Self-assembled ph-responsive Polymeric Micelles for Highly. Efficient, Non-Cytotoxic Delivery of Doxorubicin Chemotherapy

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1 Supporting Information Self-assembled ph-responsive Polymeric Micelles for Highly Efficient, on-cytotoxic Delivery of Doxorubicin Chemotherapy to Inhibit Macrophage Activation: In Vitro Investigation Zhi-Sheng Liao, a Shan-You Huang, a Jyun-Jie Huang, a Jem-Kun Chen, b Ai-Wei Lee, c Juin-Yih Lai, aef Duu-Jong Lee, def and Chih-Chia Cheng a * a. Graduate Institute of Applied Science and Technology, ational Taiwan University of Science and Technology, Taipei 10607, Taiwan. cccheng@mail.ntust.edu.tw b. Department of Materials Science and Engineering, ational Taiwan University of Science and Technology, Taipei 10607, Taiwan. c. Department of Anatomy and Cell Biology, School of Medicine, College of Medicine, Taipei Medical University, Taipei 11031, Taiwan. d. Department of Chemical Engineering, ational Taiwan University, Taipei 10617, Taiwan. e. Department of Chemical Engineering, ational Taiwan University of Science and Technology, Taipei 10607, Taiwan. f. R&D Center for Membrane Technology, Chung Yuan Christian University, Chungli, Taoyuan 32043, Taiwan. S1

2 Experimental Section C C + 3 H CH 3 x H 3 MDI PPG dibutyltin dilaurate H H CH 3 x dry THF, 50 o C PU- 3 n x = 14 n = 13 H 3 C y Propargyl PEG4000 (or Propargyl PEG2000) CuBr, PMEDTA DMAc, 50 o C H H 3 C y H CH 3 x n x = 14 y = 45 & 90 n = 13 CH3 y PU-PEG4T or PU-PEG2T Scheme S1. Synthetic procedures for PU-PEG. Synthesis of azide-grafted polyurethane (PU- 3 ) PPG- 3 [49] (3 g, 4 mmol) was dissolved in dry THF (70 ml) then purged with dry nitrogen for 30 min. 4,4'-Methylenediphenyl isocyanate (MDI; 1.09 g, 4 mmol) and one drop of dibutyltin dilaurate were added dropwise using a syringe, and the mixture was magnetically stirred at 50 C under nitrogen for 16 h. After polymerization, an excess of anhydrous methanol (4 g, 25 mmol) was added and the solvents were sequentially evaporated using a rotary evaporator. Finally, the reaction residue was poured into a large amount of methanol to precipitate a light-yellow product. Yield: 84% (3.44 g). S2

3 Synthesis of PEG-functionalized polyurethane (PU-PEG) Monopropargyl-terminated PEG2T and PEG4T were synthesized as previously reported [50]. Azide-grafted PU- 3 (0.1 g, 6.58 µmol) and monopropargyl-terminated PEG4T (0.79 g, µmol) or PEG2T (0.395 g, µmol) were dissolved in dimethylacetamide (DMAc; 80 ml) and the mixture was purged with dry nitrogen for 30 min. CuBr (10 mg, 71 µmol) and pentmethyl diethylenetriamine (PMDETA; 13 µl, 60 µmol) were added to the reactor, then degassed over four freeze/thaw evacuation cycles, then the reaction mixture was heated at 50 C for 24 h under nitrogen, cooled to ambient temperature, passed directly through a neutral alumina column to remove the copper catalyst, and purified by dialysis against deionized water in cellulose dialysis membrane (molecular weight cut-off, MWC Da) for 3 days. Finally, the remaining water was removed by vacuum distillation to yield the final product (yield = 91% for PU-PEG4T and 93% for PU-PEG2T). S3

4 Figure S1. 1 H MR spectrum of PPG- 3 in deuterated chloroform (CDCl 3 ) at 20 C. S4

5 Figure S2. 1 H MR spectrum of PU- 3 in CDCl 3 at 20 C. S5

6 Figure S3. 1 H MR spectrum of PU-PEG4T in CDCl 3 at 20 C. S6

7 Figure S4. 1 H MR spectrum of PU-PEG2T in CDCl 3 at 20 C. S7

8 Figure S5. SEC traces for PU- 3, PU-PEG2T and PU-PEG4T. S8

9 Figure S6. Determination of CMC for PU-PEG2T and PU-PEG4T in aqueous solution. S9

10 Figure S7. (a) Particle diameter and DX-loading content as a function of DX additive concentration for DX-loaded PU-PEG4T micelles in aqueous solution. (b) AFM, (c) SEM and (d) TEM images of PU-PEG4T micelles with a DX loading content of 8%. Inset: enlarged (c) SEM and (d) TEM images of DX-loaded PU-PEG4T micelles. S10

11 Figure S8. Particle size distribution of DX-loaded PU-PEG4T micelles over time at ph 4.0 and 37 C. S11

12 Figure S9. Particle size distribution of doxorubicin hydrochloride (0.005 mg/ml) in PBS at ph 4.0 and 37 C. S12

13 Figure S10. Viability of RAW cells after 24 h incubation with different concentrations of PU-PEG2T and PU-PEG4T in PBS, ph 7.4, at 37 C. S13

14 Figure S11. CLSM images of RAW cells incubated with DX-loaded PU-PEG4T micelles (DX loading = 9.1%) for 4, 8 or 24 h at ph 7.4 and 37 C. RAW cells were stained with DAPI as a nuclear stain (blue fluorescence). DX emits characteristic red fluorescence at nm when excited at 480 nm. The upper and middle panels are the bright-field and fluorescence images, respectively; the lower panel is the merged images for all fluorescence channels. Scale bar = 20 µm for all images. S14

15 Figure S12. Flow cytometric analysis of apoptosis in Annexin V/PI stained RAW cells incubated with DX-loaded PU-PEG4T micelles (DX loading = 9.1%) at 37 C and ph 4.0 for (a) 4 h, (b) 8 h or (c) 24 h. S15

16 Table S1. Zeta potentials of the blank and DX-loaded PU-PEG4T micelles (DX loading = 9.1%) in aqueous solution at 25 C. Sample Zeta potential (mv) PU-PEG 4T DX-loaded PU-PEG4T Table S1 implies the significantly increased zeta potentials enabled the DX-loaded PU-PEG4T micelles to stably disperse in aqueous solution, which can possibly be attributed to presence of some specific intermolecular interactions between the DX molecules and aromatic groups of the PU backbone, leading to a deep penetration of the DX into micellar interior. The generated DX-loaded PU-PEG4T micelles in aqueous solution (-22.6 mv) had a more negative zeta potentials than pure PU-PEG4T in aqueous solution (-7.31 mv) due to electrostatic repulsion between DX and micelles or increased ion-pair formation between DX with solute ions, resulting in increased stability of the DX-loaded micellar dispersions. S16

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