Beta-peptido sulfonamides: for-Met-Leu-Phe-OMe analogues containing taurine and chiral beta-amino-ethanesulfonic acid residues.
A series of new beta-peptido sulfonamides, related to the chemotactic tripeptide fMLF-OMe, has been synthesized. The examined 1a,b-7a,b models contain the achiral -HN-(CH(2))(2)-SO(2)- taurine (Tau) residue or the chiral -HN-CH(nBu)-CH(2)-SO(2)- and -HN-CH(iBu)-CH(2)-SO(2)- residues, corresponding to the beta-aminocarboxylic acid counterparts beta(3)-HNle and beta(3)-HLeu, respectively. The biological activity of the new analogues has been determined on human neutrophils and compared with that of the reference ligand as well as that of the previously studied related models. The results are analyzed in terms of structure-activity relationships. The conformational preferences of the new tripeptides 1b and 2b, containing a central chiral beta-amino-ethanesulfonic acid residue, have also been discussed.
Giordano
Cesare
C
Istituto di Chimica Biomolecolare del CNR, Sezione di Roma c/o Dipartimento di Studi Farmaceutici, Università degli Studi di Roma La Sapienza, Piazzale A. Moro 5, 00185 Rome, Italy.
Nalli
Marianna
M
Paradisi
Mario Paglialunga
MP
Sansone
Anna
A
Lucente
Gino
G
Spisani
Susanna
S
D002633:Chemotaxis / Q000187:drug effects / Q000502:physiology; D004305:Dose-Response Relationship, Drug; D004983:Ethanolamines / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D009504:Neutrophils / Q000166:cytology / Q000187:drug effects; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology; D013451:Sulfonic Acids / Q000737:chemistry* / Q000494:pharmacology; D013654:Taurine / Q000737:chemistry* / Q000494:pharmacology
D004983:Ethanolamines; D013449:Sulfonamides; D013451:Sulfonic Acids; D013654:Taurine; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester