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. Author manuscript; available in PMC: 2018 Nov 16.
Published in final edited form as: Cell. 2017 Nov 16;171(5):1165–1175.e13. doi: 10.1016/j.cell.2017.10.035

Table 1. Structural features influencing GTPγS binding and βarrestin2 recruitment.

Potency (EC50) and efficacy (EMAX, percent of DAMGO) values from GTPγS binding assays performed on CHO-hMOR membranes and βarrestin2 recruitment determined by EFC βarrestin2 assay with the U2OS-βarrestin2-hMOR-PathHunter cells. Data are presented as mean ± S.E.M. of 3 or more assays run in duplicate or triplicate. See also: Figure S1 for chemical synthesis; Figure S2 for counter-screens against other opioid receptors; and Table S1 for binding affinities for the compounds below the dotted line.
Agonist Entry Substituentsa GTPγS binding βarrestin2 recruitment
R1 R2 R3 R4 EC50 nM EMAX % EC50 nM EMAX %
graphic file with name nihms917454t1.jpg DAMGO 33 ± 1.4 100 229 ± 12 100
Morphine 64 ± 4.2 81 ± 1 372 ± 20 24 ± 1
Sufentanil 1.3 ± 0.18 78 ± 1 1.5±0.6 73±11
Fentanyl 43 ± 9.7 80 ± 5 53 ± 6.8 60 ± 2
(±) SR-8595 1 H H H Me 102 ± 10 89 ± 7 447 ± 52 67 ± 3.8
(±) SR-11065 2 H H Cl Me 16 ± 1.2 97 ± 7 253 ± 88 76 ± 8.8
SR-20382 3 H H Cl H 563 ± 104 62 ± 4 7656 ± 1469 67 ± 9.8
SR-20437 4 Cl Cl H H 171 ± 24 60 ± 5 1092 ± 273 24 ± 3.6
SR-17018 5 Cl Cl Cl H 97 ± 13 75 ± 4 >10,000 10 ± 6c
SR-15099 6 Cl Cl Br H 155 ± 11 81 ± 4 >10,000 3 ± 1c
(±) SR-14968 7 Cl Cl Br Me 8.9 ± 3.8 92 ± 1 2438 ± 710 64 ± 5
(±) SR-14969a 8 Cl Cl Cl Me 28 ± 7.7 88 ± 2 2949 ± 789 81 ± 6
SR-15098a 9 Cl Cl Cl H 179 ± 24 68 ± 4 >10,000 12 ± 5c
(±) SR-11501 10 H H b Me 106 ± 9.1 70 ± 1 374 ± 60 59 ± 2
a

R5 = F;

b

(R3 + R4) = (-OCH2CH2O-); for all other compounds, R4 = R5 = H;

c

percent of maximum stimulation at the 10 μM concentration is presented rather than EMAX.