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1 Supporting Information Multistimuli-Responsive Supramolecular Vesicles Based on Water-Soluble Pillar[6]arene and SAINT Complexation for Controllable Drug Release Yu Cao, Xiao-Yu Hu, Yan Li, Xiaochun Zou,, Shuhan Xiong, Chen Lin, Ying-Zhong Shen, and Leyong Wang* Key Laboratory of Mesoscopic Chemistry of ME, Center for Multimolecular rganic Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing (China). State Key Laboratory of Bioelectronics and Jiangsu Key Laboratory of Biomaterials and Devices, School of Biological Science and Medical Engineering, Southeast University, Nanjing (China). College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing (China). Supporting Information (13 pages) 1. Job plot for WP6 G...S2 2. 2D NESY spectrum of WP6 G in D 2.S2 3. UV-Vis absorption spectroscopy studies of the aggregation behaviors...s3 4. ζ-potentials of the aggregates formed by WP6 G or G...S3 5. Investigation of the interactions between WP6 and G...S3 6. Raw ITC data of WP6 with G in water at different temperature...s4 7. Investigation of the morphology of the calcein-loaded vesicles...s5 8. ph-responsive calcein release profiles of the calcein-loaded vesicles...s5 9. DLS data of the WP6 G aggregates at 20 and after heating...s5 10.ζ-potential and the stability of the WP6 G vesicles after heating...s5 11. Investigation of the Ca 2+ -induced vesicle fusion process by using ITC experiments...s6 12. DLS data of Ca 2+ induce WP6 G vesicle fusion...s7 13. Fluorescence changes of the membrane probes CERB during the vesicle fusion process...s8 14. Synthesis of water-soluble pillar[6]arene (WP6), guest molecules (G and G ), and the membrane probe CERB...S8 15. The structure and preparation of the desalted doxorubicin (DX)...S References S13 S1

2 1. Job plot for WP6 G Figure S1. (a) UV-Vis absorption of the mixture of WP6 and G in water (containing 4% EtH to improve the solubility of G) at different molar ratios (from [G]/[WP6] = 9:1 to [G]/[WP6] = 1:9) with a constant concentration of [WP6] + [G] = M. (b) Job plot showing the 1:1 stoichiometry of the complex between WP6 and G by plotting the difference in absorption at 290 nm (a characteristic absorption peak of WP6) against the mole fraction of G at an invariant total concentration of M in aqueous solution. 2. 2D NESY spectrum of WP6 G in D 2 Figure S2. 2D NESY spectrum of WP6 G (400 MHz, D 2, 298 K), [WP6] = 10.0 mm, [G ] = 30.0 mm. S2

3 3. UV-Vis absorption spectroscopy studies of the aggregation behaviors Figure S3. (a) UV-Vis absorption spectra of the aqueous solutions of WP6 at different concentrations in the presence of mm of G at 20 C. (b) Dependence of the absorbance at 350 nm on WP6 concentration with a fixed G concentration (0.146 mm) at 20 C. 4. ζ-potentials of the aggregates formed by WP6 G or G Figure S4. (a) The zeta potentials of the aggregates formed by WP6 G at different molar ratio of [WP6]/[G] (with constant G concentration ( mm) by increasing the concentration of WP6). (b) The zeta potentials of the aggregates formed by G. (c) The zeta potentials of the aggregates formed by WP6 G, which was suitable for further investigation of their stimuli-responsive behavior as well as their application in drug delivery. 5. Investigation of the interactions between WP6 and G The association constant between WP6 and G was determined in H 2 by using isothermal titration calorimetry (ITC). A representative calorimetric titration curve was shown in Figure S5. Based on the obtained ITC data, the association constant (K a ) of WP6 G was estimated to be (1.67 ± 0.13) 10 5 M 1. S3

