2012
DOI: 10.1016/j.ejmech.2012.10.041
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Probes for narcotic receptor mediated phenomena. 46. N-substituted-2,3,4,9,10,10a-hexahydro-1H-1,4a-(epiminoethano)phenanthren-6- and 8-ols – Carbocyclic relatives of f-oxide-bridged phenylmorphans

Abstract: Oxide-bridged phenylmorphans were conceptualized as topologically distinct, structurally rigid ligands with 3-dimensional shapes that could not be appreciably modified on interaction with opioid receptors. An enantiomer of the N-phenethyl-substituted ortho-f isomer was found to have high affinity for the μ-receptor (Ki = 7 nM) and was about four times more potent than naloxone as an antagonist. In order to examine the effect of introduction of a small amount of flexibility into these molecules, we have replace… Show more

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Cited by 6 publications
(10 citation statements)
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“…As noted formerly,[15, 16] [ 3 H][D-Ala2-MePhe4,Gly-ol5]enkephalin ([ 3 H]DAMGO, SA=44-48 Ci/mmol) was used to label MOR, [ 3 H][D-Ala2,D-Leu5]enkephalin ([ 3 H]DADLE, SA=40-50 Ci/mmol) to label DOR and [ 3 H](-)-U69,593 (SA=50 Ci/mmol) to label KOR binding sites. On the day of the assay, cell pellets were thawed on ice for 15 min then homogenized with a polytron in 10 mL/pellet of ice-cold 10 mM Tris-HCl, pH 7.4.…”
Section: Methodsmentioning
confidence: 58%
See 3 more Smart Citations
“…As noted formerly,[15, 16] [ 3 H][D-Ala2-MePhe4,Gly-ol5]enkephalin ([ 3 H]DAMGO, SA=44-48 Ci/mmol) was used to label MOR, [ 3 H][D-Ala2,D-Leu5]enkephalin ([ 3 H]DADLE, SA=40-50 Ci/mmol) to label DOR and [ 3 H](-)-U69,593 (SA=50 Ci/mmol) to label KOR binding sites. On the day of the assay, cell pellets were thawed on ice for 15 min then homogenized with a polytron in 10 mL/pellet of ice-cold 10 mM Tris-HCl, pH 7.4.…”
Section: Methodsmentioning
confidence: 58%
“…As previously described,[14, 15] the recombinant CHO cells (hMOR-CHO, hDOR-CHO and hKORCHO) were produced by stable transfection with the respective human opioid receptor cDNA, and provided by Dr. Larry Toll (SRI International, CA). The cells were grown in plastic flasks in DMEM (90%) (hDOR-CHO and hKOR-CHO) or DMEM/ F-12 (45%/ 45%) medium (hMOR-CHO) containing 5% FBS (Invitrogen), 5% FetalClone II (HyClone), and Geneticin (G-418: 0.10-0.2 mg/ml) (Invitrogen) under 95% air/5% CO 2 at 37° C. Cell monolayers were harvested and frozen in - 80 °C.…”
Section: Methodsmentioning
confidence: 99%
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“…Catalytic hydrogenation of the mixture of compounds 10 and 11 gave 4,5-epoxy ring-opened by-products. All other attempts (dissolving metal, 21 [(Ph 3 P)CuH] 6 22 with or without Et 3 SiH, DIBAL + CuMe, 23 and transfer hydrogenation 24 ) to reduce the double bond were unsuccessful.…”
Section: Resultsmentioning
confidence: 99%