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. Author manuscript; available in PMC: 2009 Mar 15.
Published in final edited form as: Bioorg Med Chem. 2007 Dec 23;16(6):3032–3038. doi: 10.1016/j.bmc.2007.12.032

Table 1.

Receptor Binding Affinities and Functional Bioactivities of Compounds 1–6.

graphic file with name nihms45436t1.jpg
Receptor affinity a (nM) Selectivity Functional bioactivity (nM)
Comp. Structure R Kiδ Kiμ Kiμ/Kiδ MVD (IC50)b MVD (p A2)c GPI (IC50)b
Ref. H-Dmt-Tic-NH-CH2-Bid graphic file with name nihms45436t2.jpg 0.035d 0.50d 14d 0.94±0.21 35.5±7.3
1 H-Dmt-Tic-NH-CH2-Boa graphic file with name nihms45436t3.jpg 0.283±0.048 (3) 1.42±0.25 (6) 5.0 9.42 169.9±32.2
2 H-Dmt-Tic-NH-CH2-Bta graphic file with name nihms45436t4.jpg 0.145±0.018 (3) 1.06±0.11 (4) 7.3 9.37 129.1±21.5
3 H-Dmt-Tic-NH-CH2-Indl graphic file with name nihms45436t5.jpg 0.066±0.013 (3) 0.7±0.18 (4) 10.6 9.45 208.9±48.1
4 H-Dmt-Tic-NH-CH2-Indn graphic file with name nihms45436t6.jpg 0.199±0.032 (3) 0.16±0.019 (4) 1.2# 129.0±23.9 28.41±1.74
5 H-Dmt-Tic-NH-CH2-ImidPh graphic file with name nihms45436t7.jpg 0.443±0.13 (3) 6.74±0.98 (5) 15 9.40 153.5±10.4
6 H-Dmt-Tic-NH-CH2-Imid graphic file with name nihms45436t8.jpg 0.114±0.017 (4) 1.18±0.12 (6) 10 3.63±0.52 111.3±37.8
#

μ selectivity Kiδ/ Kiμ.

a

The Ki values (nM) were determined according to Cheng and Prusoff.20 The mean ± SE with n repetitions in parenthesis is based on independent duplicate binding assays with five to eight peptide doses using several different synaptosomal preparations.

b

Agonist activity was expressed as IC50 obtained from dose-response curves. These values represents the mean ± SE for at least four tissue samples. DPDPE and PL-017 were the internal standards for MVD (δ-opioid receptor bioactivity) and GPI (μ-opioid receptor bioactivity) tissue preparation, respectively.

c

The pA2 values of opioid antagonists against the agonists (deltorphin II and endomorphin-2) were determined by the method of Kosterlitz and Watt.21

d

Data taken from Balboni et al.4