4 Figure S5. Microcalorimetric titrations of WP6 with G in water at K. (a) Raw ITC data of microcalorimetric titrations for 35 sequential injections (1.1 μl per injection) of WP6 solution (2 mm) into the aqueous solution of G (0.2 mm); (b) S-type heat effects of the complexation between WP6 and G for each injection, obtained by subtracting the dilution heat from the reaction heat, which was fitted by computer simulation using the one set of binding sites model. 6. Raw ITC data of WP6 with G in water at different temperature From the calorimetric titration curves obtained at different temperature (Figure S6), it was found that the association constants of WP6 G were rapidly reduced with the increase of temperature, and the host-guest interaction between WP6 and G was totally destroyed at 28 C, indicating the thermal-responsiveness of the above supramolecular WP6 G complex. Figure S6. Raw ITC data of microcalorimetric titrations for 29 sequential injections (10 μl per injection) of WP6 solution (0.1 mm) into the aqueous solution of G (0.01 mm) at different temperature. S4

5 7. Investigation of the morphology of the calcein-loaded vesicles Figure S7. (a) TEM images of calcein-loaded vesicles. (b) DLS data of the calcein-loaded vesicles. 8. ph-responsive calcein release profiles of the calcein-loaded vesicles Figure S8. ph-responsive calcein release profiles of the calcein-loaded vesicles at different ph buffers. 9. DLS data of the WP6 G aggregates at 20 C and after heating Figure S9. DLS data of the WP6 G aggregates at 20 C (a) and after heating at 36 C for 5 min (b). 10. ζ-potential and the stability of the WP6 G vesicles after heating S5

6 Figure S10. (a) ζ-potential of the WP6 G vesicles after heating; (b) the fluorescence intensity of calcein-loaded vesicles after heating for different times (1-48 h). 11. Investigation of the Ca 2+ -induced vesicle fusion process by using ITC experiments In order to further understand the mechanism accounting for the fusion process, we have performed additional ITC experiment to investigate the binding affinity of WP6 and Ca 2+, which might be an important inducement for the vesicles fusion. As shown in Figure R1, the heat effect and the bonding affinity between WP6 and Ca 2+ could be obtained from the calorimetric titration curves, where the association constant of WP6-Ca 2+ was estimated to be (1.56 ± 0.103) 10 4 M 1, indicating a strong binding between WP6 and Ca 2+. Moreover, ITC data also showed that the heat effect accompanying the binding of Ca 2+ to the carboxylate groups of WP6 in aqueous solutions was an endothermic process, which was driven by an unfavorable enthalpy change ( H o = kcal mol -1 ) and a positive entropy change (T S o = kcal mol -1 ), suggesting this was an entropy-driven process. Furthermore, DLS experiments showed that the average diameters of vesicles increased sharply with the time extension. And the TEM images and binary mixing assays using the Cetyl Rhodamine B (CERB) probe further confirmed that the ultimate merging of the bilayers happened. Therefore, based on the above observation and detailed investigation of the related literatures, S1 the WP6 G vesicle fusion process should be dissected into the following three well-defined processes: firstly, Ca 2+ binding to the carboxylate headgroups of WP6, which exist in the outside surface of the WP6 G vesicles; and then, such Ca 2+ -WP6 binding further induced the vesicle aggregation; ultimately, merging of the bilayers resulted in the vesicle fusion, which accompanied with the contents release. S6

7 Figure S11. Microcalorimetric titrations of WP6 with Ca 2+ in water at K. (a) Raw ITC data of microcalorimetric titrations for 19 sequential injections (2.0 μl per injection) of CaCl 2 solution (5 mm) into the aqueous solution of WP6 (0.2 mm); (b) S-type heat effects of the complexation between WP6 and Ca 2+ for each injection, obtained by subtracting the dilution heat from the reaction heat, which was fitted by computer simulation using the one set of binding sites model. 12. DLS data of Ca 2+ induce WP6 G vesicle fusion Figure S12. (a) Mean diameter changes of the vesicles at different times. DLS data of the Ca 2+ induced WP6 G vesicle fusion at different times: (b) 0 min, (c) 1 min, (d) 3 min, and (e) 8 min. S7

