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. 2012 Aug 23;6(1):217–235. doi: 10.1242/dmm.008243

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© 2012. Published by The Company of Biologists Ltd

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial Share Alike License (http://creativecommons.org/licenses/by-nc-sa/3.0), which permits unrestricted non-commercial use, distribution and reproduction in any medium provided that the original work is properly cited and all further distributions of the work or adaptation are subject to the same Creative Commons License terms.

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Fig. 6. — SAR analysis based on activity cliffs. (A–F) High-potency fascin-pathway modifiers (gray background) compared with structurally similar low-potency (light gray background) or inactive (white background) compounds. The highlighted substructures can be inferred to influence activity in the fascin bioassay. (A–C) Fascin-pathway enhancers (green highlights). (A) Estradiol propionate: the size of the side chain (oval) on the carboxy group on the sterol D ring is associated with activity, suggesting that in estradiol acetate the side chain is too small, whereas in estradiol valerate and cypionate, it is too large. (B) Sulfamethazine: activity is associated with dimethylation (circles) of the pyrimidine ring. Removal (asterisk) of one (sulfamerazine) or both (sulfadiazine and sulfapyridine) methyl groups is associated with loss of activity. (C) Mephenesin: replacement of the methyl group with a methoxy group in guaifenesin (circles) is associated with lack of activity. (D–F) Fascin-pathway blockers (magenta highlights). (D) Imipramine: in three other tricyclic compounds, single changes are associated with lack of activity. Desipramine is lacking a methyl group of the alkyl nitrogen (circles); clomipramine has a chloride on one of the aromatic rings (asterisks); trimipramine has a methyl substitution in the middle of the alkyl chain (arrows). (E) Suprofen: replacement of a hydrogen with a methyl group (circles) creates suprofen methyl ester, which is inactive. (F) Nifedipine: two changes, the position of the nitro group on the aromatic ring (asterisks) and addition of a methyl group (arrows), are associated with lack of activity of nitrendipine.