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Structure and biological activity of (-)-[3H]dihydroalprenolol, a radioligand for studies of beta-adrenergic receptors.

Publication ,  Journal Article
Randall, MH; Altman, LJ; Lefkowitz, RJ
Published in: J Med Chem
August 1977

(-)-Alprenolol is a potent competitive beta-adrenergic antagonist. "(-)-[3H]Alprenolol", a radioactive form of this agent produced by catalytic reduction with tritium, has recently been used successfully as a radioligand for direct studies of beta-adrenergic receptors. In this communication it is documented that the compound formed by catalytic reduction of (-)-alprenolol with tritium gas is the saturated product (-)-[3H]dihydroalprenolol in which tritium is added across the double bond and exchanged into the adjacent benzylic position. No exchange into the aromatic ring was observed. These conclusions were substantiated by results obtained on hydrogenation and deuteration of (-)-alprenolol. The biological activity of (-)-[3H]dihydroalprenolol, dihydroalprenolol, and alprenolol was also shown to be identical as assessed by direct ligand binding and inhibition of catecholamine-stimulated adenylate cyclase.

Duke Scholars

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

August 1977

Volume

20

Issue

8

Start / End Page

1090 / 1094

Location

United States

Related Subject Headings

  • Tritium
  • Structure-Activity Relationship
  • Receptors, Adrenergic, beta
  • Receptors, Adrenergic
  • Medicinal & Biomolecular Chemistry
  • Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Ligands
  • In Vitro Techniques
  • Hydrogenation
 

Citation

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Randall, M. H., Altman, L. J., & Lefkowitz, R. J. (1977). Structure and biological activity of (-)-[3H]dihydroalprenolol, a radioligand for studies of beta-adrenergic receptors. J Med Chem, 20(8), 1090–1094. https://doi.org/10.1021/jm00218a020
Randall, M. H., L. J. Altman, and R. J. Lefkowitz. “Structure and biological activity of (-)-[3H]dihydroalprenolol, a radioligand for studies of beta-adrenergic receptors.J Med Chem 20, no. 8 (August 1977): 1090–94. https://doi.org/10.1021/jm00218a020.
Randall, M. H., et al. “Structure and biological activity of (-)-[3H]dihydroalprenolol, a radioligand for studies of beta-adrenergic receptors.J Med Chem, vol. 20, no. 8, Aug. 1977, pp. 1090–94. Pubmed, doi:10.1021/jm00218a020.
Journal cover image

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

August 1977

Volume

20

Issue

8

Start / End Page

1090 / 1094

Location

United States

Related Subject Headings

  • Tritium
  • Structure-Activity Relationship
  • Receptors, Adrenergic, beta
  • Receptors, Adrenergic
  • Medicinal & Biomolecular Chemistry
  • Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Ligands
  • In Vitro Techniques
  • Hydrogenation