Novel water soluble 7-oxy-4-(pyridine-3-yl)coumarin substituted phthalocyanines as potential photosensitizers for photodynamic therapy

Boyar, Caner Yahya; Çamur, Meryem

doi:10.1016/j.ica.2019.05.004

Cited by 24 publications

(20 citation statements)

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“…Nevertheless, the search for new photosensitizers is also an active target for the development of PDT. Several works have reported the use of new compounds as promising photosensitizers [ 162 , 163 , 164 , 165 , 166 , 167 , 168 , 169 , 170 ]. From synthesized compounds based on previous structures to entirely new compounds, the research is in continuously update.…”

Section: Photodynamic Therapymentioning

confidence: 99%

Exploring the Applications of the Photoprotective Properties of Anthocyanins in Biological Systems

Oliveira

Correia

Pereira

et al. 2020

IJMS

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Due to their physical and chemical characteristics, anthocyanins are amongst the most versatile groups of natural compounds. Such unique signature makes these compounds a focus in several different areas of research. Anthocyanins have well been reported as bioactive compounds in a myriad of health disorders such as cardiovascular diseases, cancer, and obesity, among others, due to their anti-inflammatory, antioxidant, anti-diabetic, anti-bacterial, and anti-proliferative capacities. Such a vast number of action mechanisms may be also due to the number of structurally different anthocyanins plus their related derivatives. In this review, we highlight the recent advances on the potential use of anthocyanins in biological systems with particular focus on their photoprotective properties. Topics such as skin aging and eye degenerative diseases, highly influenced by light, and the action of anthocyanins against such damages will be discussed. Photodynamic Therapy and the potential role of anthocyanins as novel photosensitizers will be also a central theme of this review.

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Section: Photodynamic Therapymentioning

confidence: 99%

Exploring the Applications of the Photoprotective Properties of Anthocyanins in Biological Systems

Oliveira

Correia

Pereira

et al. 2020

IJMS

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“…The indium phthalocyanines ( 5 and 7 ) showed higher singlet oxygen production than the similar coumarin‐containing phthalocyanines in the literature. [ 46,50 ]…”

Section: Resultsmentioning

confidence: 99%

“…And also, the Φ F values for 4-7 were found lower than their counterparts containing different substituents on coumarin in the literature. [16,29,46,50] This can be due to more quenching of fluorescence via the substitution of the phthalocyanine compounds with two methyl groups located at 3 and 4 position on coumarin. It was observed that the Φ F values of zinc phthalocyanines (4 and 6) were higher than the indium phthalocyanines (5 and 7).…”

Section: Fluorescence Spectra Studiesmentioning

confidence: 99%

“…The indium phthalocyanines (5 and 7) showed higher singlet oxygen production than the similar coumarin-containing phthalocyanines in the literature. [46,50] UV-vis spectra of 4 for the investigation of singlet oxygen quantum yield (Φ Δ ) by chemical method using DPBF was given in Figure 9a as an example. Also, the decrease of DPBF absorbance at 417 nm for all compounds (4-7) during the singlet oxygen studies was given in Figure 9b.…”

Section: Singlet Oxygen Production Studiesmentioning

confidence: 99%

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Synthesis, characterization, and determination of photophysicochemical properties of peripheral and nonperipheral tetra‐7‐oxy‐3,4‐dimethylcoumarin substituted zinc, indium phthalocyanines

Artuç

Karapınar

Özdemir

et al. 2020

Applied Organom Chemis

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The photochemical and photophysical properties of peripheral and nonperipheral zinc and indium phthalocyanines containing 7-oxy-3,4-dimethylcoumarin synthesized were investigated in this study. 7-Hydroxy-3,4-dimethylcoumarin (1) was synthesized via Pechmann condensation reaction and then the phthalonitrile derivatives [4-(7-oxy-3,4-dimethylcoumarino)phthalonitrile (2) and 3-(7-oxy-3,-4-dimethylcoumarino)phthalonitrile (3)] were synthesized by nucleophilic aromatic substitution. Phthalocyanine compounds containing coumarin units on peripheral (4 and 5) and nonperipheral (6 and 7) positions were prepared via cyclotetramerization of phthalonitrile compounds. All compounds' characterizations were performed by spectroscopic methods and elemental analysis. The phthalocyanine derivatives' (4-7) photochemical and photophysical properties were studied in DMF. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties of these novel phthalocyanines (4-7) were studied in DMF. They produced good singlet oxygen (e.g., Φ Δ = 0.93 for 7) and showed appropriate photodegradation (in the order of 10 −5), which is very important for photodynamic therapy applications.

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“…Metal–phthalocyanine synthesis is key to improving the use of these complexes in PDT (Allison et al, 2004 ; Boyar and Çamur, 2019 ; Fujishiro et al, 2019 ). Among such complexes, ruthenium–phthalocyanine has emerged as a promising molecule because ruthenium complexes generally have octahedral geometry, and ruthenium–phthalocyanine is a hexacoordinated species that can still bind two new axial ligands (Heinrich et al, 2014 ; Teles Ferreira et al, 2017 ).…”

Section: Discussionmentioning

confidence: 99%

The Influence of Some Axial Ligands on Ruthenium–Phthalocyanine Complexes: Chemical, Photochemical, and Photobiological Properties

Martins

Negri

Pernomian

et al. 2021

Front. Mol. Biosci.

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This work presents a new procedure to synthesize ruthenium–phthalocyanine complexes and uses diverse spectroscopic techniques to characterize trans-[RuCl(Pc)DMSO] (I) (Pc = phthalocyanine) and trans-[Ru(Pc)(4-ampy)2] (II) (4-ampy = 4-aminopyridine). The triplet excited-state lifetimes of (I) measured by nanosecond transient absorption showed that two processes occurred, one around 15 ns and the other around 3.8 μs. Axial ligands seemed to affect the singlet oxygen quantum yield. Yields of 0.62 and 0.14 were achieved for (I) and (II), respectively. The lower value obtained for (II) probably resulted from secondary reactions of singlet oxygen in the presence of the ruthenium complex. We also investigate how axial ligands in the ruthenium–phthalocyanine complexes affect their photo-bioactivity in B16F10 murine melanoma cells. In the case of (I) at 1 μmol/L, photosensitization with 5.95 J/cm2 provided B16F10 cell viability of 6%, showing that (I) was more active than (II) at the same concentration. Furthermore, (II) was detected intracellularly in B16F10 cell extracts. The behavior of the evaluated ruthenium–phthalocyanine complexes point to the potential use of (I) as a metal-based drug in clinical therapy. Changes in axial ligands can modulate the photosensitizer activity of the ruthenium phthalocyanine complexes.

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Novel water soluble 7-oxy-4-(pyridine-3-yl)coumarin substituted phthalocyanines as potential photosensitizers for photodynamic therapy

Cited by 24 publications

References 50 publications

Exploring the Applications of the Photoprotective Properties of Anthocyanins in Biological Systems

Exploring the Applications of the Photoprotective Properties of Anthocyanins in Biological Systems

Synthesis, characterization, and determination of photophysicochemical properties of peripheral and nonperipheral tetra‐7‐oxy‐3,4‐dimethylcoumarin substituted zinc, indium phthalocyanines

The Influence of Some Axial Ligands on Ruthenium–Phthalocyanine Complexes: Chemical, Photochemical, and Photobiological Properties

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