Modified chemotactic peptides: synthesis and biological activity of HCO-Met-delta ZLeu-delta ZPhe-OMe.
For-Met-delta ZLeu-delta ZPhe-OMe (3) has been synthesized as a new analogue of the prototypical chemotactic agent For-Met-Leu-Phe-OMe (fMLP-OMe). Compound 3 is characterized by presence of two consecutive alpha,beta-didehydro amino acid residues [delta ZLeu = (Z)-alpha,beta-didehydroleucine; delta ZPhe = (Z)-alpha,beta- didehydrophenylalanine] located at the central and C-terminal position, respectively. When tested on human neutrophils the N-formyltripeptide 3, although less active than the parent, is able to induce chemotaxis, superoxide anion production and lysozyme release. The activity of 3 has been compared to that of related fMLP-OMe analogues containing a single delta ZPhe residue located at the C-terminal position.
Dipartimento di Studi Farmaceutici, Università La Sapienza, Roma.
G
G
Pagani Zecchini
I
I
Torrini
M
M
Paglialunga Paradisi
G
G
Lucente
S
S
Spisani
D000595:Amino Acid Sequence; D002630:Chemotactic Factors / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D008969:Molecular Sequence Data; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
D002630:Chemotactic Factors; C080504:formyl-methionyl-delta(Z)-dehydroleucyl-phenylalanine methyl ester; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester