Pseudopeptides containing the 2-hydrazonoacyl fragment: analogs of the chemotactic agent HCO-Met-Leu-Phe-OMe.
In order to further examine the properties of pseudopeptides containing the 2-hydrazonoacyl fragment, two new series of analogs of the prototypical chemotactic N-formyl-tripeptide HCO-Met-Leu-Phe-OMe were designed and synthesized. The first group contains the new fragment as the N-terminal residue and is represented by the N-aryl derivatives p-Cl-C6H4-NH-N=C(R)-CO-Leu-Phe-OMe (2 and 3) and by the corresponding N-aroyl analogs p-CH3-C6H4-CO-NH-N=C(R)-CO-Leu-Phe-OMe (4). The second group contains the new fragment in place of the central Leu residue and is represented by compounds HCO-Xaa-NH-N=C(R)-CO-Phe-OMe (7a and 7b) where Xaa is Nle and Met, respectively. The conformational and biochemical properties of the new products were examined.
Torrini
I
I
Dipartimento di Studi Farmaceutici and Centro di Studio per la Chimica del Farmaco del CNR, Università 'La Sapienza', Rome, Italy.
Nalli
M
M
Paglialunga Paradisi
M
M
Pagani Zecchini
G
G
Lucente
G
G
Spisani
S
S
D001671:Biochemistry / Q000379:methods; D002478:Cells, Cultured; D002630:Chemotactic Factors / Q000737:chemistry* / Q000494:pharmacology*; D002634:Chemotaxis, Leukocyte / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D006801:Humans; D006834:Hydrazines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D009842:Oligopeptides / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism
D002630:Chemotactic Factors; D006834:Hydrazines; D009842:Oligopeptides; D013481:Superoxides; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester