Synthesis and biological evaluation of a novel pyroglutamyl-modified TRH analogue

The TRH analogue 3, incorporating the ( S)-isothiazolidine-1,1-dioxide-3-carboxylic acid ( 1) moiety in place of the native l-pyroglutamic acid (pGlu) residue, has been synthesized and fully characterized by 1H and 13C NMR. The effects of replacing pGlu with its sulphonamido counterpart on biologica...

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Veröffentlicht in:	Farmaco (Società chimica italiana : 1989) 2002-06, Vol.57 (6), p.479-486
Hauptverfasser:	Brunetti, L., Cacciatore, I., Di Stefano, A., Duprè, S., Giorgi, A., Luisi, G., Michelotto, B., Orlando, G., Pinnen, F., Recinella, L., Sozio, P., Spirito, A.
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Biological and medical sciences Cattle Cells, Cultured Dopamine - secretion Dose-Response Relationship, Drug Hormones. Endocrine system Male Medical sciences Nuclear Magnetic Resonance, Biomolecular Pharmacology. Drug treatments Pituitary Gland, Anterior - drug effects Pituitary Gland, Anterior - metabolism Prolactin - secretion Pyroglutamic acid Pyroglutamyl peptidases Pyroglutamyl-Peptidase I - metabolism Pyrrolidonecarboxylic Acid - chemical synthesis Pyrrolidonecarboxylic Acid - chemistry Pyrrolidonecarboxylic Acid - pharmacology Rats Rats, Wistar Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization - methods Sulphonamidopeptides Synaptosomes Thyrotropin-releasing hormone Thyrotropin-Releasing Hormone - analogs & derivatives Thyrotropin-Releasing Hormone - chemical synthesis Thyrotropin-Releasing Hormone - pharmacology
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Beschreibung
Zusammenfassung:	The TRH analogue 3, incorporating the ( S)-isothiazolidine-1,1-dioxide-3-carboxylic acid ( 1) moiety in place of the native l-pyroglutamic acid (pGlu) residue, has been synthesized and fully characterized by 1H and 13C NMR. The effects of replacing pGlu with its sulphonamido counterpart on biological activity have been investigated. This peptide, which is significantly stabilized towards hydrolysis by pyroglutamyl peptidase type I (PP I, EC 3.4.19.3), has shown to maintain in vitro prolactin-releasing activity.
ISSN:	0014-827X 1879-0569
DOI:	10.1016/S0014-827X(02)01232-6