Synthesis and activity of HCO-Met-Leu-Phe-OMe analogues containing beta-alanine or taurine at the central position.
New synthetic analogues of the chemotactic N-formyltripeptide HCO-Met-Leu-Phe-OMe have been synthesized. The reported new models, namely Boc-Met-beta-Ala-Phe-OMe (1), HCO-Met-beta-Ala-Phe-OMe (2), Boc-Met-Tau-Phe-OMe (3), HCO-Met-Tau-Phe-OMe (4) and HCl.Met-Tau-Phe-OMe (5), are characterized by the presence at the central position of a residue of beta-alanine or 2-aminoethanesulfonic acid (taurine) replacing the native L-leucine. Whereas tripeptides 1 and 2 have been found quite inactive as chemoattractants, all the three models containing the Tau residue exhibit a remarkable activity. Superoxide anion production and lysozyme release have been also evaluated and the biological results are discussed together with the conformational preferences of the examined models.
Istituto di Chimica Biomolecolare del CNR, Sezione di Roma c/o, Dipartimento di Studi Farmaceutici, Università degli Studi di Roma 'La Sapienza', P.le A. Moro 5, 00185 Rome, Italy.
Cesare
C
Giordano
Gino
G
Lucente
Marianna
M
Nalli
Giampiero
G
Pagani Zecchini
Mario
M
Paglialunga Paradisi
Katia
K
Varani
Susanna
S
Spisani
D004305:Dose-Response Relationship, Drug; D006801:Humans; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D011485:Protein Binding / Q000187:drug effects / Q000502:physiology; D013654:Taurine / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D015091:beta-Alanine / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
D015091:beta-Alanine; D013654:Taurine; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester