Abstract
New glycyrrhizic acid (GA) conjugates were synthesized with the use of tert-butyl esters of amino acids or benzyl esters of dipeptides; they contained two residues of L-amino acids (Met, Phe, Pro, and Ile or dipeptides Gly-Leu and Gly-Phe). Activation of GA carboxy groups was carried out with the help of N-hydroxysuccinimide, N,N′-dicyclohexylcarbodiimide, or N-hydroxybenzotriazole with dicyclohexylcarbodiimide. A proline-containing GA derivative is a low-toxic substance; it raises the level of agglutinins by 3.7 times in the blood of mice and 3 times that of hemolysins compared with the control. Dipeptide GA derivatives possess an expressed anti-HIV-1 activity in cultures of MT-4 cells and are 90-70 times less cytotoxic than azidothymidine. The selectivity index of the compounds exceeds those of GA by 110 and 34 times, respectively.
Key words: glycyrrhizic acid, conjugates, amino acids, dipeptides, synthesis, immunostimulating and anti-HIV-1 activity
Abbreviations
- AA
amino acid component
- CC
column chromatography
- DCC
N,N′-dicyclohexylcarbodiimide
- GA
glycyrrhizic acid
- HIV
human immunodeficiency virus
- HONSu
N-hydroxysuccinimide
- HOBt
N-hydroxybenzotriazole
- RT
reverse transcriptase
- SE
sheep erythrocytes
Footnotes
Original Russian Text © L.A. Baltina, Jr., R.M. Kondratenko, L.A. Baltina, N.Z. Baschenko, O.A. Pl’yasunova, 2009, published in Bioorganicheskaya Khimiya, 2009, Vol. 35, No. 4, pp. 563–571.
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