Binding and photodynamic action of the cationic zinc phthalocyanines with different types of DNA toward understanding of their cancer therapy activity

McRae, Ewan K.S.; Nevonen, Dustin E.; McKenna, Sean Andrew; Nemykin, Victor N.

doi:10.1016/j.jinorgbio.2019.110793

Cited by 24 publications

(14 citation statements)

References 65 publications

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“…[55,56] Several studies also have shown that positive electric charge is able to promote the PDT effects in cancer therapy. [57][58][59] However, it was also found that the photodynamic effect may decrease gradually with the increase in the number of positive charges . [60] Thus, the amount of positive electric charges of the photosensitizer should be carefully optimized.…”

Section: Singlet Oxygen Generation Measurementsmentioning

confidence: 99%

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

et al. 2020

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Boron‐dipyrromethene derivatives, including cationic and iodinated analogs, were obtained and subjected to physicochemical and in vitro photodynamic activity studies. Iodinated derivatives revealed a substantial heavy atom effect manifested by a bathochromic shift of the absorption band by about 30 nm and fluorescence intensity reduced by about 30–35 times, compared to that obtained for non‐iodinated ones. In consequence, singlet oxygen generation significantly increased with ΦΔ values in the range 0.69–0.97. The in vitro photodynamic activity was evaluated on Gram‐positive Staphylococcus aureus, Gram‐negative Escherichia coli, and on human androgen‐sensitive prostate adenocarcinoma cells (LNCaP). The novel cationic, iodinated BODIPY, demonstrated the highest activity toward all studied cells. An excellent cytotoxic effect was found against LNCaP cells with an IC50 value of 19.3 nM, whereas the viability of S. aureus was reduced by >5.6 log10 at 0.25 μM concentration and by >5.3 log10 in the case of E. coli at 5 μM. Thus, this analog seems to be a very promising candidate for the application in both anticancer and antimicrobial photodynamic therapy.

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Section: Singlet Oxygen Generation Measurementsmentioning

confidence: 99%

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

et al. 2020

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“…Fluorescent compounds; In today's technology has important uses such as disease diagnosis and treatment [25]. Sensor materials such as bio marking [25], environmental indicator [26], enzyme substrate [27], cell-organelle marking [28], radiation emitting diodes [29], chemistry [30], molecules biology [30] and physics [31] have become an integral part of science. Fluorescence excitation, absorption and emission spectra of zinc phthalocyanine compound, which shows fluorescence from these compounds, were examined in THF solvent.…”

Section: Fluorescent Spectramentioning

confidence: 99%

Design of novel substituted phthalocyanines; synthesis and fluorescence, DFT, photovoltaic properties

Ağırtaş¹,

Solğun²,

Yıldıko³

et al. 2020

Turk J Chem

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The 4-(2-(3,4-dimethoxyphenoxy) phenoxy) phthalonitrile was synthesized as the starting material of new syntheses. Zinc, copper, and cobalt phthalocyanines were achieved by reaction of starting compound with Zn(CH3COO)2, CuCl2 and CoCl2 metal salts. Basic spectroscopic methods such as nuclear magnetic resonance electronic 2 absorption, mass and infrared were used in the structure characterization of the compounds. Absorption, excitation and emission measurements of fluorescence zinc phthalocyanine compound were also investigated in THF. Then, structural, energy and electronic properties for synthesized metallophthalocyanines were determined by quantum chemical calculations including DFT method. The band gap of HOMO and LUMO was determined to be chemically active. Global reactivity (I, A, η, s, μ, χ, ω) and non-linear properties were studied. In addition, molecular electrostatic potential (MEP) maps were drawn to identify potential reactive regions of metallo phthalocyanine (M-Pc) compounds. Photovoltaic performances of phthalocyanine compounds for dye sensitive solar cells were investigated. Solar conversion efficiency of DSSC based on copper, zinc and cobalt phthalocyanine compounds was 1.69%, 1.35% and 1.54%, respectively. Compounds have good solubility and show nonlinear optical properties. Zinc phthalocyanine gave fluorescence emission.

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“…Besides, it is used in many elds such as catalyst [3], sensor [4,5], liquid crystal [6], optical data storage [7,8], solar cells [9]. Photodynamic therapy, which is one of the cancer treatment methods, is being researched as the subject of intensive research [10][11][12]. The synthesis of phthalocyanine compounds capable of producing appropriate singlet oxygen excites researchers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

Solğun

Yıldıko

Ağırtaş

2021

Polycyclic Aromatic Compounds

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4- (2-(benzo[d] [1, 3] dioxol-5-ylmethoxy) phenoxy) phthalonitrile was rst prepared as a starting material.Then, this new phthalonitrile derivative was reacted with Zn and Co salts to obtain new phthalocyanine complexes. Phthalocyanine complexes were evaluated by uorescence emission, extinction, and absorption measurements. Aggregation studies show the compliance with the lambert-beer law in the concentration range studied for peripheral phthalocyanine compounds. The density functional theory (DFT) calculations of the metallophthalocyanines compounds were performed using B3LYP / 6-31G in Zn-Pc and B3LYP / LanL2DZ in Co-Pc to derive structural optimization, HOMO-LUMO energy parameters, and NLO properties. The calculated values of M-Pcs with different center atoms were obtained close to each other. Molecular electronic surface (MEP) maps of the studied compounds are mapped and discussed. The HOMO-LUMO energy gaps of our compounds studied are around 2.1 eV. The docking studies were performed with the phthalonitrile.

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Binding and photodynamic action of the cationic zinc phthalocyanines with different types of DNA toward understanding of their cancer therapy activity

Cited by 24 publications

References 65 publications

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

Design of novel substituted phthalocyanines; synthesis and fluorescence, DFT, photovoltaic properties

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

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