Cytosolic targeting of macromolecules using a ph-dependent fusogenic peptide in. combination with cationic liposomes
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1 Cytosolic targeting of macromolecules using a ph-dependent fusogenic peptide in combination with cationic liposomes Sachiko Kobayashi, Ikuhiko Nakase, Noriko Kawabata, Hao-hsin Yu, Silvia Pujals, Miki Imanishi, Ernest Giralt,,# and Shiroh Futaki, * Institute for Chemical Research, Kyoto University, Uji, Kyoto , Japan Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona, Spain # Department of Organic Chemistry, University of Barcelona, Martí i Franquès 1-11, Barcelona, Spain Supporting Information Peptide Synthesis and Fluorescence Labeling. All the peptides in this report were chemically synthesized by Fmoc (9-fluorenylmethyloxycarbonyl) solid-phase peptide synthesis on Rink amide resin using the standard protocol of a Shimadzu PSSM-8 peptide synthesizer as previously reported (15). For the coupling system, a combination of S1
2 benzotriazole-1-yloxytrispyrrolidinophos-phonium hexafluorophosphate (PyBOP), 1-hydroxy-benzotriazole (HOBt), and 4-methylmorpholine (NMM) was employed. Treatment of the peptide resin with trifluoroacetic acid (TFA)-ethanedithiol (EDT) (95:5) for the cleavage of the peptide from the resin and deprotection of the peptides at 25 C for 3 h and high-performance liquid chromatography (HPLC) purification of the deprotected sample gave a pure peptide. The fidelity of the products was confirmed by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOFMS). Amino acid sequences and characterization of the synthesized peptides: GALA peptide, WEAALAEALAEALAEHLAEALAEALEALAA-amide, MALDI-TOFMS: [calcd. for (M+H) + : ]; scrambled GALA (sgala) peptide, AAALHAALAAEAELLEEWLAAEEAELLAAA-amide, MALDI-TOFMS: [calcd. for (M+H) + : ]. CG-GALA, CG-WEAALAEALAEALAEHLAEALAEALEALAA-GG-PKKKRKV-amide, MALDI-TOFMS: [calcd. for (M+H) + : ]. For the preparation of the fluorescently labeled peptides, a γ-aminobutyryl (GABA) residue was attached to the N-terminus of the peptide resin as a spacer for S2
3 connecting with a fluorescence label, and then the N-terminus of the resin was treated with fluorescein-5-isothiocyanate (Sigma) and N-ethyldiisopropylamine (DIEA) (3 eq. each to the peptide resin) in N, N-dimethylformamide (DMF) at 25 C for 3 h. The fluorescein labeled peptide resin was treated with TFA-EDT (95:5), purified, and identified as stated above. Amino acid sequences and characterization of the synthesized peptides: peptide, FITC-NH-(CH 2 ) 3 -CO-WEAALAEALAEALAEHLAEALAEALEALAA-amide, MALDI-TOFMS: [calcd. for (M+H) + : ]; FITC-scrambled GALA (FITC-sGALA) peptide, FITC-NH-(CH 2 ) 3 -CO-AAALHAALAAEAELLEEWLAAEEAELLAAA-amide, MALDI-TOFMS: [calcd. for (M+H) + : ]. For the preparation of biotinylated-gala peptide (biotin-gala) and biotinylated-scrambled GALA peptide (biotin-sgala), the GABA residue was attached to the N-terminus of the peptide resin as a space followed by the treatment with biotinamidocaproate N-hydroxysuccinimide ester (Sigma) in the presence of DIEA (3 eq. each to the peptide resin) in DMF at 25 C for 20 h. Biotinylated-GALA peptide S3
4 having the nuclear localization signal sequence, derived from SV40 T antigen, on its C-terminus (biotin-gala-nls) was similarly synthesized as stated; the Gly-Gly segment was inserted here between GALA sequences and NLS sequences as a spacer. The products were purified and analyzed as stated above. Amino acid sequences and characterization of the synthesized peptides: biotinylated-gala peptide, biotinamidocaproyl- NH-(CH 2 ) 3 -CO-WEAALAEALAEALAEHLAEALAEALEALAA-amide, MALDI- TOFMS: [Calcd. for (M+H) + : ]; biotin-gala-nls, biotinamidocaproyl- NH-(CH 2 ) 3 -CO-WEAALAEALAEALAEHLAEALAEALEALAA-GG-PKKKRKV-am ide, MALDI-TOFMS: [calcd. for (M+H) + : ]; biotinamidocaproyl-scrambled GALA peptide (biotin-sgala), biotinamidocaproyl- NH-(CH 2 ) 3 -CO-AAALHAALAAEAELLEEWLAAEEAELLAAA-amide, MALDI-TOFMS: [calcd. for (M+H) + : ]. The conditions and the retention time for the synthesized peptides were following: column, Cosmosil Protein R ( mm); gradient: 45-85% B in A over 40 min (A = H 2 O containing 0.1% (v/v) CF 3 COOH, B = CH 3 CN containing 0.1% (v/v) S4
