Abstract
A new series of fentanyl derivatives [i.e., N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinoalkyl)propanamide] bearing aliphatic alkaneguanidinium moieties were prepared. Their affinities for the micro opioid receptors and for the I(2)-imidazoline binding sites (I(2)-IBS) were determined on human post-mortem prefrontal cortex membranes. All of these hybrid compounds had significant and/or very high affinity for both receptors in the nanomolar range, meaning an improvement compared to the prototype N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinopropyl)propanamide previously reported.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkanes / chemistry
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Alkanes / metabolism*
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Animals
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Binding Sites / physiology
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Fentanyl / chemistry
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Fentanyl / metabolism*
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Guanidines / metabolism*
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Imidazoline Receptors
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Mice
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Piperazines / metabolism*
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Protein Binding / physiology
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Receptors, Drug / metabolism*
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Receptors, Opioid, mu / metabolism*
Substances
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3-(4-guanidinophenyl)-N-(2-phenylethyl)-3-((4-(3,3-diphenylpropylaminocarbonyl)piperazin-1-yl)carbonyl)propanamide
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Alkanes
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Guanidines
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Imidazoline Receptors
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Piperazines
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Receptors, Drug
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Receptors, Opioid, mu
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Fentanyl