Synthesis of the hydrocarbon components of the lipid transport systems using click-chemistry
Abstract
Neoglycolipids based on azide containing D-lactose derivative and di-esters of L-glutamic acid with terminal acetylene group were synthesized by click-chemistry technology. Prepared compounds could be utilized in targeted drug delivery systems.
About the Authors
L. Yu. Guryeva
Moscow Technological University (Institute of Fine Chemical Technologies), 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
A. К. Bolsheborodova
Moscow Technological University (Institute of Fine Chemical Technologies), 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
Y. L. Sebyakin
Moscow Technological University (Institute of Fine Chemical Technologies), 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
References
1. Буданова, У. А. Структурно-функциональное разнообразие искусственных мембран на основе катионных липопептидов / У. А. Буданова, Л. Ю. Гурьева, Ю. Л. Себякин // Биол. мембраны. - 2007. - Т. 24, № 3. - С. 273-279.
2. Huisgen, R. In: «1.3-Dipolar Cycloadditional Chemistry»/ R. Huisgen. - NY : Wiley, 1984. - 176 p.
3. Kolb, H. C. Click chemistry: diverse chemical function from a few good reactions / H. . Kolb, M. G. Finn, K. B. Sharpless // Angew. Chem. Int. Ed. - 2001. - Vol. 40. - P. 2004-2021.
4. Tornoe, C. W. Peptidotriazoles on solid phase: [1.2.3]-triazoles by regiospecific copper(I)-catalyzed 1.3-dipolar cycloadditions of terminal alkynes to azides / C. W. Tornoe, C. Christensen, M. Meldal // J. Org. Chem. - 2002. - Vol. 67. - P. 3057-3062.
5. Kolb, H. C. The growing impact of click chemistry on drug discovery / H. C. Kolb, B. Sharpless // Drug Discov. Today. - 2003. - Vol. 8. - P. 1128-1137.
6. Bock, V. D. CuI-catalyzed alkyne-azide «click» cycloadditions from a mechanistic and synthetic perspective / V. D. Bock, H. Hiemstra, J. H. van Maarseveen // Eur. J. Chem. - 2006. - P. 51-68.
7. Hein, C. D. Click chemistry, a powerful tool for pharmaceutical sciences / C. D. Hein, Xin-Ming Liu, Dong Wang // Pharm. Res. - 2008. - Vol. 25, № 10. - P. 2216-2230.
8. 4-Cyclohexyl-1-substituted-4H-[1.2.4]triazolo[4.3-a]quinazolin-5-ones: novel class of H1-antihistaminic agents / V. Alagarsamy [et al.] // Chem. Biol. Drug Des. - 2007. - Vol. 70. - P. 158-163.
9. Synthesis and antibiotic activity of a small molecules library of 1.2.3-triazole derivatives / M. Aufort [et al.] // Bioorg. Med. Chem. Lett. - 2008. - Vol. 18. - P. 1195-1198.
10. Gaucheron, J. In vitro gene transfer with a novel galactosylated spermine bolaamphiphile / J. Gaucheron, C. Santaella, P. Vierling // Bioconjugate Chem. - 2001. - Vol. 12, № 4. - P. 569-575.
11. Preparation and applications of 2-bromoethyl glycosides: synthesis of spacer-arm glycosides and agglutination inhibitors / J. Dahmén, T. Frejd, G. Magnusson, G. Noori // Carbohydr. Res. - 1982. - Vol. 111. - P. 1-4.
12. Reineke, T. M. Carbohydrate size and its distance from charge centers bioconjugate chemistry / T. M. Reineke, M. E. Davis // Bioconjugate Chem. - 2003. - Vol. 14. - P. 247-254.
13. Себякин, Ю. Л. Синтез амфифильных производных L-серина / Ю. Л. Себякин, Н. Л. Федякова, Е. А. Рунова // Биоорган. химия. - 1994. - №. 20. - C. 1101-1114.
14. Кочетков, Н. К. Методы химии углеводов / Н. К. Кочетков. - М. : Мир, 1967. - 428 с.
For citation:
Guryeva L.Yu., Bolsheborodova A.К., Sebyakin Y.L. Synthesis of the hydrocarbon components of the lipid transport systems using click-chemistry. Fine Chemical Technologies. 2009;4(6):61-66. (In Russ.)
Views: 58
Email this article 