The importance of the peptide bond at position 2 in HCO-Met-Leu-Phe-OMe analogues as shown by studies on human neutrophils.
The formylpeptides formyl-methionyl-N-methylleucyl-phenylalanine methyl ester [for-Met-(NMe)Leu-Phe-OMe] 1, formyl-methionyl-2-aminotetralin-2-carboxyl-phenylalanine methyl ester [for-Met-Atc-Phe-OMe] 2, formyl-methionyl-1,2,3,4-tetrahydroisoquinoline-3-carboxyl-phenylalanine methyl ester [for-Met-Tic-Phe-OMe] 3 and formyl-methionyl-2-aminoxy-4-methylvaleryl-phenylalanine methyl ester [for-Met-OLeu-Phe-OMe] 4 were synthesized in order to investigate the role of the amide bond at position 2 on biological activities on human neutrophils. Only analogue 2, which keeps the NH group at position 2, was found to retain activity though sterically encumbered.
Cavicchioni
G
G
Department of Pharmaceutical Sciences, University of Ferrara, Italy.
Breveglieri
A
A
Boggian
M
M
Vertuani
G
G
Reali
E
E
Spisani
S
S
D002465:Cell Movement / Q000187:drug effects; D002633:Chemotaxis / Q000187:drug effects; D006801:Humans; D009113:Muramidase / Q000737:chemistry / Q000187:drug effects; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009504:Neutrophils / Q000737:chemistry* / Q000187:drug effects* / Q000378:metabolism; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism
D010455:Peptides; D013481:Superoxides; C080504:formyl-methionyl-delta(Z)-dehydroleucyl-phenylalanine methyl ester; D009240:N-Formylmethionine Leucyl-Phenylalanine; D009113:Muramidase