8 13. Fluorescence changes of the membrane probes CERB during the vesicle fusion process Figure S13. Fluorescence changes of CERB in vesicular solution with the presence of Ca 2+ (5 mm) at 25 C after standing for different times (0 8 min). 14. Synthesis of water-soluble pillar[6]arene (WP6), guest molecules (G and G ), and the membrane probe CERB Water-soluble pillar[6]arene (WP6) was prepared according to previously reported method S2 and the synthetic procedure was shown in Scheme S1. H H H H H BBr 3 dry CHCl 3 H H H H H Br Et K 2 C 3,NaI H H R R R R R R R R NaC CNa NaC CNa R NaC CNa R NaH, H 2 NaC CNa R NaC CNa R NaC CNa R= Et WP6 Scheme S1. Synthetic route for water-soluble pillar[6]arene (WP6). Guest molecule (G) was prepared according to previously reported method S3 and the synthetic procedure was shown in Scheme S2. Scheme S2. Synthetic route for guest molecule G. S8

9 General procedure (synthesis of guest G): A solution of lithium diisopropylamide (LDA) in dry THF (10 ml, 0.02 mol) was slowly added dropwise to the solution of freshly distilled 4-methylpyridine (0.93 g, 0.01 mol) in dry THF (10 ml) which was cooled to -45 C before. The mixture was stirred at -45 C for 1 h, then n-hexadecyl bromide (6.1 g, 0.02 mol) dissolved in THF (5 ml) was added dropwise to the above mixture. The reaction mixture was first stirred at -45 C for 1 h, and then was continually stirred for 12 h at 25 C. Subsequently, ether (20 ml) was added and the reaction mixture was washed twice with a 1 M NH 4 Cl aqueous solution (30 ml), dried over Na 2 S 4, and the solvent was removed under vacuum. The product 1 was crystallized from acetone and collected by filtration, and dried under vacuum. Then the resulting product 1 (5.0 g, mol) were reacted with an excessive amount of CH 3 I (3 ml, mol) at refluxing temperature in acetone for 24 h. After the solvent was removed under vacuum, and the target product G (6.5 g, 60%) was purified by crystallization using ethanol (15 ml). 1 H NMR (300 MHz, CDCl 3 ) δ (ppm): 9.20 (d, J = 6.6 Hz, 2H), 7.75 (d, J = 6.6 Hz, 2H), 4.69 (s, 3H), (m, 1H), (m, 4H), (m, 52H), 1.07 (brs, 4H), 0.88 (t, J = 6.7 Hz, 6H). Figure S14. 1 H NMR spectrum of G (300 MHz, CDCl 3, 298 K). Guest molecule (G ) was also prepared according to previously reported method S3 and the synthetic procedure was shown in Scheme S3. S9

10 Scheme S3. Synthetic route for guest molecule G. General procedure (synthesis of guest G ): A solution of lithium diisopropylamide (LDA) in dry THF (10 ml, 0.02 mol) was slowly added dropwise to the solution of freshly distilled 4-methylpyridine (0.93 g, 0.01 mol) in dry THF (10 ml) which was cooled to -45 C before. The mixture was stirred at -45 C for 1 h, and then bromoethane (2.18 g, 0.02 mol) dissolved in THF (3 ml) was added dropwise to the above system. The reaction mixture was first stirred at -45 C for 1 h, and then was continually stirred for 12 h at 25 C. Subsequently, ether (20 ml) was added and the reaction mixture was washed twice with a 1 M NH 4 Cl aqueous solution (30 ml), dried over Na 2 S 4, and the solvent was removed under vacuum. Column chromatography was used in the final separation with petroleum ether/ethyl acetate (30:1, v/v) as the eluent to give compound 2 (1.5 g, 0.01 mol) as yellow oil. Then the resulting product 2 (1.5 g, 0.01 mol) was reacted with an excessive amount of CH 3 I (3 ml, mol) at refluxing temperature in acetone for 1 day. After the solvent was removed under vacuum, the resulting mixture was extracted with DCM (3 20 ml), and the aqueous phase was collected and the solvent was removed under vacuum. The product G was obtained as yellow solid (2.63 g, 90%). 1 H NMR (300 MHz, D 2 ) δ (ppm): 8.49 (d, J = 6.6 Hz, 2H), 7.74 (d, J = 6.6 Hz, 2H), 4.19 (s, 3H), (m, 1H), (m, 2H), (m, 2H), 0.64 (t, J = 7.4 Hz, 6H). S10

