Systematic N-methylation of oxytocin: Impact on pharmacology and intramolecular hydrogen bonding network

• Published in: Bioorganic & medicinal chemistry Vol. 24; no. 16; pp. 3513 - 3520
• Main Authors: Sciabola, Simone, Goetz, Gilles H., Bai, Guoyun, Rogers, Bruce N., Gray, David L., Duplantier, Allen, Fonseca, Kari R., Vanase-Frawley, Michelle A., Kablaoui, Natasha M.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.08.2016; Elsevier
• Subjects: Biochemistry & Molecular Biology; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Cyclic peptide; Hidden polarity; Hydrogen Bonding; Intramolecular hydrogen bond; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Methylation; NMR; Oxytocin; Oxytocin - chemistry; Peptide; Pharmacology & Pharmacy; Physical Sciences; Polarity; Science & Technology; SFC; Structure-Activity Relationship; Temperature; Hidden polarity; SFC; NMR; Cyclic peptide; Oxytocin; SPPS; Polarity; FLIPR; Intramolecular hydrogen bond; Hydrogen bonding; Peptide; Mpa; PERMEABILITY; HUMANS; INTRANASAL DELIVERY; CONFORMATION; CYCLIC-PEPTIDES; HIGHLY POTENT ANALOGUE; PEPTIDE-HORMONE-OXYTOCIN; ORAL BIOAVAILABILITY; DIMETHYL-SULFOXIDE

[Display omitted] Oxytocin (OT) is a peptide hormone agonist of the OT receptor (OTR) that plays an important role in social behaviors such as pair bonding, maternal bonding and trust. The pharmaceutical development of OT as an oral peptide therapeutic has been hindered historically by its unfavorab...