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1 Supporting Information Structural Engineering of Biodegradable PCL Block Copolymer Nano-assemblies for Enzyme-Controlled Drug Delivery in Cancer Cells Bapurao Surnar and Manickam Jayakannan* 1 Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pune , Maharashtra, INDIA Table of content 1. Synthesis of diblock copolymers S H-NMRs of block copolymers. S C NMRs of block copolymers. S4 4. FTIR of block copolymers. S5 5. GPC chromatograms of block copolymers S6 6. Table of molecular weights S7 7. TGA profiles of diblock copolymers S7 8. VT - 1 H-NMR of PEG-b-PCLAC 8 S8 9. DLS histograms of diblock Nano assemblies S9 10. FESEM and AFM images of diblock Nano assemblies S DLS histograms of PEG-b-PCLAC 8 S CAC of diblock copolymers S DLS histograms of DOX loaded diblock Nano assemblies S FESEM images of DOX loaded diblock Nano assemblies S Cumulative release of PEG-b-BPCL-DOX nanoparticles S Stack plot of FTIR spectra S CLSM images of free DOX in HeLa and MCF 7 cells. S CLSM images of DOX loaded nanoparticles in MCF 7 cells (12 h) S Cumulative release of multi-drug loaded PEG-b-BPCL nanoparticles S16 1 Corresponding author: jayakannan@iiserpune.ac.in S1
2 Synthesis of Diblock Copolymers: Synthesis of PEG-b-PCLAC 8 diblock polymer: Monomer 7a (760 mg, 2.43 mmol), initiator PEG 2000 (48.5 mg, mmol) and catalyst Sn(Oct) 2 (4.9 mg, mmol). Yield = 570 mg (75 %). 1 H NMR (400 MHz, CDCl 3 ) δ ppm: 6.36 (br, -NH), 4.13 (m, 2 H), (m, 5.32 H), 3.43 (m, 1 H), 3.21 (m, 2 H), 2.39 (m, 2 H), (m, 4 H), 1.48 (m, 2 H), 1.26 (m, 10 H), 0.86 (t, 3 H). 13 C NMR (100 MHz, CDCl 3 ): 173.7, 171.4, 76.1, 70.2, 65.5, 61.1, 59.2, 39.6, 37.2, 32.7, 31.6, 29.0, 26.8, 22.7 and FT-IR (cm 1 ): 3320, 3089, 3089, 2918, 2947, 1642, 1531, 1480, 1353, 1249, 1172, 1104, 957, 735, and 641. GPC molecular weights: M n = 10,000, M w = 14,100 and M w /M n = Synthesis of PEG-b-BPCL diblock polymer: Monomer 3 (1.0 g, 3.87 mmol), initiator PEG 2000 (193.8 mg, mmol) and catalyst Sn(Oct) 2 (7.8 mg, mmol). Yield: 700 mg (70 %). 1 H NMR (400 MHz, CDCl 3 ) δ ppm: 4.13 (s, 2 H), 3.63 (s, 6.51 H), 3.43 (s, 1 H), 3.38 (s, 1 H), 2.44 (t, 2 H), 2.35 (t, 2 H), (m, 2 H), (m, 4 H), 1.44 (s, 9 H, t-butyl). 13 C NMR (100 MHz, CDCl 3 ): , , 80.77, 75.62, 70.66, 65.13, 61.47, 36.60, 33.04, 29.81, 28.86, and FT-IR (cm 1 ): 2973, 2931, 1727 (C=O ester), 1457, 1364, 1251, 1156, 1156, 1100, 1062, 959, 900, 845, and 757. GPC molecular weights: M n = 13,000, M w = 17,100 and M w /M n = Synthesis of PEG-b-PCL diblock polymer: Caprolactone (0.5 g, 4.39 mmol), mpeg-2k (87.8 mg, mmol) and Sn(Oct) 2 (8.8 mg, mmol). Yield: 450 mg (90%). 1 H NMR (400 MHz, CDCl3) δ ppm: 4.06 (t, 2 H), 3.64 (s, 1.78 H), 2.31 (t, 2.1 H), (m, 4 H), 1.38 (t, 2 H). FT-IR (cm-1): 3648, 2944, 2867, 2365, 1722, 1649, 1514, 1464, 1365, 1292, 1239, 1174, 1102, 958, 839 and 728. GPC molecular weights: Mn = 12,500, Mw = 14,000 and Mw/Mn= S2
3 Figure S1: Stack plot of 1 H NMRs of diblock copolymers Note: The stack plot of 1 H NMRs of polymers are provided. The protons f in the diblocks appeared along with protons d of PEG. The intensities of protons e in the ester OCH 2 - appeared at 4.13 ppm. Thus, the subtraction of peak intensities [(e+f) a] provided the actual number of protons e. The comparison of peak integrals of a (protons at 3.63 ppm) with protons e (at 4.13 ppm) provided the number average degree of polymerization (n) for the PCL backbone in the diblock structure. The number average molecular weights (M n ) were calculated (M n = n X repeating unit mass) and tabled in Table S1 below. S3
4 Figure S2: Stack plot of 13 C NMRs of diblock copolymers S4
5 Figure S3: FTIR profles of diblock copolymers with their respective corbonyl peaks S5
