Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin.
Indole-3-acetic acid is an indispensable 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.
Ilić
Nebojsa
N
Ruder Bosković Institute, p.p. 180, HR-10002 Zagreb, Croatia.
Habus
Ivan
I
Barkawi
Lana S
LS
Park
Seijin
S
Stefanić
Zoran
Z
Kojić-Prodić
Biserka
B
Cohen
Jerry D
JD
Magnus
Volker
V
D000818:Animals; D000911:Antibodies, Monoclonal / Q000737:chemistry; D001710:Biotin / Q000737:chemistry; D019921:Biotinylation; D002417:Cattle; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D007118:Immunoassay; D007210:Indoleacetic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D011485:Protein Binding; D012710:Serum Albumin, Bovine / Q000737:chemistry
D000911:Antibodies, Monoclonal; D007210:Indoleacetic Acids; D012710:Serum Albumin, Bovine; D001710:Biotin