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. Author manuscript; available in PMC: 2010 Jan 7.
Published in final edited form as: Bioorg Med Chem Lett. 2008 Dec 29;19(6):1825–1829. doi: 10.1016/j.bmcl.2008.12.093

Table 1.

Binding affinity and functional assay results for the 14-O-substituted naltrexone derivatives

Compound Ki ± SEM (nM)
Selectivity
Percent Max of DAMGO
[3H]DAMGO (μ) [3H] NTI (δ) [3H] norBNI (κ) δ/μ κ/μ
Naltrexone 0.26 ± 0.02 117.00 ± 8.90 5.15 ± 0.26 450 20 0.00
β-FNA 0.41 ± 0.04 27.78 ± 4.60 0.94 ± 0.05 68 2 0.00
CTAP 2.02 ± 0.71 1441.00 ± 106.10 1012.70 ± 174.80 713 501 0.00
1 0.14 ± 0.03 117.38 ± 17.97 25.50 ± 6.50 838 182 0.00
2 1.59 ± 0.61 170.30 ± 12.64 47.81 ± 8.48 107 30 0.00
3 5.58 ± 1.34 405.32 ± 234.68 49.21 ± 20.37 73 9 0.00
4 123.23 ± 38.23 >10,000.00 586.42 ± 32.39 >81 5 0.00
5 68.40 ± 6.04 >10,000.00 >10,000.00 >146 >146 0.00
6 1.44 ± 0.32 22.81 ± 19.52 67.15 ± 36.72 16 47 0.00
7 2.69 ± 0.72 818.43 ± 507.23 148.23 ± 55.53 304 55 22.00 ± 10.30
8 225.27 ± 46.6 907.18 ± 192.99 46.57 ± 13.53 4 <1 0.00

The Ki values for the mu, delta and kappa opioid receptors were n = 3. The averages were reported along with their standard error of the means, SEM, for each compound. The comparison to percent stimulation of DAMGO was the Emax of the compound compared to the Emax of DAMGO (normalized to 100%). The DAMGO EC50 value was 45.1 ± 6.63 nM and its Emax value was 366 ± 23% stimulation over basal using a [35S]GTPγS functional assay. Naltrexone, β-FNA and CTAP were tested along as positive controls under the same conditions.