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Titolo:
Magnesium and biological activity of oxytocin analogues modified on aromatic ring of amino acid in position 2
Autore:
Slaninova, J; Maletinska, L; Vondrasek, J; Prochazka, Z;
Indirizzi:
Acad Sci Czech Republ, Inst Organ Chem & Biochem, Dept Peptide Biochem, CR-16610 Prague 6, Czech Republic Acad Sci Czech Republ Prague Czech Republic 6 0 Prague 6, Czech Republic Acad Sci Czech Republ, Inst Organ Chem & Biochem, Ctr Complex Mol Syst & Biomol, Prague, Czech Republic Acad Sci Czech Republ Prague Czech Republic mol, Prague, Czech Republic Acad Sci Czech Republ, Inst Organ Chem & Biochem, Dept Peptide Synthesis, Prague, Czech Republic Acad Sci Czech Republ Prague Czech Republic sis, Prague, Czech Republic
Titolo Testata:
JOURNAL OF PEPTIDE SCIENCE
fascicolo: 8, volume: 7, anno: 2001,
pagine: 413 - 424
SICI:
1075-2617(200108)7:8<413:MABAOO>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
PARA-SUBSTITUTED PHENYLALANINE; PHASE PEPTIDE-SYNTHESIS; RECEPTOR; 8-D-HOMOARGININ-VASOPRESSIN; DIASTEREOISOMERS; VASOPRESSIN; ANTAGONISTS; SEPARATION; TYROSINE; UTERUS;
Keywords:
aromatic ring; biological activity; magnesium; oxytocin analogues;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
54
Recensione:
Indirizzi per estratti:
Indirizzo: Slaninova, J Acad Sci Czech Republ, Inst Organ Chem & Biochem, Dept Peptide Biochem, Flemingovo Nam 2, CR-16610 Prague 6, Czech Republic Acad Sci Czech Republ Flemingovo Nam 2 Prague Czech Republic 6
Citazione:
J. Slaninova et al., "Magnesium and biological activity of oxytocin analogues modified on aromatic ring of amino acid in position 2", J PEPT SCI, 7(8), 2001, pp. 413-424

Abstract

For the purpose of evaluating substitution effects in the ortho, meta or para positions of the aromatic ring of tyrosine or phenylalanine in position2 of oxytocin on uterotonic activity in vitro in the presence and absence of magnesium ions, six new analogues of oxytocin ([D- and L-M-methylphenylalanine(2)] oxytocin, [D- and L-M-methoxyphenylalanine(2)] oxytocin and [D- and L-O-methyltyrosine(2)]oxytocin) were synthesized and several previouslydescribed analogues resynthesized. For the phenylalanine series, it is found that, in the absence of magnesium ions, substitution of the ortho and meta positions leads to loss of intrinsic activity (the analogues are antagonists) in contrast to the para position. In the tyrosine series, only methylsubstitution in the meta position has this effect (substitution of ortho position only attenuates the agonistic biological activity). Addition of Mg ions restores to a certain degree the agonistic activity in the case of theO-methylphenylalanine analogue and enhances the agonistic activity of O-methyltyrosine oxytocin. All other analogues keep the original qualities as in the absence of Mg. Molecular modelling calculations of the structure of the above analogues was carried out to help explain these findings of the molecular level. Copyright (C) 2001 European Peptide Society and John Wiley &Sons, Ltd.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/03/20 alle ore 11:08:03