Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for mu-opioid receptors and I2-imidazoline binding sites.

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Dardonville C, Jagerovic N, Callado LF, Meana JJ

Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for mu-opioid receptors and I2-imidazoline binding sites.

Bioorg Med Chem Lett. 2004 Jan 19;14(2):491-3.

PubMed ID

14698188 [ View in PubMed

]

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.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Fentanyl	Mu-type opioid receptor	Ki (nM)	2.9	N/A	N/A	Details