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

Crosbi ID106361
Bib IRB ID152017
Year2005
StatusObjavljeno
Typeprilog u časopisu
Subtypeizvorni znanstveni rad
AuthorsIlić, Nebojša ; Habuš, Ivan ; Barkawi, Lana S. ; Park, Seijin ; Štefanić, Zoran ; Kojić-Prodić, Biserka ; Cohen, Jerry D. ; Magnus, Volker
JournalBioorganic & medicinal chemistry
Volume13
Issue9
Pages3229-3240
ISSN0968-0896
EISSN1464-3391
Titles

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

Abstracts
en original

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.

Keywords

en original 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

Authors
Institutions
Disciplines
Citations
Ilić, Nebojša ; Habuš, Ivan ; Barkawi, Lana S. ; Park, Seijin ; Štefanić, Zoran ; Kojić-Prodić, Biserka ; Cohen, Jerry D. ; Magnus, Volker
Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin // Bioorganic & medicinal chemistry, 13 (2005), 9; 3229-3240-x
Indexing

Current Contents Connect (CCC) Medline Scopus Web of Science Core Collection, SCI-Exp, SSCI & A&HCI (WoSCC-SCI-Exp, SSCI, A&HCI) Web of Science Core Collection, Science Citation Index Expanded (WoSCC-SCI-Exp)