СИНТЕЗ И СВОЙСТВА НЕОГЛИКОЛИПИДОВ НА ОСНОВЕ 2-АМИНО-2-ГИДРОКСИМЕТИЛПРОПАН-1,3-ДИОЛА

The use of TRIS derivatives as the kernels of branching fragments is a modern method of preparing carbohydrate-containing dendrimer-like amphiphiles. A scheme of the synthesis of derivatives of trivalent neoglycolipids with terminal residues of D-mannose and a branching component based on 2-amino-2-hydroxymethylpropene-1,3-diol (TRIS) differing in the degree of saturation of the hydrocarbon chains is developed. The preparation of the hydrophilic part of the target molecules was carried out with the use of the reaction of 1,3-dipolar cycloaddition followed by conjugation with the hydrophobic component according to the carbodiimide method with the addition of HOBt as a catalyst. Approaches to the formation of target designs - liposomes based on phosphatidylcholine and synthesized neoglycolipids - and their physical and chemical properties, such as the size of particles and stability are investigated. The activity of the obtained compounds in the composition of liposomes loaded with the antibiotic meropenem with respect to Escherichia coli strain is carried out. An opportunity of changing the profile of the action of a liposome sample containing neoglycolipids by choosing various methods of its preparation that is promising for further research in this direction is revealed.Использование в качестве ядер разветвляющих фрагментов производных TRIS является современным методом получения углеводсодержащих дендримероподобных амфифилов. Разработана схема синтеза получения производных трехвалентных неогликолипидов с терминальными остатками D-маннозы и разветвляющей компонентой на основе 2-амино-2-гидроксиметилпропан-1,3-диола (TRIS), различающиеся степенью насыщенности углеводородных цепей. Получение гидрофильной части целевых молекул проводили по реакции 1,3-диполярного циклоприсоединения, с дальнейшей конъюгацией с гидрофобной компонентой карбодиимидным способом с добавкой HOBt в качестве катализатора. В работе исследованы подходы к формированию целевых конструкций - липосом на основе фосфатидилхолина и синтезированных неогликолипидов и их физико-химические свойства, такие как размер частиц и стабильность. Изучена активность полученных соединений в составе липосом, загруженных антибиотиком меропенемом, в отношении штамма бактерий Escherichia coli. Выявлена возможность изменять профиль действия образца липосом, содержащих неогликолипиды, выбором различных методов его приготовления, что перспективно для дальнейших исследований в этом направлении

Тетравалентный неогликоконъюгат на основе d-галактозы для целей медицины

Previously, the scheme of the preparation of a tetravalent neoglycoconjugate with the terminal residues of D-galactose and with a branching component based on D-galactose was carried out in our laboratory. It includes the synthesis of hydrophilic and hydrophobic components, the synthesis of the branching scaffold and its conjugation with a hydrophilic component. This article describes the optimization of the synthesis of 1-O-azidoethyl-β-D-galactopyronaside using the change of different parameters such as temperature, solvent and reaction time. The structure of obtained glycoconjugates has potential to be capable to anti-adhesion and target delivery to certain cell group.Проведена оптимизация ранее разработанной схемы синтеза тетравалентного неогликоконъюгата с терминальными остатками D-галактозы и разветвляющей компонентой на основе D-галактозы. Структура полученных гликоконъюгатов обеспечивает им потенциальную возможность проявлять свойства антиадгезии и специфически связываться с рецепторами на определенных группах клеток

SYNTHESIS AND PROPERTIES OF NEOGLYCOLIPIDS BASED ON 2-AMINO-2-HYDROXYMETHYLPROPANE-1,3-DIOL

The use of TRIS derivatives as the kernels of branching fragments is a modern method of preparing carbohydrate-containing dendrimer-like amphiphiles. A scheme of the synthesis of derivatives of trivalent neoglycolipids with terminal residues of D-mannose and a branching component based on 2-amino-2-hydroxymethylpropene-1,3-diol (TRIS) differing in the degree of saturation of the hydrocarbon chains is developed. The preparation of the hydrophilic part of the target molecules was carried out with the use of the reaction of 1,3-dipolar cycloaddition followed by conjugation with the hydrophobic component according to the carbodiimide method with the addition of HOBt as a catalyst. Approaches to the formation of target designs - liposomes based on phosphatidylcholine and synthesized neoglycolipids - and their physical and chemical properties, such as the size of particles and stability are investigated. The activity of the obtained compounds in the composition of liposomes loaded with the antibiotic meropenem with respect to Escherichia coli strain is carried out. An opportunity of changing the profile of the action of a liposome sample containing neoglycolipids by choosing various methods of its preparation that is promising for further research in this direction is revealed

Tetravalent neoglycoсonjugate based on the d-galactose for medicine purposes

Previously, the scheme of the preparation of a tetravalent neoglycoconjugate with the terminal residues of D-galactose and with a branching component based on D-galactose was carried out in our laboratory. It includes the synthesis of hydrophilic and hydrophobic components, the synthesis of the branching scaffold and its conjugation with a hydrophilic component. This article describes the optimization of the synthesis of 1-O-azidoethyl-β-D-galactopyronaside using the change of different parameters such as temperature, solvent and reaction time. The structure of obtained glycoconjugates has potential to be capable to anti-adhesion and target delivery to certain cell group