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. Author manuscript; available in PMC: 2020 Sep 1.
Published in final edited form as: Nat Chem Biol. 2019 Aug 19;15(9):889–899. doi: 10.1038/s41589-019-0336-0

Figure 5. Transmembrane permeation by TbAd analogs.

Figure 5.

a) Fluorescence spectroscopy assays of E. coli and M. smegmatis (M. smeg) inverted membrane vesicles (IMVs) used ATP or succinate to generate a pH gradient, followed by addition of the indicated compound. Four representative assays are shown from a total of 6 assays that found similar results and which were conducted in a blinded fashion. b-c) Liposomes with a neutral or acidic interior were treated with negative control compounds (adenosine, N6-TbAd), a positive control (chloroquine), or 1-TbAd, then subjected to size exclusion chromatography. Liposomes (black) were measured using absorbance at 600 nm, and chloroquine was measured at 342 nm. Adenosine-containing compounds were measured using MS. 1-TbAd at pH 5.0 differed significantly from all other treatments (p < 0.01) by least-squares means post test with adjustment by Tukey’s method after fitting a linear model and factorial ANOVA. d) Summary of cellular, IMV and liposome-based analysis of TbAd analogs identifies separate roles on the lipid carrier and proton trap site at the 1-position of adenosine.