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. Author manuscript; available in PMC: 2020 Jan 1.
Published in final edited form as: Ann N Y Acad Sci. 2018 Feb 15;1435(1):18–38. doi: 10.1111/nyas.13598

Figure 6.

Figure 6

Appending a sterically-unencumbered amine on relatively flat and rigid antibiotics can enhance their activity against Gram-negative bacteria. (A) Seven examples75, 128, 132-136, 151 of conversions of Gram-positive-only compounds into broad-spectrum antibiotics via addition of a primary amine, all are consistent with the eNTRy rules. (B) Two examples of conversions to broad-spectrum antibiotics that are not consistent with the eNTRy rules, both converted compounds are diamines and may enter Gram-negative bacteria through the self-promoted uptake pathway. RB = rotatable bonds; Glob = globularity; Broad-spectrum = activity against both Gram-positive and Gram-negative bacteria; PA = P. aeruginosa; MIC = minimum inhibitory concentration.