Naslov
Novel adamantylglycyl derivative of peptidoglycan monomer

Autori
Šporec, Vesna ; Ljevaković, Đurđica ; Halassy Špoljar, Beata ; Frkanec, Ruža ; Vranešić, Branka ; Krstanović, Marina ; Tomašić, Jelka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Drugi hrvatski kongres farmacije s međunarodnim sudjelovanjem, Knjiga sažetaka / Jandrijević-Mladar Takač, M; Jurišić, R; Vuković, J - Zagreb : Farmaceutsko-biokemijski fakultet Sveučilišta u Zagrebu, 2001, 132-132

Skup
Drugi hrvatski kongres farmacije s međunarodnim sudjelovanjem

Mjesto i datum
Cavtat, Hrvatska, 31.05.2001. - 03.06.2001

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Sažetak
Chemical modifications of a biologically active compound could eventually result in a new phareaceutical entity with better or enriched biological activity. Peptidoglycan monomer (PGM, PLIVA) is a natural compound originating from the cell wall peptidoglycan of the Brevibacterium divaricatum. It has been shown that PGM exhibits strong immunomodulating, antitumor, and antimetastatic activities1, and transiently inhibits the function of drug-metabolizing enzymes in the liver2. In order to modify biological activity of PGM two derivatives were synthesysed: N-terc-butyloxycarbonyl-L-tyrozyl-PGM3 and (adamant-1-yl)-acetyl-PGM. Neither of them affected the biological properties of the parent compound and both are good substrates for N-acetylmuramyl-L-alanine amidase4 present in mammalian blood, which cleaves the peptidoglycans giving the disacharide and respective peptides. Novel synthetic analogue of immunomodulatory PGM, N-(terc-butyloxycarbonyl)-D,L-(adamant-2-yl)-glycyl-PGM, was prepared by covalent coupling of the N-(terc-butyloxycarbonyl)-D,L-(adamant-2-yl)-glycine to the free amino group of diaminopimelic acid in parent PGM molecule. The product was isolated by column chromatography on Sephadex LH 20 in 50% ethanol followed by silicagel column (0,063-0,2 mm) in n-propanol/ethylacetate/water (1/1/1). The structure of the new compound was confirmed by mass spectrometry, 1H and 13C NMR and acid hydrolysis. Lipophilic supstituent on amino group in peptapeptide portion of PGM didn’t affect the susceptibility of new derivative to the hydrolysis with N-acetylmuramyl-L-alanine amidase. New derivative is currently under investigation for its immunostimulatory activity, in vivo, in an experimental model in mice, using ovalbumin as an antigen, as described in our previous paper1. (1J. Tomašić et al. Vaccine 18 (2000)1236-1243, 2A. Trešćec et al. Int J Immunopharmacol 9 (1987) 371-378, 3 B. Vranešić et al. Clin. Chim. Acta 202 (1991) 23-28, 4 Đ. Ljevaković et al. Biorg. Med. Chem. 8 (2000) 2441-2449.)

Izvorni jezik
Engleski

Znanstvena područja
Kliničke medicinske znanosti

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