scholarly journals Singlet oxygen quantum yields from halogenated chlorins: potential new photodynamic therapy agents

2001 ◽  
Vol 138 (2) ◽  
pp. 147-157 ◽  
Author(s):  
Marta Pineiro ◽  
Mariette M Pereira ◽  
A.M.d’A Rocha Gonsalves ◽  
Luis G Arnaut ◽  
Sebastião J Formosinho
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Quantum Yields

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

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.

Bis-indole substituted phthalocyanines: Photophysical and photochemical properties

2020 ◽  
Vol 25 (01) ◽  
pp. 66-74
Author(s):  
Kevser Harmandar ◽  
Esra N. Kaya ◽  
Mehmet F. Saglam ◽  
Ibrahim F. Sengul ◽  
Devrim Atilla
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Spectral Data ◽  
Quantum Yields ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Singlet Oxygen Generation ◽  
Photochemical Properties ◽  
C Nmr

Tetra substituted peripheral and non-peripheral Zn(II) phthalocyanines were successfully synthesized employing 4-(bis(3-methyl-1H-indol-2-yl)methyl)phenol as a starting material. The structure of these synthesized compounds was confirmed using 1H NMR, [Formula: see text]C NMR, infrared (IR), UV-vis, and MALDI-TOF spectral data. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of all synthesized peripheral and non-peripheral compounds were investigated in order to determine the potential of these compounds for application in photodynamic therapy.

Quinolin-8-yloxy-substituted zinc(II) phthalocyanines for enhanced in vitro photodynamic therapy

2018 ◽  
Vol 22 (09n10) ◽  
pp. 807-813 ◽  
Author(s):  
Juanjuan Chen ◽  
Yuting Fang ◽  
Hong Liu ◽  
Naisheng Chen ◽  
Shengping Chen ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Clinical Application ◽  
Cellular Uptake ◽  
Culture Medium ◽  
Anticancer Agent ◽  
Quantum Yields ◽  
Anticancer Efficacy ◽  
Self Aggregation

Photodynamic therapy (PDT) is an innovative and promising modality to treat various tumors. In this study, two novel zinc(II) phthalocyanines substituted with quinolin-8-yloxy groups at the [Formula: see text]-position, namely mono(quinolin-8-yloxy) zinc(II) phthalocyanine (ZnPc-Q1) and tetra(quinolin-8-yloxy) zinc(II) phthalocyanine (ZnPc-Q4), have been synthesized and fully characterized. With quinolin-8-yloxy, these two phthalocyanines exhibit less self-aggregation in DMF and culture medium, high singlet oxygen quantum yields, mitochondria localization and high photodynamic activities (IC[Formula: see text] values as low as 2 nM). Compared to ZnPc-Q4, ZnPc-Q1 exhibits higher cellular uptake and lower IC[Formula: see text] values. Benefitting from its higher anticancer efficacy and lack of isomers, ZnPc-Q1 is a highly promising anticancer agent in clinical application.

scholarly journals Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

2019 ◽  
Vol 9 (24) ◽  
pp. 5414 ◽  
Author(s):  
Sofia Friães ◽  
Eurico Lima ◽  
Renato E. Boto ◽  
Diana Ferreira ◽  
José R. Fernandes ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Cell Lines ◽  
Light Emitting Diode ◽  
Cyanine Dyes ◽  
Quantum Yields ◽  
Light Emitting ◽  
Diode System ◽  
Hepg2 Cell Lines

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.

Photophysicochemical properties and photodynamic therapy activity of chloroindium(III) tetraarylporphyrins and their gold nanoparticle conjugates

2019 ◽  
Vol 23 (01n02) ◽  
pp. 34-45 ◽  
Author(s):  
Rodah C. Soy ◽  
Balaji Babu ◽  
David O. Oluwole ◽  
Njemuwa Nwaji ◽  
James Oyim ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
Dose Range ◽  
Heavy Atom ◽  
Therapeutic Window ◽  
Quantum Yields ◽  
Yield Values ◽  
Yield Formula

