Novel lutetium(III) phthalocyanine-coumarin dyads; synthesis, characterization, photochemical, theoretical and antioxidant properties

Özdemir, Mücahit; Köksoy, Baybars; Yalçın, Bahattin; Taşkın, Turgut; Selçuki, Nursel Açar; Salan, Ümit; Durmuş, Mahmut; Bulut, Mustafa

doi:10.1016/j.ica.2020.120145

Cited by 16 publications

(15 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another example of promising antioxidants represents synthesized in 2020 by Özdemir et al novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted lutetium (III) phthalocyanine compounds ( Özdemir and Kӧksoy., 2020 ). The radical cation scavenging activities of complexes 36 and 37 (120.344 mM trolox/mg and 188.733 mM trolox/mg, respectively) ( Table 1 ) were significantly higher than the values for standard BHA - butylated hydroxyanisole (52.63 mM trolox/mg) in 2,2′-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) analysis.…”

Section: Antioxidant Complexesmentioning

confidence: 99%

“…In 2020, Özdemir and co-workers exploited the copper(I)-catalyzed azide-alkyne Huisgen 1,3-dipolar cycloaddition reaction to obtain the first example of phthalocyanine-coumarin derivatives bearing triazole ring, which constitute the direct precursors of peripheral 38–39 or non-peripheral 40–41 zinc(II) and magnesium (II) phthalocyanines (Zn-Pcs or Mg-Pcs) ( Table 1 ) ( Özdemir and Kӧksoy., 2020 ). The photophysical and photochemical studies revealed that complexes 38–41 may be used as type II photosensitizers in photodynamic therapy because the singlet oxygen quantum yields (Φ Δ ) ranged in acceptable values from 0.17 to 0.49; the highest Φ Δ value was observed for the peripheral zinc phthalocyanine 38 (Φ Δ = 0.489 in DMSO).…”

Section: Complexes As Photosensitizers In Photodynamic Therapymentioning

confidence: 99%

See 1 more Smart Citation

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

et al. 2021

View full text Add to dashboard Cite

The coumarin nucleus is a recurring motif in both natural and synthetic compounds that exhibit a broad spectrum of biological properties including anticoagulant, anti-inflammatory, antioxidant, antiviral, antimicrobial and anticancer agents as well as enzyme inhibitors. On the other hand, it has been reported that the incorporation of a metal ion into coumarin derivatives can increase the activity of such complexes compared to coumarin-based ligands. Accordingly, some of them have been found to display promising antioxidant, antitumor or antibacterial activities. This mini-review briefly summarizes the recent development of coumarin-metal complexes with proven biological properties. The attention is also paid to agents for which practical applications in the detection of biologically important species may be found.

show abstract

Section: Antioxidant Complexesmentioning

confidence: 99%

Section: Complexes As Photosensitizers In Photodynamic Therapymentioning

confidence: 99%

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Due to these structural properties, it is used in many fields such as non‐linear optics, [4] pigments, [5] solar cells, [6–7] catalyst, [8–9] gas sensors, [10] liquid crystal [11] . In addition, it continues to be the subject of intense research for medical purposes such as antioxidant, antimicrobial, pharmacology, photosensitizer for photodynamic therapy [12–14] . Fluorescence properties and singlet oxygen production capacity are the most sought‐after properties of compounds, especially for photodynamic therapy.…”

Section: Introductionmentioning

confidence: 99%

“…[11] In addition, it continues to be the subject of intense research for medical purposes such as antioxidant, antimicrobial, pharmacology, photosensitizer for photodynamic therapy. [12][13][14] Fluorescence properties and singlet oxygen production capacity are the most sought-after properties of compounds, especially for photodynamic therapy. For this reason, in this study, the synthesis of axial phthalocyanines known for their fluorescent properties was aimed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Axial Bis(benzo[d][1,3]dioxol‐5‐ylmethoxy)phthalocyaninato Silicon (IV): Photophysical and Photochemical Properties and Docking Studies on DNA‐SiPc Interactions

2022

View full text Add to dashboard Cite

The synthesis of an axial phthalocyanine compound by the reaction of piperonyl alcohol and SiPcCl2 has been reported. Its structure was characterized by compound 1HNMR,13CNMR, Mass, FTIR and UV visible spectroscopy. Photophysical and photochemical properties of the compound were investigated by fluorescence spectroscopy. The photosensitizer performance of the compound was determined. In addition, with the quantum chemical study, the HOMO ‐ LUMO band gap and the optimized structure of the compound were investigated with two basic sets of the TD‐DFT B3LYP method. The band gap (ΔE) was found to be in the range of 0.6–0.7 eV, and it was determined that the compound would require low energy in the chemotherapeutic interaction with light and in its stimulation. As a chemotherapy drug candidate, its adhesion to protein and DNA structure has been evaluated as in‐silico. In this context, the potential binding and interaction aspects of the new chemotherapeutically effective phthalocyanine compound with two kinds of homo sapiens protein‐DNA complexes were investigated by molecular docking approach. It bonded with the phthalocyanine compound in both crystal structures. A docking score of 6.315 kcal/mol was obtained in the 6DIA encoded DNA polymerase beta substrate complex.

show abstract

“…Phthalocyanines are widely used in many areas of activity, such as catalysis [ 1 , 2 ], light industry [ 3 , 4 ], medicine [ 5 , 6 ], linear and nonlinear optics and energy storage devices [ 7 , 8 , 9 ]. Such a widespread usage is associated with the high stability of these molecules, the presence of intense light absorption in the visible range, the flexibility of the design of structures [ 10 , 11 , 12 ], the possibility of introducing practically any metal atom into the central cavity [ 13 , 14 , 15 ] and the possession of significant coordination properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Properties and Redox Behavior Kinetics of Rare-Earth Bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato Metal Complexes with Er, Lu and Yb

et al. 2021

View full text Add to dashboard Cite

Novel bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato of complexes erbium, lutetium and ytterbium were synthesized using a template fusion method to prevent any polymerization process. The complexes were separated from the reaction mixtures and characterized by NMR, IR and electron absorption spectroscopy. The spectroscopic properties of the metal phthalocyaninates in chloroform, acetone and tetrahydrofuran were studied. The regular bathochromic shift in the Er–Yb–Lu series was determined. In acetone medium all the complexes obtained were found to exist in an equilibrium state between neutral and reduced forms. The linearity of Lambert-Bouger-Beer curves makes it possible to study the kinetics of redox processes in the presence of phenylhydrazine and bromine. The lutetium complex showed better reducing properties and turned fully into the reduced form, while the erbium and ytterbium ones changed only partially. Upon oxidizing all the phthalocyaninates transformed into a mixture of oxidized and neutral-radical forms. The extinction coefficients and effective redox constants were calculated.

show abstract

Novel lutetium(III) phthalocyanine-coumarin dyads; synthesis, characterization, photochemical, theoretical and antioxidant properties

Cited by 16 publications

References 42 publications

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

Synthesis of Axial Bis(benzo[d][1,3]dioxol‐5‐ylmethoxy)phthalocyaninato Silicon (IV): Photophysical and Photochemical Properties and Docking Studies on DNA‐SiPc Interactions

Synthesis, Spectroscopic Properties and Redox Behavior Kinetics of Rare-Earth Bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato Metal Complexes with Er, Lu and Yb

Contact Info

Product

Resources

About