A novel N-terminal cyclic dynorphin A analogue cycloN,5[Trp3,Trp4,Glu5] dynorphin A-(1-11)NH2 that lacks the basic N-terminus

Balvinder S. Vig; Thomas F. Murray; Jane V. Aldrich

doi:10.1021/jm0256023

A novel N-terminal cyclic dynorphin A analogue cyclo^N,5[Trp³,Trp⁴,Glu⁵] dynorphin A-(1-11)NH₂ that lacks the basic N-terminus

Balvinder S. Vig, Thomas F. Murray, Jane V. Aldrich

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

32 Scopus citations

Abstract

A novel N-terminal-to-side chain cyclic dynorphin A analogue lacking the basic N-terminus was designed based on Ac[Lys²,Trp³,Trp⁴,D-Ala⁸] dynorphin A-(1-11)NH₂ (Wan et al. J. Med. Chem. 1999, 42, 3011-3013). cyclo^N,5- [Trp³,Trp⁴, Glu⁵]dynorphin A-(1-11)NH₂ showed similar κ opioid receptor affinity (K_i = 27 nM) and selectivity (K_i ratio (κ/μ/δ) = 1/12/330) to the linear peptide and antagonized dynorphin A-(1-13)NH₂ at κ opioid receptors. This is the first opioid peptide cyclized through the N-terminus that retains high opioid receptor affinity.

Original language	English (US)
Pages (from-to)	1279-1282
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	46
Issue number	8
DOIs	https://doi.org/10.1021/jm0256023
State	Published - Apr 10 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Molecular Medicine
Drug Discovery

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title = "A novel N-terminal cyclic dynorphin A analogue cycloN,5[Trp3,Trp4,Glu5] dynorphin A-(1-11)NH2 that lacks the basic N-terminus",

abstract = "A novel N-terminal-to-side chain cyclic dynorphin A analogue lacking the basic N-terminus was designed based on Ac[Lys2,Trp3,Trp4,D-Ala8] dynorphin A-(1-11)NH2 (Wan et al. J. Med. Chem. 1999, 42, 3011-3013). cycloN,5- [Trp3,Trp4, Glu5]dynorphin A-(1-11)NH2 showed similar κ opioid receptor affinity (Ki = 27 nM) and selectivity (Ki ratio (κ/μ/δ) = 1/12/330) to the linear peptide and antagonized dynorphin A-(1-13)NH2 at κ opioid receptors. This is the first opioid peptide cyclized through the N-terminus that retains high opioid receptor affinity.",

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AU - Murray, Thomas F.

AU - Aldrich, Jane V.

PY - 2003/4/10

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AB - A novel N-terminal-to-side chain cyclic dynorphin A analogue lacking the basic N-terminus was designed based on Ac[Lys2,Trp3,Trp4,D-Ala8] dynorphin A-(1-11)NH2 (Wan et al. J. Med. Chem. 1999, 42, 3011-3013). cycloN,5- [Trp3,Trp4, Glu5]dynorphin A-(1-11)NH2 showed similar κ opioid receptor affinity (Ki = 27 nM) and selectivity (Ki ratio (κ/μ/δ) = 1/12/330) to the linear peptide and antagonized dynorphin A-(1-13)NH2 at κ opioid receptors. This is the first opioid peptide cyclized through the N-terminus that retains high opioid receptor affinity.

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A novel N-terminal cyclic dynorphin A analogue cyclo^N,5[Trp³,Trp⁴,Glu⁵] dynorphin A-(1-11)NH₂ that lacks the basic N-terminus

Abstract

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