Novel chloroindium(III) complexes of tetra(4-methylthiophenyl)porphyrin (2a) and tetra-2-thienylporphyrin (2b) dyes have been synthesized and characterized. The main goal of the project was to identify fully symmetric porphyrin dyes with Q-band regions that lie partially in the therapeutic window that are suitable for use in photodynamic therapy (PDT). 2a and 2b were found to have fluorescence quantum yield values [Formula: see text] 0.01 and moderately high singlet oxygen quantum yields (0.54−0.73) due to heavy atom effects associated with the sulfur and indium atoms. The dark toxicity and PDT activity against epithelial breast cancer cells (MCF-7) were investigated over a dose range of 3.0−40 [Formula: see text]g [Formula: see text] mL[Formula: see text]. The in vitro dark cytotoxicity of 2a is significantly lower than that of 2b at [Formula: see text] 40 [Formula: see text]g [Formula: see text] mL[Formula: see text]. 2a was conjugated with gold nanoparticles (AuNPs) to form a nanoconjugate (2a-AuNPs), which exhibited a higher singlet oxygen quantum yield ([Formula: see text] value and PDT activity than was observed for 2a alone. The results suggest that the AuNPs nanoconjugates of readily synthesized fully symmetric porphyrin dyes are potentially suitable for PDT applications, if meso-aryl substituents that provide scope for nanoparticle conjugation can be introduced that shift the Q bands into the therapeutic window.

scholarly journals Photosensitizer synergistic effects: D–A–D structured organic molecule with enhanced fluorescence and singlet oxygen quantum yield for photodynamic therapy

2018 ◽  
Vol 9 (8) ◽  
pp. 2188-2194 ◽  
Author(s):  
Jianhua Zou ◽  
Zhihui Yin ◽  
Peng Wang ◽  
Dapeng Chen ◽  
Jinjun Shao ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
Cancer Diagnosis ◽  
Organic Molecule ◽  
Synergistic Effects ◽  
Quantum Yields ◽  
Enhanced Fluorescence ◽  
Strong Fluorescence

Novel photosensitizers have been developed with high 1O2 quantum yields and strong fluorescence for cancer diagnosis and PDT.

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

2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
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.

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

2020 ◽  
Vol 996 ◽  
pp. 82-87
Author(s):  
Shu Guo Dong ◽  
Gui Hua Cui ◽  
Qian Duan
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Raft Polymerization ◽  
Photophysical Properties ◽  
Water Soluble ◽  
Quantum Yields ◽  
Oxygen Species ◽  
Ph Responsive ◽  
Reversible Addition ◽  
Singlet Oxygen Species

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.

Desired properties of new phthalocyanines for photodynamic therapy

2011 ◽  
Vol 83 (9) ◽  
pp. 1763-1779 ◽  
Author(s):  
Tebello Nyokong
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Fluorescence Quantum Yield ◽  
Resonance Energy Transfer ◽  
Resonance Energy ◽  
Ring Expansion ◽  
Quantum Yields ◽  
Electromagnetic Spectrum ◽  
Central Metal ◽  
Triplet Quantum Yields

The manuscript focuses on the properties of phthalocyanines (Pcs) that are required for them to be employed as photosensitizers in applications such as photodynamic therapy (PDT). High triplet-state quantum yields and lifetimes as well as high singlet-oxygen quantum yields are required for a good photosensitizer. In addition, absorption of the photosensitizer in the red region of the electromagnetic spectrum is also required, and this can be achieved by ring expansion, substitution with electron-donating ligands, and change of the central metal among others. Quantum dots (QDs) are efficient accumulators of light energy, and they can transfer this energy to molecules that possess a very efficient ability to generate singlet oxygen through a process called Förster resonance energy transfer (FRET). Thus, there is a decrease in the fluorescence quantum yield of the QDs when in the vicinity of Pcs. Triplet quantum yields of the Pcs increase in the presence of QDs.

Synthesis and photophysicochemical properties of BODIPY dye functionalized gold nanorods for use in antimicrobial photodynamic therapy

2016 ◽  
Vol 20 (08n11) ◽  
pp. 1016-1024 ◽  
Author(s):  
Gugu Kubheka ◽  
Imran Uddin ◽  
Edith Amuhaya ◽  
John Mack ◽  
Tebello Nyokong
Keyword(s):  
Gold Nanoparticles ◽  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Gold Nanorods ◽  
Molecular Modelling ◽  
Quantum Yields ◽  
Antimicrobial Photodynamic Therapy ◽  
Boron Dipyrromethene

A series of boron dipyrromethene (BODIPY) dyes with properties that are ideal for a good photosensitizer have been prepared. Functionalization with bromine atoms and attachment to gold nanoparticles through a meso-aniline group results in high singlet oxygen quantum yields and low fluorescent quantum yields. Molecular modelling was used to analyze trends in the MO energies of various brominated aniline BODIPY dyes.

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