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. Author manuscript; available in PMC: 2008 Dec 27.
Published in final edited form as: J Med Chem. 2007 Dec 4;50(26):6673–6684. doi: 10.1021/jm070685e

Table 1.

Binding affinities of new biphenylthiols for monoamine transporters*

graphic file with name nihms62855f6.jpg
Ki (nM)
Compound R1 R2 SERT NET DAT
28 H O(CH2)2F 0.25 ± 0.02 7.5 ± 0.7 340 ± 64
29 F O(CH2)2F 0.10 ± 0.01 37 ± 5 >1000
30 Cl O(CH2)2F 0.03 ± 0.001 97 ± 3 847 ± 73
31 Br O(CH2)2F 0.05 ± 0.01 114 ± 8 >1000
40 H O(CH2)3F 1.4 ± 0.2 12 ± 2 299 ± 9
41 F O(CH2)3F 0.95 ± 0.13 95 ± 9 >1000
42 Br O(CH2)3F 0.15 ± 0.02 >1000 >1000
47 H O(CH2)2OH 1.1 ± 0.04 11 ± 1 351 ± 49
48 F O(CH2)2OH 1.2 ± 0.1 56 ± 5 >1000
49 H O(CH2)3OH 1.3 ± 0.3 7 ± 0.2 443 ± 68
50 Br O(CH2)3OH 0.21 ± 0.02 279 ± 25 >1000
43 H OCH3 5 ± 0.4 14 ± 1 576 ± 31
44 H OH 17 ± 2 33 ± 3 659 ± 38
*

In vitro binding assays (n = 3) were employed to determine inhibition constants (Ki ± SEM) with membrane preparations of three different groups of LLC-PK1 cells, each expressing one specific monoamine transporter, either SERT, DAT or NET.47