Fine Chemical Technologies

Advanced search


Full Text:


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


1. Jebali A. Nano-carbohydrates: Synthesis and application in genetics, biotechnology, and medicine // Advances in Colloid and Interface Science. 2016. № 240. Р. 1–14.

2. Hartmann M. The bacterial Lectin FimH, a target for drug discovery – carbohydrate inhibitors of type 1 fimbriae-mediated bacterial adhesion // Eur. J. Org. Chem. 2011. Р. 3583–3609.

3. Bernardi A. Multivalent glycoconjugates as anti-pathogenic agents // Chem. Soc. Rev. 2013. № 42. Р. 4709–4727.

4. Gostenin V.B., Shchelik I.S., Sebyakin Yu.L. Synthesis and optimization of octavalent bolaamphiphile preparation with terminal D-mannose residues. // Tonkie khimicheskie tekhnologii (Fine Chemical Technologies). 2015. V. 10. № 5. Р. 39–43. (in Russ.).

5. Kiessling L.L., Gestwicki J.E., E. Laura. Strong. Synthetic multivalent ligands as probes of signal transduction // Angew. Chem. Int. Ed. Engl. 2006. № 45. Р. 2348–2368.

6. Kaplanek R. Three-fold polyfluoroalkylated amines and isocyanates based on tris(hydroxymethyl) aminomethane (TRIS) // J. Fluorine Chem. 2007. № 128. Р. 179–183.

7. Guryeva L.Yu., Bolsheborodova A.K., Yu.L. Sebiakin. Synthesis of carbohydrate-containing components of lipid transport systems of directional lipid transport systems of directed action by the "ClickChemistry" method // Vestnik MITHT (Fine Chemical Technologies). 2009. V. 4. № 6. P. 62–67. (in Russ.).

8. Golovanov A.B., Ganina K.D., Groza N.V., Eremin S.V., Myagkova G.I. Synthesis of the 6-(5z,8z)- tetradecadienoic and (7z,10z)-hexadecadienoic polyene fatty acids // Chem. Nat. Comp. 2015. № 51. Р. 26–30.

9. Palagin I.S., Sukhorukova M.V., Dehnich A.V., Eidelshtein M.V., Grinev A.V., Perepanova T.S., Kozlov R.S. Complicated out-of-hospital urinary tract infections in adult patients in Russia // Clinicheskay microbiologiya i antimicrobnaya khimioterapiya. (Clinical Microbiology and Antimicrobial Chemotherapy). 2014. V. 16. № 1. P. 39–56. (in Russ.).


For citations:

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.)

Views: 284

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