Microbial growth-promotion activity of 3-hydroxymonoazine- and N-hydroxydiazine-type heterocycles.
Three 3-hydroxymonoazine- and three N-hydroxydiazine-type heterocycles were tested whether they act as artificial siderophores toward Aureobacterium flavescens JG-9 (ATCC No. 25091). Among them, 1-hydroxy-3,5,6-trimethyl-2(1H)-pyrazinone (3) showed the highest growth-promotion activity comparable to desferrioxamine B (DFB), a natural trihydroxamate siderophore, at 48.5 microM or above, followed by 1-hydroxy-5,6-dimethyl-2(1H)-pyrazinone (2), 1-hydroxy-4,6-dimethyl-2(1H)-pyrimidinone (1), and 3-hydroxy-2-methyl-1-phenyl-4(1H)-pyridinone (6), while 3-hydroxy-1,2-dimethyl-4(1H)-pyridinone (5) did not show the bioactivity. These results are the first examples of N-hydroxydiazine-type heterocycles acting as artificial siderophores for A. flavescens JG-9.
Saito
Ryota
R
Department of Applied Chemistry, Faculty of Engineering, Seikei University, 3-3-1, Kichijoji-kitamachi, Musashino-shi, Tokyo 180-8633, Japan.
Ghosh
Kallol K
KK
Harada
Kazuo
K
Katoh
Akira
A
D004305:Dose-Response Relationship, Drug; D006093:Gram-Positive Asporogenous Rods / Q000254:growth & development*; D011719:Pyrazines / Q000494:pharmacology*; D011728:Pyridones / Q000494:pharmacology*; D011744:Pyrimidinones / Q000494:pharmacology*; D017262:Siderophores / Q000494:pharmacology*; D013268:Stimulation, Chemical; D013329:Structure-Activity Relationship
D011719:Pyrazines; D011728:Pyridones; D011744:Pyrimidinones; D017262:Siderophores