11 Figure S15. 1 H NMR spectrum of G (300 MHz, D 2, 298 K) The membrane probe CERB was prepared according to previously reported method S4 and the synthetic procedure was shown in Scheme S4. Scheme S4. Synthetic route for the membrane probe CERB. General procedure (synthesis of membrane probe CERB): In a 50 ml three-necked flask, a suspension of Rhodamine B (1.7 g, 3.5 mmol) in dry benzene (20 ml) was treated with dry pyridine (0.3 ml, 4.0 mmol), and then thionyl chloride (0.27 ml, 3.5 mmol) was added dropwise with stirring and cooling. The reaction mixture was stirred at 20 C for 12 h. Hexadecanol (1 g, 4 mmol) was then added and allowed to react for an additional 12 h with continued stirring. After benzene was removed under vacuum, the combined organic phases concentrated and purified by silica gel chromathography (dichloromethane/methanol/acetone, 200:15:5, v/v/v) to give CERB as a puce solid (0.35 g, 11.1%). 1 H NMR (300 MHz, acetone-d 6 ) δ 8.33 (d, J = 8.9 Hz, 1H), (m, 2H), 7.54 (d, J = 6.3 Hz, 1H), 7.17 (s, 4H), 7.01 (s, 2H), 3.97 (t, J = 6.4 Hz, 2H), (m, 8H), (m, 2H), 1.35 (d, J = S11

12 7.1 Hz, 12H), 1.28 (brs, 20H), 1.17 (brs, 4H), 1.05 (brs, 2H), 0.87 (t, J = 6.6 Hz, 3H). Figure S16. 1 H NMR spectrum of CERB (300 MHz, CDCl 3, 298 K) 15. The structure and preparation of the desalted doxorubicin (DX) The detailed procedure for the preparation of the desalted doxorubicin was shown in Scheme S5. Scheme S5. Preparation of the desalted doxorubicin. General procedure (preparation of desalted doxorubicin): DX HCl (5 mg, mm) was dissolved in CHCl 3 (3 ml), and then triethylamine (TEA, 10 μl) was added, the mixture was stirred in the dark at 25 C for 24 h. Finally, the solvent was removed under vacuum in the dark, and the desalted doxorubicin was obtained almost in 100% yield, which was directly used without further purification, and the contained TEA HCl was removed during the following dialysis process. S12

13 16. References S1. (a) Ravoo, B. J.; Kevelam, J.; Weringa, W. D.; Engberts, J. B. F. N. J. Phys. Chem. B, 1998, 102, (b) Ravoo, B. J.; Weringa, W. D.; Engberts, J. B. F. N. Cell Biol. Int., 2000, 24, 787. S2. Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han, C.; Huang, F. J. Am. Chem. Soc., 2012, 134, S3. Scarzello, M.; Wagenaar, A.; Stuart, M. C. A.; Hoekstra, D.; Engberts, J. B. F. N.; Hulst, R. J. Am. Chem. Soc., 2005, 127, S4. Keller, P. M.; Person, S.; Snipes, W. J. Cell. Sci. 1977, 28, S13

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