Decline of Prooxidant Activity of Butyl and Phenyl Derivatives of Tin in the Presence of meso-Tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin

Kolyada, M. N.; Osipova, Victoriya P.; Берберова, Н. Т.; Pimenov, Yuri T.; Милаева, Е. Р.

doi:10.6060/mhc160542o

Cited by 4 publications

(1 citation statement)

References 20 publications

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“…It was found that the nature of the metal centre and peripheral substituents is a very important factor for dictating porphyrin antioxidant activity and efficiency [ 42 , 43 ]. For example, cationic Mn(III) and Fe(III) N-substituted pyridylporphyrins [ 44 , 45 , 46 ] and tetrasubstituted porphyrins functionalised with antioxidant di- tert -butylphenol groups were shown to be efficient antioxidants and biomimetics of superoxide dismutase [ 42 , 44 , 47 ].…”

Section: Introductionmentioning

confidence: 99%

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Теплоногова

Volostnykh

Yapryntsev

et al. 2022

IJMS

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In this study, organo-inorganic nanohybrids LHGd-MTSPP with enzyme-like activity were prepared by in situ intercalation of anionic 5,10,15,20-tetrakis-(4-sulfonatophenyl)porphyrin and its complexes with Zn(II) and Pd(II) (MTSPP, M = 2H, Zn(II) and Pd(II)) into gadolinium layered hydroxide (LHGd). The combination of powder XRD, CHNS analysis, FT-IR, EDX, and TG confirmed the layered structure of the reaction products. The basal interplanar distances in LHGd-MTSPP samples were 22.3–22.6 Å, corresponding to the size of an intercalated tetrapyrrole molecule. According to SEM data, LHGd-MTSPP hybrids consisted of individual lamellar nanoparticles 20–50 nm in thickness. The enzyme-like activity of individual constituents, LHGd-Cl and sulfoporphyrins TSPP, ZnTSPP and PdTSPP, and hybrid LHGd-MTSPP materials, was studied by chemiluminescence analysis using the ABAP/luminol system in phosphate buffer solution. All the individual porphyrins exhibited dose-dependent antioxidant properties with respect to alkylperoxyl radicals at pH 7.4. The intercalation of free base TSPP porphyrin into the LHGd preserved the radical scavenging properties of the product. Conversely, in LHGd-MTSPP samples containing Zn(II) and Pd(II) complexes, the antioxidant properties of the porphyrins changed to dose-dependent prooxidant activity. Thus, an efficient approach to the design and synthesis of advanced LHGd-MTSPP materials with switchable enzyme-like activity was developed.

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Section: Introductionmentioning

confidence: 99%

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Теплоногова

Volostnykh

Yapryntsev

et al. 2022

IJMS

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Porphyrins with Phenolic Fragments at the Periphery of the Macrocycle as Perspective Antioxidants, Cytoprotectors and Heavy Metal Scavengers

Kolyada

Осипова

Берберова

et al. 2021

Chem Heterocycl Comp

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Novel selective anticancer agents based on Sn and Au complexes. Mini-review

Милаева

Shpakovsky

Gracheva

et al. 2020

Pure and Applied Chemistry

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Cancer is one of the most common causes of death in modern medicine. Molecular design of novel substances with pharmacological activity is one of the goals of medicinal inorganic chemistry. Platinum complexes are widely used in the treatment of cancer, despite high efficacy their use is limited by side effects, as well as primary or acquired resistance. In this regard, the search for novel metal-containing antitumor compounds is underway. Organotins and gold compounds are promising pharmacological agents with anti-cancer properties. The introduction of protective antioxidant fragments into inorganic compounds molecules is a way to reduce the side effects of anti-cancer drugs on healthy cells. 2,6-dialkylphenols belonging to vitamin E (α-tocopherol) mimetics are widely used as antioxidants and stabilizers. The properties of Ph3SnCl (Sn-I), Ph3PAuCl (Au-I) and complexes Ph3SnSR (Sn-II) and Ph3PAuSR (Au-II) based on 2,6-di-tert-butyl-4-mercaptophenol (RSH) as radical scavengers and reducing agents were studied in model reactions. For Sn-II and Au-II the comparative study of cytotoxic action was made and the IC50 values on different cancer cell lines were found to be depended on the nature of metal. In general, Sn(IV) complexes possessed higher cytotoxicity than Au(I) complexes. In order to clarify the mechanism of cytotoxic mode of action the effect of compounds on Fe3+-induced lipid peroxidation, mitochondrial potential and mitochondrial permeability, cell cycle and induction of apoptosis was studied. Organotin compounds can bind tubulin SH-groups and inhibit its polymerization by a dose-dependent mechanism, whereas gold compounds inhibit Thioredoxin reductase (TrxR). In vivo experiments on acute toxicity of Sn-II and Au-II proved their moderate toxic action that opens prospects for the further study as antitumor agents.

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Decline of Prooxidant Activity of Butyl and Phenyl Derivatives of Tin in the Presence of meso-Tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin

Cited by 4 publications

References 20 publications

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Porphyrins with Phenolic Fragments at the Periphery of the Macrocycle as Perspective Antioxidants, Cytoprotectors and Heavy Metal Scavengers

Novel selective anticancer agents based on Sn and Au complexes. Mini-review

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