1093754-92-7Relevant academic research and scientific papers
Influences of Histidine-1 and Azaphenylalanine-4 on the Affinity, Anti-inflammatory, and Antiangiogenic Activities of Azapeptide Cluster of Differentiation 36 Receptor Modulators
Chignen Possi, Kelvine,Mulumba, Mukandila,Omri, Samy,Garcia-Ramos, Yesica,Tahiri, Houda,Chemtob, Sylvain,Ong, Huy,Lubell, William D.
, p. 9263 - 9274 (2017/11/30)
Azapeptide analogues of growth hormone releasing peptide-6 (GHRP-6) exhibit promising affinity, selectivity, and modulator activity on the cluster of differentiation 36 receptor (CD36). For example, [A1, azaF4]- and [azaY4
Azapeptide analogues of the growth hormone releasing peptide 6 as cluster of differentiation 36 receptor ligands with reduced affinity for the growth hormone secretagogue receptor 1a
Proulx, Caroline,Picard, émilie,Boeglin, Damien,Pohankova, Petra,Chemtob, Sylvain,Ong, Huy,Lubell, William D.
scheme or table, p. 6502 - 6511 (2012/10/08)
The synthetic hexapeptide growth hormone releasing peptide-6 (GHRP-6) exhibits dual affinity for the growth hormone secretagogue receptor 1a (GHS-R1a) and the cluster of differentiation 36 (CD36) receptor. Azapeptide GHRP-6 analogues have been synthesized, exhibiting micromolar affinity to the CD36 receptor with reduced affinity toward the GHS-R1a. A combinatorial split-and-mix approach furnished aza-GHRP-6 leads, which were further examined by alanine scanning. Incorporation of an aza-amino acid residue respectively at the d-Trp2, Ala3, or Trp4 position gave aza-GHRP-6 analogues with reduced affinity toward the GHS-R1a by at least a factor of 100 and in certain cases retained affinity for the CD36 receptor. In the latter cases, the d-Trp2 residue proved important for CD36 receptor affinity; however, His1 could be replaced by Ala1 without considerable loss of binding. In a microvascular sprouting assay using a choroid explant, [azaTyr4]-GHRP-6 (15), [Ala1, azaPhe 2]-GHRP-6 (16), and [azaLeu3, Ala6]-GHRP-6 (33) all exhibited antiangiogenic activity.
Exploring side-chain diversity by Submonomer solid-phase aza-peptide synthesis
Sabatino, David,Proulx, Caroline,Klocek, Sophie,Bourguet, Carine B.,Boeglin, Damien,Ong, Huy,Lubell, William D.
supporting information; experimental part, p. 3650 - 3653 (2011/02/25)
Image Presented Submonomer synthesis of aza-peptides featuring regioselective alkylation of peptide-bound aza-Gly residues provided ten aza-analogues of the Growth Hormone Releasing Peptide-6 (GHRP-6) in 15-42% yield and purity generally g90%. Circular dichroism demonstrated that azaPhe-peptide 7a induced a β-turn conformation which may be responsible for its 1000-fold improvement in GHRP-6 selectivity for the CD36 receptor. This versatile method for making aza-peptides avoids solution-phase hydrazine synthesis and is well suited for studying side-chain-activity relationships of biologically active peptides.