5 CF 3 COOH); flow, 1.0 ml/min; detection, 215 nm. GALA, 17.2 min; sgala, 5.3 min; GC-GALA, 20.1 min;, 22.8 min; FITC-sGALA, 13.2 min; biotin-gala, 21.5 min; biotin-gala-nls, 13.6 min, biotin-sgala, 10.9 min. S5
6 (A) CHO-K1 0.5 µm 1 µm 5 µm 10 µm 0.5 µm 1 µm 5 µm 10 µm 0.5 µm 1 µm 5 µm 10 µm 0.5 % (v/v) 1 % (v/v) 2 % (v/v) (B) A % (v/v) 1 % (v/v) 2 % (v/v) (C) NIH3T3 0.5 % (v/v) Figure S1. Effect of GALA/ ratios in cytosolic targeting of FITC as a model of membrane impermeable molecules. Cell, CHO-K1 (A), A431 (B), NIH3T3 (C). Scale bars, 20 µm. Incubation, 4 h. 1 % (v/v) 2 % (v/v) S6
7 1.0 µm 10 µm 0.5 % (v/v) Lipofectin 1 % (v/v) Lipofectin Figure S2. Effect of concentration of GALA and Lipofectin on the cellular distribution of the FITC signals. HeLa cells were treated with in the presence of Lipofectin in α-mem without containing serum for 6 h. Scale bars, 100 µm. (A) FITC FITC DIC 37 4 (B) +NH4Cl +nocodazole FITC DIC FITC DIC Figure S3. Involvement of endocytosis and importance of endosomal acidification for this cytosol targeting system. (A) HeLa cells were incubated with (1 µm) in the presence of 1 % (v/v) in α- MEM(+) at 37 C or 4 C for 2 h, respectively, and analyzed by confocal microscopy after PBS wash. Scale bars, 20 µm. (B) HeLa cells were incubated with 1 µm /1%(v/v) in the presence of NH 4 Cl (50 mm) or nocodazole (20 µm) in α-mem(+) at 37 C for 2 h. Scale bars, 50 µm. S7
8 (A) HeLa EGFP DIC merge EGFP-GALA + EGFP-GALA (B) CHO-K1 EGFP DIC merge EGFP-GALA + EGFP-GALA Figure S4. Application of GALA/ system to cytosolic targeting of EGFP. (A) Confocal microscopic observation of HeLa cells treated with 2 µm EGFP-GALA and 4% (v/v) for 8 h. (B) CHO-K1 cells were treated with 0.5 µm EGFP-GALA and 1% (v/v) for 8 h. Efficient cytosolic diffusion of EGFP- GALA was not observed in the absence of. S8
9 (A) QD FAST DiI merge (B) +biotin-gala + +biotin-sgala + Colocalization with FAST DiI (%) sgala GALA (C) QD Lysotracker merge (D) +biotin-gala + +biotin-sgala + Colocalization with Lysotracker (%) (E) QD FAST DiI merge (F) sgala GALA +biotin-gala + +biotin-sgala + Colocalization with FAST DiI (%) sgala GALA Figure S5. (A, C, E) Confocal microscopic observation of HeLa cells treated with the complex of (2 nm), 1% (v/v) and biotin-gala or biotin-sgala (1 µm each) for 6 h in the presence of FAST DiI (A) and Lysotracker (C), and 24 h in the presence of FAST DiI (E), respectively. FAST DiI was added to the medium 6 h prior to the microscopic observation. (B, D, F) Statistical analysis of colocalization of the signal with that of FAST DiI or Lysotracker. HeLa cells were similarly treated with /biotin-sgala/ (left column) or /biotin- GALA/ (right column) for 6 h (B, D) or 24 h (F). The total number of dots showing the signal in the cells and the merged ones with the signals of Lysotraker or FAST DiI were manually counted (931, 1405, and 1210 counts for /biotin-sgala/-treated cells, and 1180, 632, and 883 counts for /biotin-gala/-treated cells, respectively). Scale bars, 20 µm. At 6 h, over 50% of signals overlapped with those of FAST DiI, suggesting that a considerable portion of were trapped in early endosomes (B), whereas only 20% of localized in lysosomes (D). At 24 h, those overlapping with FAST DiI became 20%, suggesting the escape of to cyotosol or the shift to lysosomes. S9
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