In vitro photodynamic activities of zinc(II) phthalocyanines substituted with pyridine moieties

Liu, Jianyong; Li, Jun; Yuan, Xingliang; Wang, Wanming; Xue, Jinping

doi:10.1016/j.pdpdt.2015.07.003

Cited by 21 publications

(7 citation statements)

References 6 publications

(5 reference statements)

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“…Consequently, the photodynamic activity will greatly reduce, even disappear due to aggregation. 18 The interaction of CuPc with G-quadruplex DNA prevented the aggregation of CuPc molecules.…”

Section: Uv-vis Spectroscopymentioning

confidence: 99%

Thermodynamic and structural investigation of the interaction of quaternized 2,3‐octakis‐[(2‐mercaptopyridine)phthalocyaninato] copper (II) sulfate (CuPc) with parallel and hybrid type G‐quadruplex

Şahin,

Bağda,

Göktuğ Temiz

et al. 2023

J of Molecular Recognition

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G‐quadruplexes are important drug targets and get attention due to their existence in telomere, ribosomal DNA, promoter regions of some oncogenes, and the untranslated regions of mRNA. Due to the biological roles of G‐quadruplexes, investigating of the G‐quadruplex–small molecule interaction is essential. The primary motivation for these studies is the possibility of inhibiting cell functions associated with G‐quadruplex sequences by binding with small molecules. Targeting the small molecules to desired tissue with the G‐quadruplex vehicles is the second important goal of the G‐quadruplex–small molecule interaction studies. In the present study, the new peripherally 2‐mercaptopyridine octasubstituted copper(II) phthalocyanine and its quaternized derivative (CuPc) were synthesized and characterized by elemental analysis FT‐IR, UV–Vis, and mass spectra. The excellent solubility of CuPc in water is essential for its transport in the organism. Because of this feature, its affinity toward G‐quadruplex forming aptamers, AS1411, Tel21, and Tel45, was investigated. The UV–Vis spectrophotometric titration data confirmed the prevention of aggregation upon interaction with G‐quadruplex, which is very important for biomedical applications. The CD spectroscopic analyses and binding stoichiometry confirmed the “end stacking” model for interaction of AS1411 with CuPc. The interaction of CuPc caused the equilibrium shift from hybrid conformation to antiparallel conformation for Tel21 and Tel45. The isothermal titration calorimeter (ITC) was used for the determination of thermodynamic parameters. The thermodynamic data of the interaction was fitted well with the one‐site model. The negative values of Gibbs free energy change confirmed the spontaneous nature of the reactions. Besides, the negative values of enthalpy change and entropy change proved that the nature of processes was “enthalpy driven.” The interaction stoichiometry was 2 for AS1411 and Tel21 and 1.5 for Tel45. The binding constants were 1.3(±0.3) × 105, 3.2(±0.4) × 105, and 1.1(±0.3) × 105 M−1, which were at the level of ethidium bromide intercalation binding constant given in the literature. The DNA polymerase stop assay further supported the interaction of CuPc with G‐quadruplex DNA. The experimental results confirm that the CuPc has a potential photosensitizer behaviour for photodynamic therapy.

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Section: Uv-vis Spectroscopymentioning

confidence: 99%

Thermodynamic and structural investigation of the interaction of quaternized 2,3‐octakis‐[(2‐mercaptopyridine)phthalocyaninato] copper (II) sulfate (CuPc) with parallel and hybrid type G‐quadruplex

Şahin,

Bağda,

Göktuğ Temiz

et al. 2023

J of Molecular Recognition

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“…4–9 In the field of organic photosensitizers, metallophthalocyanines (MPcs) play an important role due to their excellent photo- and electro-chemical stability and exclusive light-harvesting capability in the red/NIR spectral regions. 10–13…”

Section: Introductionmentioning

confidence: 99%

“…[4][5][6][7][8][9] In the eld of organic photosensitizers, metallophthalocyanines (MPcs) play an important role due to their excellent photo-and electro-chemical stability and exclusive light-harvesting capability in the red/NIR spectral regions. [10][11][12][13] The main disadvantages of MPcs in PDT are the lack of solubility and selectivity; therefore, the combination of magnetic iron oxide nanoparticles with a photosensitizer is a new and promising approach in PDT. Fe 3 O 4 nanoparticles have been successfully applied in tumor therapy by inducing hyperthermia and oxidative stress that lead to tumor cell damage.…”

Section: Introductionmentioning

confidence: 99%

Photophysics of tetracarboxy-zinc phthalocyanine photosensitizers

et al. 2022

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“…Coumarins-fused pyridine hybrids are the most important type of pharmaceutical intermediates, and are defined in the literature as potential anti-osteoporotic agents [20] . They have a high bio-compatibility due to the nitrogen atom that can form hydrogen bonds with biological molecules [21] .…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, chemical reactivity, kinetic and thermodynamic studies of new ligand derived from 4-hydroxycoumarin: Interaction with SARS-CoV-2

Ait‐Ramdane‐Terbouche

Abdeldjebar

Terbouche

et al. 2020

Journal of Molecular Structure

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Highlights New coumarin derivative (4-[( pyridin -3- ylmethyl ) amino ]−2 H -chromen-2-one) (L TA ) was synthesized and characterized by spectroscopic techniques. The ligand was characterized by single-crystal X-ray diffraction method and optimized by DFT method. The chemical reactivity, kinetic and thermodynamic parameters of L TA were calculated. The interaction of L TA with SARS-CoV-2/Main protease (Mpro) was studied. The docking simulation showed active L TA molecule with the ability to inhibit SARS-CoV-2.

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In vitro photodynamic activities of zinc(II) phthalocyanines substituted with pyridine moieties

Cited by 21 publications

References 6 publications

Thermodynamic and structural investigation of the interaction of quaternized 2,3‐octakis‐[(2‐mercaptopyridine)phthalocyaninato] copper (II) sulfate (CuPc) with parallel and hybrid type G‐quadruplex

Thermodynamic and structural investigation of the interaction of quaternized 2,3‐octakis‐[(2‐mercaptopyridine)phthalocyaninato] copper (II) sulfate (CuPc) with parallel and hybrid type G‐quadruplex

Photophysics of tetracarboxy-zinc phthalocyanine photosensitizers

Crystal structure, chemical reactivity, kinetic and thermodynamic studies of new ligand derived from 4-hydroxycoumarin: Interaction with SARS-CoV-2

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