Evaluation of Photodynamic Therapy Agents through Transient Grating Measurements

Beveridge, Andrew C.; Bench, Barbara A.; Gorun, Sergiu M.; Diebold, Gerald J.

doi:10.1021/jp022646e

Cited by 38 publications

(27 citation statements)

References 17 publications

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“…2a) produces 1 O 2 in a relatively high quantum yield232425. Unlike the protio phthalocyanine, H 16 PcZn, F 64 PcZn is stable in the presence of 1 O 2 and daughter, oxygen-centered species and other radicals2627.…”

Section: Resultsmentioning

confidence: 99%

Singlet oxygen-based electrosensing by molecular photosensitizers

et al. 2017

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Enzyme-based electrochemical biosensors are an inspiration for the development of (bio)analytical techniques. However, the instability and reproducibility of the reactivity of enzymes, combined with the need for chemical reagents for sensing remain challenges for the construction of useful devices. Here we present a sensing strategy inspired by the advantages of enzymes and photoelectrochemical sensing, namely the integration of aerobic photocatalysis and electrochemical analysis. The photosensitizer, a bioinspired perfluorinated Zn phthalocyanine, generates singlet-oxygen from air under visible light illumination and oxidizes analytes, yielding electrochemically-detectable products while resisting the oxidizing species it produces. Compared with enzymatic detection methods, the proposed strategy uses air instead of internally added reactive reagents, features intrinsic baseline correction via on/off light switching and shows C-F bonds-type enhanced stability. It also affords selectivity imparted by the catalytic process and nano-level detection, such as 20 nM amoxicillin in μl sample volumes.

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Section: Resultsmentioning

confidence: 99%

Singlet oxygen-based electrosensing by molecular photosensitizers

et al. 2017

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“…[20] Generally, the Φ F values of the studied fluorinated Znphthalocyanine complexes are higher than those of the nonfluorinated Zn-phthalocyanine complexes in DMSO. As described elsewhere, [36] the halogenation of the phthalocy-anine complexes on the phthalocyanine skeleton decreases the Φ F values. This observation is consistent with the notion that the aromatic fluorine groups are part of the phthalocyanine π system and thus increase the reactantproduct intersystem crossing.…”

Section: Fluorescence Lifetimes and Quantum Yieldsmentioning

confidence: 55%

Photophysical and Photochemical Properties of Fluorinated and Nonfluorinated n‐Propanol‐Substituted Zinc Phthalocyanines

2010

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The synthesis of symmetrical fluorinated and nonfluorinated zinc(II) phthalocyanine derivatives obtained from 4,5‐dichlorophthalonitrile, 4‐nitrophthalonitrile and 3‐nitrophthalonitrile substituted with 2,2,3,3‐tetrafluoro‐1‐propanol and n‐propanol are described. The comparison of the photophysicochemical properties of fluorinated and nonfluorinated substituted zinc(II) phthalocyanines is reported for the first time. The new compounds have been characterized by elemental analysis, IR, 1H NMR and 19F NMR spectroscopy, electronic spectroscopy and mass spectra. The photophysical and photochemical properties of the compounds were studied in dimethyl sulfoxide (DMSO). The complexes were quenched with benzoquinone (BQ), and their fluorescence‐quenching properties were investigated in the same solvent. The effects of the number of the substitution and the position on the photophysical and photochemical parameters of the zinc(II) phthalocyanines 1a–7a are also reported. Photophysical and photochemical properties of phthalocyanine complexes are very useful for photodynamic therapy (PDT) of cancer applications. In particular, high singlet‐oxygen quantum yields are very important for Type II mechanisms. These complexes have good singlet‐oxygen quantum yields and show potential as Type‐II photosensitizers.

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“…In the most of phthalocyanines, the Q band shifts to longer wavelengths with enlargement of π conjugated system. However, aliphatic fluorine groups in the complexes are not conjugated with the phthalocyanine p system [19]. That's why, these phthalocyanines showed less red shifting.…”

Section: Ground State Electronic Absorption Spectramentioning

confidence: 96%

Novel, Highle Soluble Non-Peripherally Phthalocyanines Bearing Bulky Groups Containing Fluorine Atoms: Synthesis, Characterization, Spectral and Improved Photophysicochemical Properties

Atmaca¹,

Erdoğmuş²

2017

HJBC

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Ö ZB u çalışmada yeni 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10 3-nitroftalonitril ve onun çözünebilir non-peripheral çinko (II) (2), magnezyum (II) (3), kobalt (II) (4) ve indiyum klorür (III) (5) ftalosiyanin türevlerinin sentezi ilk kez rapor edildi. Yeni sentezlenmiş metalo ftalosiyanin türevlerinin yapıları, kütle, UV-Vis, FT-IR, ve 1 H-NMR spektroskopisi kullanılarak karakterize edildi. Fotokimyasal (Singlet Oksijen foto bozunma kuantum verimleri) ve fotofiziksel (floresans kuantum verimleri) özellikleri tetrahidrofuran (THF) içinde incelendi. Flor atomları taşıyan uzun alkil zincirli gruplar taşıyan metallo fitalosiyaninlerin (2-5), THF, diklorometan (DCM), kloroform (CHCI 3 ) ve toluen gibi bilinen organik çözücülerde yığılma göstermeden yüksek çözünürlüğe sahip oldukları görüldü. Bunun yanı sıra, merkez metal iyon türü ve substitüentin pozisyon etkisi daha önceki çalışmalarla karşılaştırılarak çalışıldı. Non peripheral konumun fotofiziksel ve fotokimyasal özellikleri geliştirdiği gözlendi. Anahtar KelimelerFtalosiyaninler, fotofizik, fotokimya. A B S T R A C TT he synthesis of a new phthalonitrile (1) was described by treating 3-nitrophthalonitrile with 4- (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)phenol. After that, its soluble zinc(II) (2), magnesium(II) (3), cobalt(II) (4) and indium chloride(III) (5) non-peripheral phthalocyanine derivatives were reported for the first time. The newly synthesized metallo phthalocyanine derivatives were characterized by mass spectrometry, UV-Vis, FT-IR, and 1 H-NMR spectroscopy. Photochemical and photophysical (photodegradation, singlet oxygen and fluorescence quantum yields) properties of the phthalocyanines were carried out in tetrahydrofuran (THF). Metallo-phthalocyanines, which containing a bulky long alkyl chain bearing fluorine atoms, have high solubility in known organic solvents such as THF, dichloromethane (DCM), chloroform (CHCl 3 ) and toluene and do not show aggregation. Besides, the effect of metal ion types in phthalocyanines core (2, 3, 4 and 5) were also investigated. The effects of the substitution with fluoroalkynyl-functionalized groups on these parameters mentioned were also compared along with the previously synthesized peripherally tetra and octa substituted phthalocyanines. Non peripherally position of the substituents on Pc improved photophysical and photochemical properties.

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Evaluation of Photodynamic Therapy Agents through Transient Grating Measurements

Cited by 38 publications

References 17 publications

Singlet oxygen-based electrosensing by molecular photosensitizers

Singlet oxygen-based electrosensing by molecular photosensitizers

Photophysical and Photochemical Properties of Fluorinated and Nonfluorinated n‐Propanol‐Substituted Zinc Phthalocyanines

Novel, Highle Soluble Non-Peripherally Phthalocyanines Bearing Bulky Groups Containing Fluorine Atoms: Synthesis, Characterization, Spectral and Improved Photophysicochemical Properties

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