Chemotactic peptides: fMLF-OMe analogues incorporating proline-methionine chimeras as N-terminal residue.
The new fMLF analogues 1-4, incorporating chimeric S-proline-methionine residues (namely the homochiral cis-4(S)-methylthio-(S)-proline (10) and the heterochiral trans-4(R)-methylthio-(S)-proline) (17) in place of the native S-methionine, have been prepared; their solution conformation and activity as agonists or antagonists of formylpeptide receptors have been studied. In addition to peptides 1-4, which maintain the Met gamma-thiomethyl-ether function, the analogues Boc-PLF-OMe (18) and For-PLF-OMe (19) devoid, as compared with 1-4, of position 1 side chain, have been synthesized and their activity examined.
Mollica
Adriano
A
Dipartimento di Studi Farmaceutici and Istituto di Chimica Biomolecolare, CNR Sezione di Roma, Università di Roma La Sapienza, P.le A.Moro, 00185 Rome, Italy.
Paradisi
Mario Paglialunga
MP
Varani
Katia
K
Spisani
Susanna
S
Lucente
Gino
G
D003594:Cytoplasmic Granules / Q000187:drug effects / Q000201:enzymology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008715:Methionine / Q000737:chemistry*; D008968:Molecular Conformation; D009113:Muramidase / Q000187:drug effects; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D009842:Oligopeptides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013844:Thiazoles
D009842:Oligopeptides; D013844:Thiazoles; C511147:trans-4(R)-methylthio-(S)-proline; D009240:N-Formylmethionine Leucyl-Phenylalanine; D011392:Proline; D008715:Methionine; D009113:Muramidase