Pharmacologic implications of α‐adrenocreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens

Peter J. Rice, Duane Miller, Theodore D. Sokoloski, Popat N. Patil

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

After alkylation of a fraction of the total α‐adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (−)‐ and (+)‐epinephrine in functional studies were 7 × 10−7 M and 2 × 10−5 M, respectively. In the adrenoreceptor‐containing tissue fraction, when 3H‐labeled WB4101 was used as the interacting ligand, for each enantiomer who affinity sites were found. Only the low‐affinity dissociation consant for each isomer correlates with the constant obtained from the functional studies. If the change in Gibb's free energy. ΔG°, is calculated from the low‐affinity binding constants, the values −8.1 and −6.2 kcal/mol for (−)‐ and (+)‐isomer, respectively, are obained. The small difference in the value between isomers forms a hydrogen bond with the receptor. The interaction of epinephrine with this receptor appears to be driven largely by the entropy of the drug‐receptor interaction with only a small nonsteroselective contribution from the enthalpy of ineraction.

Original languageEnglish (US)
Pages (from-to)14-19
Number of pages6
JournalChirality
Volume1
Issue number1
DOIs
StatePublished - Jan 1 1989

Fingerprint

Phenoxybenzamine
Vas Deferens
Enantiomers
Alkylation
Entropy
Isomers
Adrenergic Receptors
Epinephrine
Rats
Hydrogen
Ligands
Free energy
Enthalpy
Hydrogen bonds
Tissue
(2-(2',6'-dimethoxy)phenoxyethylamino)methylbenzo-1,4-dioxane

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Pharmacologic implications of α‐adrenocreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens. / Rice, Peter J.; Miller, Duane; Sokoloski, Theodore D.; Patil, Popat N.

In: Chirality, Vol. 1, No. 1, 01.01.1989, p. 14-19.

Research output: Contribution to journalArticle

Rice, Peter J. ; Miller, Duane ; Sokoloski, Theodore D. ; Patil, Popat N. / Pharmacologic implications of α‐adrenocreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens. In: Chirality. 1989 ; Vol. 1, No. 1. pp. 14-19.
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