Modifications of the amide bond at position 3 in fMLP analogs select neutrophil functions.
The formylpeptides formyl-L-methionyl-L-leucyl-L-N-methylphenylalanine methyl ester 1, formyl-L-methionyl-L-leucyl-L-2-oxy-3-phenylpropionic acid methyl ester 2 and formyl-L-methionyl-L-leucyl-L-2-aminoxy-3-phenylpropionic acid methyl ester 3 were synthesized to investigate the role of the amide bond at position 3 in biological activity in human neutrophiles. Our results indicate that this amide bond is required for optimal chemotactic activity, but not for superoxide anion production.
Spisani
S
S
University of Ferrara, Italy.
Breveglieri
A
A
Fabbri
E
E
Vertuani
G
G
Rizzuti
O
O
Cavicchioni
G
G
D001665:Binding Sites; D001667:Binding, Competitive; D002634:Chemotaxis, Leukocyte / Q000187:drug effects / Q000502:physiology; D004151:Dipeptides / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009113:Muramidase / Q000378:metabolism; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D009504:Neutrophils / Q000187:drug effects* / Q000378:metabolism / Q000502:physiology; D010666:Phenylpropionates / Q000737:chemistry / Q000494:pharmacology*; D013481:Superoxides / Q000378:metabolism
D004151:Dipeptides; D010666:Phenylpropionates; C105984:formyl-methionyl-leucyl-2-aminooxy-3-phenylpropionic acid methyl ester; C105983:formyl-methionyl-leucyl-2-oxy-3-phenylpropionic acid methyl ester; C105982:formyl-methionyl-leucyl-N-methylphenylalanine methyl ester; D013481:Superoxides; D009240:N-Formylmethionine Leucyl-Phenylalanine; D009113:Muramidase