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.
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', P.le A. Moro 5, 00185 Rome, Italy.
Lucente
Gino
G
Nalli
Marianna
M
Pagani Zecchini
Giampiero
G
Paglialunga Paradisi
Mario
M
Varani
Katia
K
Spisani
Susanna
S
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