Synthesis of conjugates of 5,15-disubstituted aminoporphyrins and terpyridine derivatives with potential chelating properties

Vyal’ba, Fedor Yu.; Ivantsova, Anastasia V.; Zhdanova, Kseniya A.; Usachev, Maxim N.; Gradova, Margaret A.; Брагина, Н. А.

doi:10.1016/j.mencom.2022.09.036

Cited by 3 publications

(1 citation statement)

References 34 publications

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“…In order to improve the yield of this reaction, the synthesis of conjugate 14 acylation by Schotten-Baumann was used. Thus, compound 10 was treated with chlorohydride of 4-([2,2′:6′,2′-terpyridine]-4′-yl) benzoic acid [ 47 ] in the presence of Et 3 N. The yield of the acylation reaction was almost quantitative (96%). The identity and chemical structure of the obtained conjugates 12–15 were confirmed by thin layer chromatography, EAS, 1 H- and 13 C-NMR spectroscopy, 1 H- 1 H COSY, mass spectrometry and HPLC-HRMS ( SI, Figures S36–S48 ).…”

Section: Resultsmentioning

confidence: 99%

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

et al. 2023

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This paper reports on the design and synthesis of new multifunctional porphyrin-based therapeutic agents for potential therapeutic and diagnostic applications. Zinc complexes of A3B-type meso-arylporphyrins containing OH- and COOH- groups were modified with chelating ligands based on 4′-(4-methylphenyl)-2,2′:6′,2″-terpyridine derivatives in high yields. Novel complexes with Gd(III), Fe(III) were obtained for these conjugates. Aggregation behaviour in solutions of different solubilisers was studied to inform the selection of the optimal solubilising platform for the porphyrins obtained; their photophysical and photochemical properties were also characterised. Micellar Pluronic F127 formulation was found to be the most effective solubiliser for stabilising the fluorescence-active monomolecular form of the photosensitisers (PS). In vitro cytotoxicity of the compounds was studied on the HEP-2 cell line with and without irradiation for 1.5 and 24 h. As a result, the IC50 of compounds 12 and 14 at an irradiation dose of 8.073 J/cm2 was shown to be 1.87 ± 0.333 and 1.4 ± 0.152 μM, respectively; without irradiation, the compound had no toxic effect within the studied concentration range (1.5 h). A test for the inhibition of metabolic cooperation or promoter activity was also performed for the abovementioned compounds, showing the efficacy and safety of the conjugates obtained. Preliminary data have indicated the high potential of the new type of PS to be promising molecular theranostic agents.

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Section: Resultsmentioning

confidence: 99%

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

et al. 2023

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Structure and properties of the metal-containing monomer based on nickel acrylate and 4’-phenyl-2,2’:6’,2’’-terpyridine for self-healing polymers

Sorin,

Baimuratova,

Tkachev

et al. 2024

Mendeleev Communications

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Potential agents for combined photodynamic and chemotherapy in oncology based on Pt(II) complexes and pyridine-containing natural chlorins

Grin¹,

Ostroverkhov²,

Suvorov³

et al. 2023

J. Porphyrins Phthalocyanines

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Combined therapy is currently a popular method for increasing the efficiency of antitumor treatment. It involves the use of two different tumor treatment methods, namely, chemotherapy and PDT. Combining a cytotoxic agent and a photosensitizer in a single molecule results in a synergistic antitumor effect that overcomes the multiple drug resistance and reduces the therapeutic drug doses. In this work, pyridine-containing natural chlorins were obtained by introducing a pyridine group into 131-[Formula: see text]-(4-aminobutyl)amide of chlorin [Formula: see text] and its bacteriochlorin analogue, [Formula: see text]-propyloxime-[Formula: see text]-propoxybacteriopurinimide as well as [Formula: see text]-aminobacteriopurinimide methyl ester. Moreover, a terpyridine residue was introduced as an external chelating moiety into [Formula: see text]-hydroxypurpurinimide and [Formula: see text]-aminobacteriopurinimide, and platinum complexes of all the above photosensitizers were obtained. The interactions of the latter with DNA were simulated and the lead compound, the platinum complex of pyridine derivative 131-[Formula: see text]-(4-aminobutyl)amide chlorin [Formula: see text], which may become a potential agent for combined photodynamic and chemotherapy in oncology, was selected. The ability of the compounds obtained to manifest photodynamic and chemocytotoxic effects on tumor cells of various genesis was shown.

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Synthesis of conjugates of 5,15-disubstituted aminoporphyrins and terpyridine derivatives with potential chelating properties

Cited by 3 publications

References 34 publications

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

Structure and properties of the metal-containing monomer based on nickel acrylate and 4’-phenyl-2,2’:6’,2’’-terpyridine for self-healing polymers

Potential agents for combined photodynamic and chemotherapy in oncology based on Pt(II) complexes and pyridine-containing natural chlorins

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