The first peptide derivatives of dioxybiphenyl-bridged spiro cyclotriphosphazenes: In vitro cytotoxicity activities and DNA damage studies

Koran, Kenan; Çalışkan, Eray; Öztürk, Dilara Altay; Çapan, İrfan; Tekin, Suat; Sandal, Süleyman; Görgülü, Ahmet Orhan

doi:10.1016/j.bioorg.2022.106338

Cited by 19 publications

(4 citation statements)

References 67 publications

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“…Phosphazenes are a class of organic-inorganic compounds with chemical lability, which provides them with a wide range of valuable properties and applications. Phosphazenes are non-toxic and can even be used in pharmaceuticals [24][25][26]. Porous polymers based on phosphazenes are used in environmentally friendly sorption processes [27] and industrial catalysis [28], and some cyclophosphazenes even have an anti-corrosion effect towards metals, which is important in the manufacture of metal-containing composites [29].…”

Section: Introductionmentioning

confidence: 99%

Non-Flammable Epoxy Composition Based on Epoxy Resin DER-331 and 4-(β-Carboxyethenyl)phenoxy-phenoxycyclotriphosphazenes with Increased Adhesion to Metals

Konstantinova,

Yudaev,

Shapagin

et al. 2024

Sci

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Functional cyclophosphazenes have proven to be effective modifiers of polymer materials, significantly improving their performance properties, such as adhesive characteristics, mechanical strength, thermal stability, fire resistance, etc. In this study, 4-(β-carboxyethenyl)phenoxy-phenoxycyclotriphosphazenes (CPPP) were obtained by the condensation of 4-formylphenoxy-phenoxycyclotriphosphazene with malonic acid. Its structure was studied using 31P, 1H, and 13C NMR spectroscopy and MALDI-TOF mass spectrometry, and the thermal properties were determined by DSC and TGA methods. Molecular modeling using the MM2 method showed that CPPPs are nanosized with diameters of spheres described around the molecules in the range of 1.34–1.93 nm, which allows them to be classified as nanosized structures. The epoxy resin DER-331 was cured with CPPP, and the conversion of epoxy groups was assessed using IR spectroscopy. Using optical interferometry, it was shown that CPPPs are well compatible with epoxy resin in the temperature range from 80 to 130 °C. It was established that the cured epoxy composition was fire resistant, as it successfully passed the UL-94 vertical combustion test due to the formation of porous coke during the combustion process and also had high heat resistance and thermal stability (decomposition onset temperature about 300 °C, glass transition temperature 230 °C). The composition has low water absorption, high resistance to fresh and salt water, fire resistance, and adhesive strength to steel and aluminum (11 ± 0.2 MPa), which makes it promising for use as an adhesive composition for gluing parts in the shipbuilding and automotive industries, the aviation industry, and radio electronics.

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Section: Introductionmentioning

confidence: 99%

Non-Flammable Epoxy Composition Based on Epoxy Resin DER-331 and 4-(β-Carboxyethenyl)phenoxy-phenoxycyclotriphosphazenes with Increased Adhesion to Metals

Konstantinova,

Yudaev,

Shapagin

et al. 2024

Sci

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“…The chemical and physical properties of cyclotriphosphazenes change with the nature of substituted side groups. Therefore, it is possible to design materials with special properties such as biological active molecules [15][16][17][18][19], sensor molecules [20,21], liquid crystal molecules [22,23]. Also, N-heterocyclic-based cyclophosphazene ligands supply a rich coordination chemistry via multiple N-donor atoms [24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Ag(I) and Hg(II) Coordination Polymers Decorated from Fully Benzimidazole Substituted Cyclotriphosphazene Ligand and Adsorption Behaviour Against Methylene Blue

Pendar,

Duyar,

Zorlu

et al. 2024

J Inorg Organomet Polym

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Herein, we reported new two coordination polymers, {[Ag(L)](CH 3 PhSO 3 )](CH 3 CN) 4 } n (cp-1) and {[Hg(L)](Cl 2 )] (CH 3 CN) 2 } n (cp-2), were synthesized from hexapodal benzimidazole substituted cyclotriphosphazene, (L). L was characterised by 1 H NMR, 31 P NMR and mass analysis. Structure of each isolated compounds were determined by single crystal X-ray crystallography. In cp-1, L has a κ 3 N coordination mode by connecting three Ag(I) ions to constitute a 2D coordination framework whereas the ligand in cp-2 displays κ 2 N coordination mode via linking four Hg(II) ions together to create a 1D coordination polymer. Topologically, cp-1 has a 3-connected uninodal net having the point symbol {4.8 2 }. Dye adsorption studies of coordination polymers was performed out using UV-Vis. absorption spectroscopy. Adsorption experiments show that cp-1 and cp-2 removes the cationic methylene blue (MB) from water but shows no adsorption behaviour toward the anionic methyl orange (MO) and tartrazine (E102).

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“…Cyclophosphazenes, due to their biocompatibility, act as precursors for the synthesis of biologically active compounds used in pharmaceuticals. Di and tetra dipeptide substituted spiro cyclotriphosphazenes have a cytotoxic effect on cancer cells of the human breast, ovaries, prostate, and colon [ 33 ]. Chalkone-substituted cyclotriphosphazenes reduce the viability of human ovarian and prostate cancer cells by 70–90% [ 34 , 35 ].…”

Section: Introductionmentioning

confidence: 99%

Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure

Yudaev,

Konstantinova,

Volkov

et al. 2023

Molecules

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Condensation of hexakis-2-(formylphenoxy)cyclotriphosphazene with malonic acid yielded hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene (2-CEPP), whose structure was confirmed by 31P, 1H, 13C NMR spectroscopy and MALDI-TOF mass spectrometry. A quantum-chemical calculation for the 2-CEPP molecule using the ab initio methods in the 6-311G** basis set and the DFT-PBE0/6-311g** method was performed with geometry optimization of all parameters by the standard gradient method. The acid strength of 2-CEPP was theoretically estimated. Using the small-angle X-ray scattering method, it was found that 2-CEPP is an amorphous substance, which, when heated, can transform into a crystalline state. However, when heated at 370 °C, 2-CEPP undergoes decarboxylation and polymerization to form an insoluble heat-resistant product. The occurrence of decarboxylation and polymerization reactions in the formed styrene fragments was confirmed by thermal (differential-scanning calorimetry) and spectral (solid-state 13C NMR spectroscopy) analysis.

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The first peptide derivatives of dioxybiphenyl-bridged spiro cyclotriphosphazenes: In vitro cytotoxicity activities and DNA damage studies

Cited by 19 publications

References 67 publications

Non-Flammable Epoxy Composition Based on Epoxy Resin DER-331 and 4-(β-Carboxyethenyl)phenoxy-phenoxycyclotriphosphazenes with Increased Adhesion to Metals

Non-Flammable Epoxy Composition Based on Epoxy Resin DER-331 and 4-(β-Carboxyethenyl)phenoxy-phenoxycyclotriphosphazenes with Increased Adhesion to Metals

Ag(I) and Hg(II) Coordination Polymers Decorated from Fully Benzimidazole Substituted Cyclotriphosphazene Ligand and Adsorption Behaviour Against Methylene Blue

Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure

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