title: Synthesis and biological evaluation of guanidino compounds endowed with subnanomolar affinity as competitive inhibitors of maize polyamine oxidase.
abstract: Previous studies on agmatine and its derivatives suggested that the presence of hydrophobic groups on the guanidine moiety was a crucial key for inhibitory activity of maize polyamine oxidase. Accordingly, new lipophilic agmatine and iminoctadine derivatives were synthesized and tested for their ability to inhibit this enzyme. Several compounds showed an affinity in the nanomolar range, while a cyclopropylmethyl derivative of iminoctadine was found to be the most potent inhibitor of maize polyamine oxidase reported so far (Ki = 0.08 nM).
authors: Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via Alcide de Gasperi 2, I-53100 Siena, Italy.
authors: Fabrizio
authors: F
authors: Manetti
authors: Alessandra
authors: A
authors: Cona
authors: Lucilla
authors: L
authors: Angeli
authors: Claudia
authors: C
authors: Mugnaini
authors: Francesco
authors: F
authors: Raffi
authors: Caterina
authors: C
authors: Capone
authors: Elena
authors: E
authors: Dreassi
authors: Alessandra Tania
authors: AT
authors: Zizzari
authors: Alessandra
authors: A
authors: Tisi
authors: Rodolfo
authors: R
authors: Federico
authors: Maurizio
authors: M
authors: Botta
mesh_terms: D000376:Agmatine / Q000031:analogs & derivatives* / Q000494:pharmacology; D001665:Binding Sites; D001667:Binding, Competitive; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D006146:Guanidines / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D000587:Oxidoreductases Acting on CH-NH Group Donors / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D003313:Zea mays / Q000201:enzymology*; D000097667:Polyamine Oxidase
chemical_list: D000376:Agmatine; D004791:Enzyme Inhibitors; D006146:Guanidines; D000587:Oxidoreductases Acting on CH-NH Group Donors; D000097667:Polyamine Oxidase; C012343:guazatine