Newendomorphin-2(EM-2)analoguesincorporating(Z)-R,β-didehydrophenylalanine(Δ Phe)in placeofthenativephenylalanineinEM-2arereported.Tyr-Pro-ΔZPhe-Phe-NH2 {[ΔZPhe 3 ]EM-2}(1), Tyr-Pro-Phe-ΔZ Phe-NH2 {[ΔZ Phe 4 ]EM-2}(2),andTyr-Pro-ΔZ Phe-ΔZ Phe-NH2 {[ΔZ Phe 3,4 ]EM-2}(3) havebeensynthesized,theiropioidreceptorbindingaffinitiesandtissuebioassayactivitieswere determined,andtheirconformationalpropertieswereexamined.Compound 2 showshigh μ opioid receptorselectivityand μ agonistactivitycomparabletothoseofthenativepeptide.Theconformation adoptedinsolutionandinthecrystalby N-Boc-Tyr-Pro-ΔZPhe-Phe-NH2 (8)isreported.

Synthesis and evaluation of new endomorphin-2 analogues containing (Z)-α,β-didehydrophenylalanine (δZPhe) residues

MOLLICA, ADRIANO;PINNEN, Francesco Enrico;FELICIANI, FEDERICA;
2010-01-01

Abstract

Newendomorphin-2(EM-2)analoguesincorporating(Z)-R,β-didehydrophenylalanine(Δ Phe)in placeofthenativephenylalanineinEM-2arereported.Tyr-Pro-ΔZPhe-Phe-NH2 {[ΔZPhe 3 ]EM-2}(1), Tyr-Pro-Phe-ΔZ Phe-NH2 {[ΔZ Phe 4 ]EM-2}(2),andTyr-Pro-ΔZ Phe-ΔZ Phe-NH2 {[ΔZ Phe 3,4 ]EM-2}(3) havebeensynthesized,theiropioidreceptorbindingaffinitiesandtissuebioassayactivitieswere determined,andtheirconformationalpropertieswereexamined.Compound 2 showshigh μ opioid receptorselectivityand μ agonistactivitycomparabletothoseofthenativepeptide.Theconformation adoptedinsolutionandinthecrystalby N-Boc-Tyr-Pro-ΔZPhe-Phe-NH2 (8)isreported.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11564/177594
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 36
  • ???jsp.display-item.citation.isi??? 30
social impact