Syntheses and adrenergic activities of ring-fluorinated epinephrines.

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Adejare A, Gusovsky F, Padgett W, Creveling CR, Daly JW, Kirk KL

Syntheses and adrenergic activities of ring-fluorinated epinephrines.

J Med Chem. 1988 Oct;31(10):1972-7.

PubMed ID
2845082 [ View in PubMed
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Abstract

The study of chemical and biological effects of fluorine substitution on the aromatic ring of catecholamines has now been extended to epinephrine (Epi). 2- and 6-fluoroepinephrines (2-FEpi and 6-FEpi) have been synthesized. Fluorine substitution on the 2- or 6-carbon of the aromatic ring alters the selectivity of epinephrine toward alpha- and beta-adrenergic receptors, similar in manner to the change in selectivity seen with norepinephrine (NE). Thus, 2-FEpi is a relatively selective beta-adrenergic ligand, while 6-FEpi is a relatively selective alpha-adrenergic ligand. Fluorine substitution of Epi also can markedly increase potency at either alpha- or beta-adrenergic receptors.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
EpinephrineAlpha-1A adrenergic receptorKi (nM)2000N/AN/ADetails
EpinephrineAlpha-1A adrenergic receptorEC 50 (nM)400N/AN/ADetails
EpinephrineBeta-1 adrenergic receptorKi (nM)3000N/AN/ADetails
EpinephrineBeta-1 adrenergic receptorEC 50 (nM)260N/AN/ADetails
NorepinephrineAlpha-1A adrenergic receptorKi (nM)1500N/AN/ADetails
NorepinephrineBeta-1 adrenergic receptorKi (nM)400N/AN/ADetails
NorepinephrineBeta-1 adrenergic receptorEC 50 (nM)350N/AN/ADetails