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

https://doi.org/10.32362/2410-6593-2017-12-4-65-74

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Abstract

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.

About the Authors

E. D. Shuina
Moscow Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation
Moscow 119571, Russia


I. S. Shchelik
Moscow Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation
Moscow 119571, Russia


Yu. L. Sebyakin
Moscow Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation
Moscow 119571, Russia


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For citation:


Shuina E.D., Shchelik I.S., Sebyakin Yu.L. SYNTHESIS AND PROPERTIES OF NEOGLYCOLIPIDS BASED ON 2-AMINO-2-HYDROXYMETHYLPROPANE-1,3-DIOL. Fine Chemical Technologies. 2017;12(4):65-74. (In Russ.) https://doi.org/10.32362/2410-6593-2017-12-4-65-74

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ISSN 2410-6593 (Print)
ISSN 2686-7575 (Online)