Naslov
Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin

Autori
Ilić, Nebojša ; Habuš, Ivan ; Barkawi, Lana S. ; Park, Seijin ; Štefanić, Zoran ; Kojić-Prodić, Biserka ; Cohen, Jerry D. ; Magnus, Volker

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 13 (2005), 9; 3229-3240

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Auxin; indole-3-acetic acid; 5-(2-aminoethyl)indole-3-acetic acid; 6-(2-aminoethyl)indole-3-acetic acid; synthesis; molecular structure; hapten; monoclonal antibody; biotin conjugate

Sažetak
Indole-3-acetic acid is an indispensible hormone (auxin) in plants and an important metabolite in humans, animals and microorganisms. Here we introduce its 5- and 6-(2-aminoethyl)-derivatives for use in the design of novel research tools, such as immobilized and carrier-linked forms of indole-3-acetic acid and its conjugates with biochemical tags or biocompatible molecular probes. The aliphatic nitrogens of 5- and 6-(2-aminoethyl)indole were acetylated and the products were converted to the corresponding 3-(N, N-dimethylamino)methyl derivatives (gramines). These were reacted with cyanide. Saponification of the resulting acetonitriles was accompanied by N-deprotection to yield 5- and 6-(2-aminoethyl)indole-3-acetic acids. The latter were chemically stable and could be linked, via their amino groups, and without prior protection of their carboxyl moieties, to bovine serum albumin and to biotin, including appropriate spacer modules. One of the protein conjugates was used to elicit the formation of monoclonal antibodies which were evaluated using the biotin conjugates in an enzyme-linked immunosorbent assay employing streptavidin-coupled alkaline phosphatase, and thus shown to recognize predominantly the indole-3-acetic acid moiety.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija

POVEZANOST RADA