Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Bilgiçli, Ahmet T.; Bilgiçli, Hayriye Genç; Hepokur, Ceylan; Tüzün, Burak; Günsel, Armağan; Zengin, Mustafa; Yaraşir, M. Nilüfer

doi:10.1002/aoc.6242

Cited by 18 publications

(12 citation statements)

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“…The compound with the higher HOMO energy value has higher activity than the others. [ 68 ] Because it has the ability to donate electrons more easily. [ 69 ] On the other hand, the LUMO energy value of compounds indicates the ability of compounds to accept electrons into vacant orbitals.…”

Section: Resultsmentioning

confidence: 99%

“…Because it has the ability to accept electrons more easily. [ 68 ] By examining these two parameters, they are used to explain the activities of compounds with their ability to donate electrons.Another parameter is the ∆E energy gap, which is equal to the energy value difference between the HOMO and LUMO parameters of the compounds. [ 69 ] The activity of the compound with the lowest numerical value of this parameter is higher than the other compounds.…”

Section: Resultsmentioning

confidence: 99%

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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Quinoline-fused Zn II (ZnPc p /ZnPc np ) and Mg II (MgPc p /MgPc np ) phthalocyanines with four 4-methylquinolin-2-ol (1) at non-peripheral or peripheral positions of the phthalocyanine core have been synthesized via cyclotetramerization of phthalonitrile derivatives (CN p /CN np ) in the presence of zinc (II) and magnesium (II) metal ions in this study. After synthesis and characterization processes, anti-cholinesterase, anti-α-glucosidase, DNA nuclease, antioxidant activities, and in silico calculations of both peripheral and non-peripheral Zn II and Mg II phthalocyanines were investigated. The inhibitory effects of metallated phthalocyanines on acetylcholinesterase, butyrylcholinesterase, and α-glucosidase enzymes were tested by spectrophotometric method. Theoretical methods are used to compare both the chemical and biological activities of the studied phthalonitrile derivatives and metallated phthalocyanine compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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“…The ΔE approach, defined as the HOMO -LUMO energy deficit, is a very important stability index and provides the necessary theoretical models to make explanations about the structure and conformation in molecular systems. In order to have a high inhibition efficiency, the ΔE value should be low [47][48][49]. When the investigated molecules were compared, it was seen that there was a DBAMTT molecule in the smallest HOMO-LUMO gap (8,68921 eV obtained by HF method) as seen in Table 2.…”

Section: Non-protonated Inhibitorsmentioning

confidence: 99%

“…In the theoretical studies, the ESP calculations of the molecules show the regions where the electron density is high in the molecule [49]. For this reason, molecules interact chemically by donating electrons on atoms with higher electron density.…”

Section: Non-protonated Inhibitorsmentioning

confidence: 99%

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Applications of the Effectiveness of Corrosion Inhibitors with Computational Methods and Molecular Dynamics Simulation

Erdoğan¹,

Tüzün²

2022

Corrosion - Fundamentals and Protection Mechanisms

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Many experts working in the field of corrosion work in laboratories experimentally with long-term procedures and high costs by making changes in the structures of new corrosion inhibitors or existing inhibitors. Advances in computational chemistry and computer software in recent years combine corrosion prevention studies with theoretical chemistry, enabling fast, cheap and highly accurate research. Researchers working in this field can now predict the electronic, molecular and adsorption properties of anti-corrosion molecules at the molecular level with density functional theory (DFT) and Molecular Dynamics Simulation. This section includes: introduction, corrosion mechanisms, introduction to corrosion inhibitors, density functional theory (DFT) and corrosion applications, Molecular Dynamics Simulation, DFT and Molecular Dynamics Simulation applications of the effectiveness of the selected corrosion inhibitor and results. The theoretical data obtained by both the DFT approach and the molecular dynamics simulation approach showed that the corrosion inhibition efficiency order against iron corrosion for the studied Schiff bases and derivatives can be presented as: DBAMTT> SAMTT> AMTT. HOMO energy value of DBAMTT has −8,18144, HOMO energy value of SAMTT has −8,09001, and AMTT has −8,01518 in HF/6–31++G** basis set.

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Tumor‐pH‐value responsive non‐peripheral substituted phthalocyanines: Synthesis, investigation of photophysical and photochemical properties

Genc Bilgicli,

Bilgiçli,

Alagöz

et al. 2023

Applied Organom Chemis

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Cancer is one of the diseases with the highest mortality rate worldwide. Although PDT has recently produced encouraging outcomes, there are still many areas that need to be improved. The first of these is the negative consequences faced by patients treated with the PDT method when exposed to sunlight. For this reason, a new PDT method has been developed in recent years, and it is aimed at using photosensitizer molecules that can be active in acidic conditions. Since the pH values of tumor tissues are more acidic than normal tissues, preparing molecules that act effectively in acidic conditions will allow for more effective results in treating cancer with PDT. In this context, within the scope of this study, 3‐(4‐propionylphenoxy)phthalonitrile (1) and its non‐peripheral tetra‐substituted phthalocyanine derivatives [(2), (3), and (4)] were prepared. With these phthalocyanine derivatives, the novel compounds (5), (6), and (7) were synthesized for the first time. The aggregation tendencies of newly synthesized phthalocyanines (5–7) were investigated in solvent media. The effects of pH changes upon UV–Vis and fluorescence spectra were performed. The electronic and emission spectra of synthesized phthalocyanine derivatives are highly sensitive to pH changes. Formation constant (LogK) values of mono‐ and di‐protonated phthalocyanine forms were calculated by the Henderson–Hasselback equation. The mono‐ and di‐protonated species' equilibrium constants (logK1 and logK2) were calculated as ~5.0. This value may be promising for pH‐sensitizing photosensitizers. Also, the photophysical and photochemical properties of synthesized metallophthalocyanine derivatives (2) and (5) were studied at different pH values. The singlet oxygen quantum yield of (2) and (5) was calculated to be 0.78 and 0.81 in DMSO, respectively. When pH = 6.4, that is, tumor‐pH‐values, this value for (5) has increased to 0.92. The newly synthesized phthalocyanines are suitable photosensitizers for PDT applications, especially with high singlet oxygen quantum yield at pH 6.4.

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Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Cited by 18 publications

References 50 publications

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Applications of the Effectiveness of Corrosion Inhibitors with Computational Methods and Molecular Dynamics Simulation

Tumor‐pH‐value responsive non‐peripheral substituted phthalocyanines: Synthesis, investigation of photophysical and photochemical properties

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Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Cited by 18 publications

References 50 publications

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Applications of the Effectiveness of Corrosion Inhibitors with Computational Methods and Molecular Dynamics Simulation

Tumor‐pH‐value responsive non‐peripheral substituted phthalocyanines: Synthesis, investigation of photophysical and photochemical properties

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Product

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies