Biscarbamate analogues of the chemotactic tripeptide fMLF-OMe.
Based on the sequence of the prototypical chemotactic tripeptide HCO-Met-Leu-Phe-OH (fMLF) and by taking into account the versatility shown by its N-terminal carbamate analogues, the new biscarbamates MeOCO-Met-Leu-gPhe-COOMe (2) and Boc-Met-Leu-gPhe-COOMe (4) were synthesized. These two new ligands are characterized by the presence of a gem-diamino residue (gPhe) replacing the C-terminal Phe and a carbamate functionality positioned at both the ends of the molecule. The activity of the two new compounds has been determined on human neutrophils and compared to that shown by the corresponding N-terminal monocarbamates MeOCO-Met-Leu-Phe-OMe (1) and Boc-Met-Leu-Phe-OMe (3).
Zecchini
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GP
Centro di Studio per la Chimica del Farmaco del CNR, c/o Dipartimento di Studi Farmaceutici, Università degli Studi di Roma La Sapienza, Rome, Italy.
Paradisi
M P
MP
Torrini
I
I
Nalli
M
M
Lucente
G
G
Spisani
S
S
D002219:Carbamates / Q000737:chemistry; D002630:Chemotactic Factors / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D009504:Neutrophils / Q000502:physiology*; D010455:Peptides / Q000737:chemistry
D002219:Carbamates; D002630:Chemotactic Factors; D010455:Peptides; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester