1995
DOI: 10.1021/bc00033a004
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"Cleavable Trifunctional" Approach to Receptor Affinity Labeling: Regeneration of Binding to A1-Adenosine Receptors

Abstract: A general approach for reversible affinity labeling of receptors has been developed. The objective is to carry out a series of chemical modifications resulting in a covalently-modified, yet functionally-regenerated, receptor protein that also may contain a reporter group. The ligand recognition site of A1-adenosine receptors in bovine brain membranes was probed to demonstrated the feasibility of this approach. Use of disulfide or ester linkages, intended for cleavage by exposure of the labeled receptor to eith… Show more

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Cited by 24 publications
(21 citation statements)
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“…The aqueous solution was basified (pH = 9) with 1 M NaOH and extracted twice with EtOAc. The combined EtOAc phases were washed twice with water, dried (Na 2 SO 4 ) and evaporated in vacuo to yield 4.10 g (16.2 mmol, 45% ) of 3 as a white solid: R f = 0.47 (CHCl 3 /MeOH 9:1, 1% concentrated NH 4 OH); NMR spectra matching literature data [54]. …”
Section: Methodsmentioning
confidence: 76%
“…The aqueous solution was basified (pH = 9) with 1 M NaOH and extracted twice with EtOAc. The combined EtOAc phases were washed twice with water, dried (Na 2 SO 4 ) and evaporated in vacuo to yield 4.10 g (16.2 mmol, 45% ) of 3 as a white solid: R f = 0.47 (CHCl 3 /MeOH 9:1, 1% concentrated NH 4 OH); NMR spectra matching literature data [54]. …”
Section: Methodsmentioning
confidence: 76%
“…Reporter groups, such as fluorescent dyes and a spin label, were included as substituents in the third position of irreversibly binding analogues, which were designed for spectroscopic assays, histochemical characterization, and biochemical characterization of the receptor protein. We also designed and synthesized trifunctional ligands for the A 1 AR that contain a cleavable disulfide linkage in the chain, for chemically induced regeneration of the receptor-binding site for the purine by reduction of the disulfide [82]. …”
Section: Irreversibly Binding Ar Ligands For Receptor Inactivation Anmentioning
confidence: 99%
“…[28] The second step, the DCC condensation of Cyst-mBoc with the carboxyl groups of P(VP-co-VP-COOH) (Scheme 2b), led to P(VP-co-VP-Cyst-mBoc) containing 15% of disulfide groups on a molar basis.…”
Section: Resultsmentioning
confidence: 99%
“…N-tert-Butyloxycarbonyl Cystamine [28] (Cyst-mBoc . * HCl) TEA (2.696 g, 26.65 mmol) was added to a dry methanol solution (100 ml) of cystamine bis-hydrochloride (2.00 g, 8.88 mmol), and the solution stirred for 15 min at room temperature.…”
Section: Methodsmentioning
confidence: 99%