The crystal structure of a bimorphinan with highly selective kappa opioid receptor antagonist activity

Zofia Urbańczyk-Lipkowska; Margaret C. Etter; Andrzej W. Lipkowski; Philip S. Portoghese

doi:10.1016/0022-2860(87)80047-9

The crystal structure of a bimorphinan with highly selective kappa opioid receptor antagonist activity

Zofia Urbańczyk-Lipkowska, Margaret C. Etter, Andrzej W. Lipkowski, Philip S. Portoghese

Medicinal Chemistry

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

16 Scopus citations

Abstract

The crystal structure of the dihydrobromide heptahydrate of nor-binaltorphimine (17, 17′-bis(cyclopropylmethyl)-6,6′,7,7′-tetrahydro-4,5α: 4′,5′α-diepoxy-6,6′-imino[7,7′ bimorphinan]-3,3′,14,14′-tetraol)is presented. This structure is the first reported structure of a rigid bivalent opioid ligand. Two morphinan pharmacophores are connected by a rigid spacer, the pyrrole ring. The nor-binaltorphimine structure itself shows unique, high selectivity as a kappa opioid receptor antagonist. Crystal data: P3₂, Z = 3, a = b = 20.223 (4), c = 9.541(7) Å, α = β = 90°, γ = 120°; R = 0.079 (1765 reflections, F_obs > 1σ(F)).

Original language	English (US)
Pages (from-to)	287-295
Number of pages	9
Journal	Journal of Molecular Structure
Volume	159
Issue number	3-4
DOIs	https://doi.org/10.1016/0022-2860(87)80047-9
State	Published - Jul 1987

Bibliographical note

Funding Information:
This research was partially supported by the National Institute on Drug Abuse (DA 02659) to PSP. Helpful discussionsw ith Professor Doyle Britton, University of Minnesota, about crystallographic aspects of this work are greatly appreciated.

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title = "The crystal structure of a bimorphinan with highly selective kappa opioid receptor antagonist activity",

abstract = "The crystal structure of the dihydrobromide heptahydrate of nor-binaltorphimine (17, 17′-bis(cyclopropylmethyl)-6,6′,7,7′-tetrahydro-4,5α: 4′,5′α-diepoxy-6,6′-imino[7,7′ bimorphinan]-3,3′,14,14′-tetraol)is presented. This structure is the first reported structure of a rigid bivalent opioid ligand. Two morphinan pharmacophores are connected by a rigid spacer, the pyrrole ring. The nor-binaltorphimine structure itself shows unique, high selectivity as a kappa opioid receptor antagonist. Crystal data: P32, Z = 3, a = b = 20.223 (4), c = 9.541(7) {\AA}, α = β = 90°, γ = 120°; R = 0.079 (1765 reflections, Fobs > 1σ(F)).",

author = "Zofia Urba{\'n}czyk-Lipkowska and Etter, {Margaret C.} and Lipkowski, {Andrzej W.} and Portoghese, {Philip S.}",

note = "Funding Information: This research was partially supported by the National Institute on Drug Abuse (DA 02659) to PSP. Helpful discussionsw ith Professor Doyle Britton, University of Minnesota, about crystallographic aspects of this work are greatly appreciated.",

year = "1987",

month = jul,

doi = "10.1016/0022-2860(87)80047-9",

language = "English (US)",

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journal = "Journal of Molecular Structure",

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T1 - The crystal structure of a bimorphinan with highly selective kappa opioid receptor antagonist activity

AU - Urbańczyk-Lipkowska, Zofia

AU - Etter, Margaret C.

AU - Lipkowski, Andrzej W.

AU - Portoghese, Philip S.

N1 - Funding Information: This research was partially supported by the National Institute on Drug Abuse (DA 02659) to PSP. Helpful discussionsw ith Professor Doyle Britton, University of Minnesota, about crystallographic aspects of this work are greatly appreciated.

PY - 1987/7

Y1 - 1987/7

N2 - The crystal structure of the dihydrobromide heptahydrate of nor-binaltorphimine (17, 17′-bis(cyclopropylmethyl)-6,6′,7,7′-tetrahydro-4,5α: 4′,5′α-diepoxy-6,6′-imino[7,7′ bimorphinan]-3,3′,14,14′-tetraol)is presented. This structure is the first reported structure of a rigid bivalent opioid ligand. Two morphinan pharmacophores are connected by a rigid spacer, the pyrrole ring. The nor-binaltorphimine structure itself shows unique, high selectivity as a kappa opioid receptor antagonist. Crystal data: P32, Z = 3, a = b = 20.223 (4), c = 9.541(7) Å, α = β = 90°, γ = 120°; R = 0.079 (1765 reflections, Fobs > 1σ(F)).

AB - The crystal structure of the dihydrobromide heptahydrate of nor-binaltorphimine (17, 17′-bis(cyclopropylmethyl)-6,6′,7,7′-tetrahydro-4,5α: 4′,5′α-diepoxy-6,6′-imino[7,7′ bimorphinan]-3,3′,14,14′-tetraol)is presented. This structure is the first reported structure of a rigid bivalent opioid ligand. Two morphinan pharmacophores are connected by a rigid spacer, the pyrrole ring. The nor-binaltorphimine structure itself shows unique, high selectivity as a kappa opioid receptor antagonist. Crystal data: P32, Z = 3, a = b = 20.223 (4), c = 9.541(7) Å, α = β = 90°, γ = 120°; R = 0.079 (1765 reflections, Fobs > 1σ(F)).

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DO - 10.1016/0022-2860(87)80047-9

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JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

IS - 3-4

ER -

The crystal structure of a bimorphinan with highly selective kappa opioid receptor antagonist activity

Abstract

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