Delivery nanosystems based on sterically hindered phenol derivatives containing a quaternary ammonium moiety: Synthesis, cholinesterase inhibition and antioxidant activity

Pashirova, Tatiana N.; Burilova, Evgenia A.; Тагашева, Р. Г.; Zueva, Irina V.; Гибадуллина, Э. М.; Nizameev, Irek R.; Sudakov, Igor A.; Vyshtakalyuk, A. B.; Voloshina, A. D.; Kadirov, Marsil K.; Петров, К. А.; Бурилов, А. Р.; Бухаров, С. В.; Zakharova, L. Ya.

doi:10.1016/j.cbi.2019.108753

Cited by 18 publications

(13 citation statements)

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“…Antioxidants possess great potential as drugs suitable for the treatment of various diseases related to oxidative stress. In particular, the use of compounds containing phenol structural moiety in the treatment of Alzheimer's disease [32][33][34][35][36], Parkinson´s disease [37][38][39], Huntington´s disease [40,41], and cancer [42][43][44][45] have been extensively studied in the last two years. Their structural diversity provides many possibilities for the design and synthesis of new, highly effective agents.…”

Section: Introductionmentioning

confidence: 99%

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

et al. 2020

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A series of 1,3,5-triazine analogues, incorporating aminobenzene sulfonamide, aminoalcohol/phenol, piperazine, chalcone, or stilbene structural motifs, were evaluated as potential antioxidants. The compounds were prepared by using step-by-step nucleophilic substitution of chlorine atoms in starting 2,4,6-trichloro-1,3,5-triazine. Reactions were catalyzed by Cu(I)-supported on a weakly acidic resin. The radical scavenging activity was determined in terms of %inhibition activity and EC50, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest concentration 1 × 10−4 M, the %inhibition activity values at 0 min were comparable with both standards at least for 10 compounds. After 60 min, compounds 5, 6, 13, and 25 showed nearly twice %inhibition (73.44–87.09%) in comparison with the standards (Trolox = 41.49%; ASA = 31.07%). Values of EC50 at 60 min (17.16–27.78 μM) were 5 times lower for compounds 5, 6, 13, and 25 than EC50 of both standards (trolox = 178.33 μM; ASA = 147.47 μM). Values of EC50 correlated with %inhibition activity. Based on these results, the presented 1,3,5-triazine analogues have a high potential in the treatment of illnesses caused or related to oxidative stress.

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Section: Introductionmentioning

confidence: 99%

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

et al. 2020

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“…Research activity of our group focuses on self-assembling amphiphilic systems, with their design, aggregation ability and functionality as drug delivery systems emphasized [2,37,38]. Recently, much attention has been paid to non-covalent modification of liposomes with surfactants [37][38][39][40], with cationic liposomes attracting special interest [41][42][43][44][45][46][47]. Main types of lipid-and silicon-containing nanoparticles, comprising many kinds of nanocarriers that can be used to achieve the best medical performance.…”

Section: Lipid Nanocarriers Modified With Amphiphilic Moleculesmentioning

confidence: 99%

“…Research activity of our group focuses on self-assembling amphiphilic systems, with their design, aggregation ability and functionality as drug delivery systems emphasized [2,37,38]. Recently, much attention has been paid to non-covalent modification of liposomes with surfactants [37][38][39][40], with cationic liposomes attracting special interest [41][42][43][44][45][46][47]. In [39,40] lipid nanoformulations based on L-α-phosphatidylcholine (PC), cholesterol (CHO) and hybrid amphiphilic ligands-quaternary ammonium salts with a sterically hindered phenolic (SHP) moiety with benzyl (SHP-2-Bn) and alkyl tails (SHP-2-R, where R=C n H 2n+1 , n = 8, 10, 12, 16) were obtained and characterized.…”

