Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

Cesare Giordano; Anna Sansone; Annalisa Masi; Gino Lucente; Pasqualina Punzi; Adriano Mollica; Francesco Pinnen; Federica Feliciani; Ivana Cacciatore; Peg Davis; Josephine Lai; Shou Wu Ma; Frank Porreca; Victor Hruby

doi:10.1016/j.ejmech.2010.07.022

Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

Cesare Giordano, Anna Sansone, Annalisa Masi, Gino Lucente, Pasqualina Punzi, Adriano Mollica, Francesco Pinnen, Federica Feliciani, Ivana Cacciatore, Peg Davis, Josephine Lai, Shou Wu Ma, Frank Porreca, Victor Hruby

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH₂; EM1 and Tyr-Pro-Phe-Phe-NH₂; EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH ₂) exhibit an extremely high selectivity for μ-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of β-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3- pyrrolidinesulphonic acid (βPrs) have been synthesized and their binding affinity and functional activity have been investigated. The highest μ-receptor affinity is shown by [(S)βPrs²]EM2 analogue (6e) which represents the first example of a β-sulphonamido analogue in the field of opioid peptides.

Original language	English (US)
Pages (from-to)	4594-4600
Number of pages	7
Journal	European journal of medicinal chemistry
Volume	45
Issue number	10
DOIs	https://doi.org/10.1016/j.ejmech.2010.07.022
State	Published - Oct 2010

Keywords

Endomorphins
Opioid peptides
Peptide synthesis
Unusual amino acids
β-Sulphonamido peptides

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2010.07.022

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Giordano, C., Sansone, A., Masi, A., Lucente, G., Punzi, P., Mollica, A., Pinnen, F., Feliciani, F., Cacciatore, I., Davis, P., Lai, J., Ma, S. W., Porreca, F., & Hruby, V. (2010). Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2. European journal of medicinal chemistry, 45(10), 4594-4600. https://doi.org/10.1016/j.ejmech.2010.07.022

Giordano, C, Sansone, A, Masi, A, Lucente, G, Punzi, P, Mollica, A, Pinnen, F, Feliciani, F, Cacciatore, I, Davis, P, Lai, J, Ma, SW, Porreca, F & Hruby, V 2010, 'Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2', European journal of medicinal chemistry, vol. 45, no. 10, pp. 4594-4600. https://doi.org/10.1016/j.ejmech.2010.07.022

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abstract = "The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH2; EM1 and Tyr-Pro-Phe-Phe-NH2; EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH 2) exhibit an extremely high selectivity for μ-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of β-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3- pyrrolidinesulphonic acid (βPrs) have been synthesized and their binding affinity and functional activity have been investigated. The highest μ-receptor affinity is shown by [(S)βPrs2]EM2 analogue (6e) which represents the first example of a β-sulphonamido analogue in the field of opioid peptides.",

keywords = "Endomorphins, Opioid peptides, Peptide synthesis, Unusual amino acids, β-Sulphonamido peptides",

author = "Cesare Giordano and Anna Sansone and Annalisa Masi and Gino Lucente and Pasqualina Punzi and Adriano Mollica and Francesco Pinnen and Federica Feliciani and Ivana Cacciatore and Peg Davis and Josephine Lai and Ma, {Shou Wu} and Frank Porreca and Victor Hruby",

note = "Funding Information: This research was supported in part by grants from the U.S. Public Health Service , National Institutes of Health , DR 06784 and DA 13449 (VJH) .",

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doi = "10.1016/j.ejmech.2010.07.022",

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T1 - Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

AU - Giordano, Cesare

AU - Sansone, Anna

AU - Masi, Annalisa

AU - Lucente, Gino

AU - Punzi, Pasqualina

AU - Mollica, Adriano

AU - Pinnen, Francesco

AU - Feliciani, Federica

AU - Cacciatore, Ivana

AU - Davis, Peg

AU - Lai, Josephine

AU - Ma, Shou Wu

AU - Porreca, Frank

AU - Hruby, Victor

N1 - Funding Information: This research was supported in part by grants from the U.S. Public Health Service , National Institutes of Health , DR 06784 and DA 13449 (VJH) .

PY - 2010/10

Y1 - 2010/10

N2 - The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH2; EM1 and Tyr-Pro-Phe-Phe-NH2; EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH 2) exhibit an extremely high selectivity for μ-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of β-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3- pyrrolidinesulphonic acid (βPrs) have been synthesized and their binding affinity and functional activity have been investigated. The highest μ-receptor affinity is shown by [(S)βPrs2]EM2 analogue (6e) which represents the first example of a β-sulphonamido analogue in the field of opioid peptides.

AB - The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH2; EM1 and Tyr-Pro-Phe-Phe-NH2; EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH 2) exhibit an extremely high selectivity for μ-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of β-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3- pyrrolidinesulphonic acid (βPrs) have been synthesized and their binding affinity and functional activity have been investigated. The highest μ-receptor affinity is shown by [(S)βPrs2]EM2 analogue (6e) which represents the first example of a β-sulphonamido analogue in the field of opioid peptides.

KW - Endomorphins

KW - Opioid peptides

KW - Peptide synthesis

KW - Unusual amino acids

KW - β-Sulphonamido peptides

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Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

Abstract

Keywords

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