctional platforms for imaging and combined therapy (siRNA delivery and photodynamic therapy). The photophysical properties (absorption, emission and light-induced generation of singlet oxygen) of these cationic polythiophenes were found to be sensitive to molecular weight. Upon light irradiation, low molecular weight cationic polythiophenes were able to light-sensitize surrounding oxygen into reactive oxygen species (ROS) while the highest were not due to its aggregation in aqueous media. These polymers are also fluorescent, allowing one to visualize their intracellular location through confocal microscopy. The most promising polymers were then used as vectors for siRNA delivery. Due to their cationic and amphipathic features, these polymers were found to effectively self-assemble with siRNA targeting the luciferase gene and deliver it in MDA-MB-231 cancer cells expressing luciferase, leading to 30–50% of the gene-silencing effect. In parallel, the photodynamic therapy (PDT) activity of these cationic polymers was restored after siRNA delivery, demonstrating their potential for combined PDT and gene therapy.

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Hydrogen Bond Acceptors and Additional Cationic Charges in Methylene Blue Derivatives: Photophysics and Antimicrobial Efficiency

BioMed Research International ◽

10.1155/2013/482167 ◽

2013 ◽

Vol 2013 ◽

pp. 1-12 ◽

Cited By ~ 22

Author(s):

Ariane Felgenträger ◽

Tim Maisch ◽

Daniel Dobler ◽

Andreas Späth

Keyword(s):

Methylene Blue ◽

Singlet Oxygen ◽

Direct Detection ◽

Photophysical Properties ◽

Red Light ◽

Quantum Yields ◽

Antimicrobial Efficiency ◽

Highly Active ◽

Light Region ◽

Multiresistant Bacteria

Photodynamic inactivation of bacteria (PIB) by efficient singlet oxygen photosensitizers might be a beneficial alternative to antibiotics in the struggle against multiresistant bacteria. Phenothiazinium dyes belong to the most prominent classes of such sensitizers due to their intense absorption in the red-light region ( ca. 600–680 nm, L mol−1 cm−1), their low toxicity, and their attachment/penetration abilities. Except simple substituents like alkyl or hydroxyalkyl residues, nearly no modifications of the phenothiaziniums have been pursued at the auxochromic sites. By this, the properties of methylene blue derivatives and their fields of application are limited; it remains unclear if their potential antimicrobial efficacy may be enhanced, also to compete with porphyrins. We prepared a set of six mainly novel methylene blue derivatives with the ability of additional hydrogen bonding and/or additional cationic charges to study the substituents’ effect on their activity/toxicity profiles and photophysical properties. Direct detection of singlet oxygen was performed at 1270 nm and the singlet oxygen quantum yields were determined. In suspensions with both, Gram-positive and Gram-negative bacteria, some derivatives were highly active upon illumination to inactivateS. aureusandE. coliup to 7 log10steps (99.99999%) without inherent toxicities in the nonirradiated state.

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