Section: Lipid Nanocarriers Modified With Amphiphilic Moleculesmentioning

confidence: 99%

“…Recently, much attention has been paid to non-covalent modification of liposomes with surfactants [37][38][39][40], with cationic liposomes attracting special interest [41][42][43][44][45][46][47]. In [39,40] lipid nanoformulations based on L-α-phosphatidylcholine (PC), cholesterol (CHO) and hybrid amphiphilic ligands-quaternary ammonium salts with a sterically hindered phenolic (SHP) moiety with benzyl (SHP-2-Bn) and alkyl tails (SHP-2-R, where R=C n H 2n+1 , n = 8, 10, 12, 16) were obtained and characterized. Cationic liposomes based on PC with a diameter of 100 nm, modified with benzyl derivatives of SHP, exhibit more pronounced antioxidant activity than individual SHP-n-Bn.…”

Section: Lipid Nanocarriers Modified With Amphiphilic Moleculesmentioning

confidence: 99%

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Nanocarriers for Biomedicine: From Lipid Formulations to Inorganic and Hybrid Nanoparticles

Kashapov

Ibragimova

Pavlov

et al. 2021

IJMS

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Encapsulation of cargoes in nanocontainers is widely used in different fields to solve the problems of their solubility, homogeneity, stability, protection from unwanted chemical and biological destructive effects, and functional activity improvement. This approach is of special importance in biomedicine, since this makes it possible to reduce the limitations of drug delivery related to the toxicity and side effects of therapeutics, their low bioavailability and biocompatibility. This review highlights current progress in the use of lipid systems to deliver active substances to the human body. Various lipid compositions modified with amphiphilic open-chain and macrocyclic compounds, peptide molecules and alternative target ligands are discussed. Liposome modification also evolves by creating new hybrid structures consisting of organic and inorganic parts. Such nanohybrid platforms include cerasomes, which are considered as alternative nanocarriers allowing to reduce inherent limitations of lipid nanoparticles. Compositions based on mesoporous silica are beginning to acquire no less relevance due to their unique features, such as advanced porous properties, well-proven drug delivery efficiency and their versatility for creating highly efficient nanomaterials. The types of silica nanoparticles, their efficacy in biomedical applications and hybrid inorganic-polymer platforms are the subject of discussion in this review, with current challenges emphasized.

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“…It was shown that the highest value of encapsulation efficiency, equal to 75%, is achieved in the case of surface modification with an octadecyl derivative. New sterically hindered phenol containing a quaternary ammonium moiety (SHP-n-Q) was also used for incorporation into liposomes [ 223 ]. Mixed liposomes based on L-α-phosphatidylcholine and SHP-n-Q showed long-term stability (1 year) and prolonged release of rhodamine B.…”

Section: Self-assembled Amphiphilic Systems As Smart Drug Nanocarrmentioning

confidence: 99%

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

Kashapov

Gaynanova

Gabdrakhmanov

et al. 2020

IJMS

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This review focuses on synthetic and natural amphiphilic systems prepared from straight-chain and macrocyclic compounds capable of self-assembly with the formation of nanoscale aggregates of different morphology and their application as drug carriers. Since numerous biological species (lipid membrane, bacterial cell wall, mucous membrane, corneal epithelium, biopolymers, e.g., proteins, nucleic acids) bear negatively charged fragments, much attention is paid to cationic carriers providing high affinity for encapsulated drugs to targeted cells. First part of the review is devoted to self-assembling and functional properties of surfactant systems, with special attention focusing on cationic amphiphiles, including those bearing natural or cleavable fragments. Further, lipid formulations, especially liposomes, are discussed in terms of their fabrication and application for intracellular drug delivery. This section highlights several features of these carriers, including noncovalent modification of lipid formulations by cationic surfactants, pH-responsive properties, endosomal escape, etc. Third part of the review deals with nanocarriers based on macrocyclic compounds, with such important characteristics as mucoadhesive properties emphasized. In this section, different combinations of cyclodextrin platform conjugated with polymers is considered as drug delivery systems with synergetic effect that improves solubility, targeting and biocompatibility of formulations.

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Delivery nanosystems based on sterically hindered phenol derivatives containing a quaternary ammonium moiety: Synthesis, cholinesterase inhibition and antioxidant activity

Cited by 18 publications

References 50 publications

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

Nanocarriers for Biomedicine: From Lipid Formulations to Inorganic and Hybrid Nanoparticles

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

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