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

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1398-1405 ◽  
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.

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.

Photophysical and photochemical properties of novel phthalocyanines bearing non-peripherally substituted mercaptoquinoline moiety

2012 ◽  
Vol 16 (07n08) ◽  
pp. 845-854 ◽  
Author(s):  
Göknur Yaşa ◽  
Ali Erdoğmuş ◽  
Ahmet Lütfi Uğur ◽  
M. Kasım Şener ◽  
Ulvi Avcıata ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Electronic Spectroscopy ◽  
Quantum Yields ◽  
Solubility In Water ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Good Solubility ◽  
Ft Ir ◽  
Photochemical Properties ◽  
First Time

The synthesis, photophysical and photochemical properties of nonperipherally (α) mercaptoquinoline substituted Zn(II) , TiO(IV) and Mg(II) and quaternized Zn(II) phthalocyanines are described for the first time. These complexes (2 to 5) and their precursor are characterized by elemental analysis, FT-IR, 1H NMR, electronic spectroscopy as well as mass spectroscopy. Complexes 2, 4 and 5 have good solubility in organic solvents such as CHCl3 , DCM, DMSO, DMF, THF and toluene and are not aggregated in all solvents within a wide concentration range. Complex 3 showed very good solubility in water as well as DMSO and DMF. General trends are described for singlet oxygen, photodegradation and fluorescence quantum yields of these complexes in DMSO and DMF. While complex 2 has higher singlet oxygen and fluorescence quantum yields than 3, 4 and 5, complex 4 has higher fluorescence quantum yields in DMF and DMSO than 2, 3 and 5. The effect of the solvents and metal on the photophysical and photochemical parameters of the metallophthalocyanines are also reported.

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.

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

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.

Water-soluble cyclometalated Ir(iii) complexes as carrier-free and pure nanoparticle photosensitizers for photodynamic therapy and cell imaging

2020 ◽  
Vol 49 (33) ◽  
pp. 11493-11497
Author(s):  
Xiaofan Tong ◽  
Liping Zhang ◽  
Lijuan Li ◽  
Yite Li ◽  
Zhiyu Yang ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Cell Imaging ◽  
Water Soluble ◽  
Carrier Free ◽  
First Time

A facile strategy to obtain water-soluble cyclometalated Ir(iii) complexes as carrier-free and pure nanoparticle photosensitizers for PDT and cell imaging is provided for the first time.

A zwitterionic red-emitting water-soluble conjugated polymer with high resistance to nonspecific binding for two-photon cell imaging and good singlet oxygen production capability

2021 ◽  
Author(s):  
Yan-Qin Huang ◽  
Shan-Shan Jiang ◽  
Li-Xiang Pan ◽  
Rui Zhang ◽  
Kun-Lin Liu ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Conjugated Polymers ◽  
Singlet Oxygen ◽  
High Resistance ◽  
Conjugated Polymer ◽  
Cell Imaging ◽  
Water Soluble ◽  
Oxygen Production ◽  
Nonspecific Binding ◽  
Two Photon

Water-soluble conjugated polymers (WSCPs) with dual capability of two-photon imaging and singlet oxygen (1O2) production have become one type of the most promising agents in noninvasive imaging guided 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.

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