Exploration of Universal Cysteines in the Binding Sites of Three Opioid Receptor Subtypes by Disulfide-Bonding Affinity Labeling with Chemically Activated Thiol-Containing Dynorphin A Analogs.

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概要

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• A ligand containing an SNpys group, i.e. 3-nitro-2-pyridinesulfenyl linked to a mercapto (or thiol) group, can bind covalently to a free mercapto group to form a disulfide bond via the thiol-disulfide exchange reaction. This SNpys chemistry has been successfully applied to the discriminative affinity labeling of μ and δ opioid receptors with SNpys-containing enkephalins [Yasunaga, T. et al. (1996) J. Biochem. 120, 459-465]. In order to explore the mercapto groups conserved at or near the ligand binding sites of three opioid receptor subtypes, we synthesized two Cys (Npys)-containing analogs of dynorphin A, namely, [D-Ala2, Cys (Npys)8] dynorphin A-(1-9) amide (1) and [D-Ala2, Cys (Npys)12] dynorphin A-(1-13) amide (2). When rat (μ and δ) or guinea pig (κ) brain membranes were incubated with these Cys (Npys)-containing dynorphin A analogs and then assayed for inhibition of the binding of DAGO (μ), deltorphin II (δ), and U-69593 (δ), the number of receptors decreased sharply, depending upon the concentrations of these Cys (Npys)-containing dynorphin A analogs. It was found that dynorphin A analogs 1 and 2 effectively label μ receptors (EC50)=27-33 nM), but also label δ receptors fairly well (160-180 nM). However, for δ receptors they showed drastically different potencies as to affinity labeling; i.e., EC50=210 nM for analog 1, but 10, 000 nM for analog 2. Analog 2 labeled κ receptors about 50 times more weakly than analog 1. These results suggested that dynorphin A analog 1 labels the Cys residues conserved in μ, δ, and κ receptors, whereas analog 2 only labels the Cys residues conserved in μ and δ receptors.

• 社団法人 日本生化学会の論文

著者

• Shirasu Naoto

  Laboratory Of Structure-function Biochemistry Department Of Chemistry Faculty And Graduate School Of

• Shimohigashi Yasuyuki

  Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University

• Nose Takeru

  Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University

• Nakao Hidenori

  Laboratory Of Structure-function Biochemistry Department Of Molecular Chemistry Graduate School Of S

• Kuromizu Takuya

  Laboratory Of Structure-function Biochemistry Department Of Molecular Chemistry Graduate School Of S

• Chuman Yoshiro

  Laboratory Of Biological Chemistry Department Of Chemistry Faculty Of Science Hokkaido University

• Nose Takeru

  Laboratory of Structure-Function Biochemistry, Department Molecular Chemistry, Graduate School of Science, Kyushu University

• Costa Tommaso

  Laboratori di Farmacologia, Istituto Spuperiore di Santiá

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