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. 2022 May 25;61(29):e202203995. doi: 10.1002/anie.202203995

Figure 7.

Figure 7

Effects of arene crosslink on membrane and cell uptake of helix‐constrained peptides. A) Stapled pDI peptides 7  a–d and 8, modified at the N‐terminus with FITC‐βAla‐. B) CD spectra of peptides (20 μM) in 0.5 mM POPC vesicles, 10 mM HEPES/10 mM NaCl buffer pH 7.4. C) Fractional partition in 1‐octanol/10 mM phosphate buffer pH 7.4 (1 : 1, v/v) used to determine logD7.4 (top row, mean n≥2). D) Partition coefficients (K p) from binding curves of titration with POPC or POPC : POPS (4 : 1) vesicles in 10 mM HEPES, 10 mM NaCl pH 7.4 buffer followed by FP. Error bars=mean±SD. E) Percent (mean±SEM) uptake of peptides 7  a–d vs 8 (5 μM, 1 h) into HeLa cells measured by flow cytometry. Fluorescence normalized to TAT (5 μM) as 100 % uptake, 37 °C. F) Uptake of 7  d in presence of endocytosis inhibitors: 4 °C (active endocytosis); 50 μM EIPA (macropinocytosis); 50 μM Dynasore or 10 μM Chlorpromazine (clathrin‐mediated endocytosis); or 500 μM Genistein (caveolin‐mediated endocytosis). One‐way ANOVA, P values: * (P=0.01), *** (P<0.001), **** (P<0.0001), ns (not significant) vs 7  a (E) or vs no inhibitor (F).