6 Figure S4: GPC chromatograms and plot of molecular weights and polydispersity index of diblock copolymers. Note: The molecular weights of the diblocks were determined by GPC (Gel permeation chromatography) using polystyrene standard in THF as eluent. As shown above, GPC chromatograms of all block copolymers showed monomodal distribution and confirmed the formation of high molecular weight polymers. Molecular weights and polydispersity index (PDI) determined from GPC are tabled in Table S1. The molecular weights from NMR and GPC and PDI from GPC have been plotted and shown above, GPC underestimated the molecular weights. This might be attributed to the hydrodynamic radius of diblocks in THF. Polydispersities were ranging from 1.2 to 1.4, which proved the formation of narrow molecular weight polymers. S6
7 Table S1: Molecular weights (NMR and GPC) of diblock copolymers Figure S5: TGA profiles of diblock copolymers. S7
8 Figure S6: Variable temperature 1 H NMR of PEG-b-PCLAC 8 in DMSO-d6 for cooling cycle. S8
9 Figure S7: DLS histograms of diblock copolymer nano-assemblies in milli-q water. Note: DLS histograms in de-ionized water indicate the mono-modal distribution for diblock polymer nano-assemblies with the average size of 90 to 130 nm. S9
10 Figure S8: FESEM and AFM image of PEG-b-PCLAC 8 diblock copolymer nano-assemblies in milli-q water. Note: FESEM (Field emission scanning electron microscope) (a) and AFM (atomic force microscopy) (b) were carried out for diblock copolymers in DI water with 0.2 mg/ml at 25 o C. FESEM image and AFM image of PEG-b-PCLAC 8 showed the diblock polymer as 115 ± 20, 130 ± 20 nm size soft spherical particles respectively. Sizes of the images are in good coherence with DLS data. S10
11 Figure S9: DLS histograms of PEG-b-PCLAC 8 diblock copolymer nanoassemblies in PBS (ph = 7.4) for 7 days. Note: In order to scrutinise the stability of these diblock nano-assemblies in PBS (ph = 7.4), samples were subjected to DLS up to 7 days. In this experiment, the diblock concentration was maintained at 0.2 mg/ml at 37 o C. The histograms representing the PEG-b-PCLAC 8 diblock nano-assembly showed no change in size and proved that the formed nano-assemblies were very stable in PBS up to a week. S11
12 Figure S10: Plots I 3 /I 1 vs concentration of diblocks. Note: Critical association concentration (CAC) of PEG-b-PCLEC 8, PEG-b-BPCL and PEG-b- PCLAC 8 were determined using pyrene as a fluorescent probe. The emission (mainly I 1 and I 3 ) intensity is sensitive to its hydrophobic and hydrophilic environment. The ratio of fluorescence intensity at I 3 (386 nm) to I 1 (375 nm) was determined and plotted against the concentration to obtain critical association concentration. CAC for PEG-b-PCLEC 8, PEG-b-BPCL and PEG-b- PCLAC 8 were determined as 2.6, 5.0, and 5.2 µg/ml respectively. S12
13 Figure S11: DLS histograms of DOX-loaded diblock copolymer nano-assemblies in milli-q water. Note: DLS histograms of DOX-loaded diblock assemblies in de-ionized water showed monomodal distribution pattern and the average size observed was obtained as nm. This showed a slight increase in the particle size after the loading of DOX. Figure S12: FESEM images of DOX-loaded diblock copolymer nano-assemblies in milli-q water. Note: FESEM images of PEG-b-PCLAC 8 -DOX (a) and PEG-b-BPCL-DOX (b) diblock polymers provide 130, 140 nm size soft spherical particles, respectively. S13
14 Figure S13: Cummulative releses profiles of PEG-b-BPCL in ph = 5.0, 7.4 and in presence of esterase in PBS at 37 o C. Figure S14: Stack plot of FTIR spectra of free DOX and DOX loaded nanoparticles. S14
15 Figure S15: CLSM images of free DOX in HeLa and MCF 7 cell lines nanoparticles. Note: In HeLa cells line free DOX was found to be accumulated in the cytoplasm as well as at nucleus. On the other hand, in MCF 7 cell line, the free DOX predominantly accumulated in the nucleus (magenta color). Figure S16: CLSM images of DOX loaded nanoparticles in MCF 7 cells after 12 h incubation. S15
16 Figure S17: DLS histogrram of PEG-b-BPCL-DOX (a) and Cummulative releses profiles (b) of multi-drug loaded PEG-b-BPCL nanoparticles in ph = 7.4 (PBS) at 37 o C. S16
17 Figure S18: 1 H-NMR and 13 C-NMR of compound (1) S17
18 Figure S19: 1 H-NMR and 13 C-NMR of compound (2) S18
19 Figure S20: 1 H-NMR and 13 C-NMR of compound (3) S19
20 Figure S21: 1 H-NMR and 13 C-NMR of compound (4) S20
21 Figure S22: 1 H-NMR and 13 C-NMR of compound (5a) S21
22 Figure S23: 1 H-NMR and 13 C-NMR of compound (5b) S22
23 Figure S24: 1 H-NMR and 13 C-NMR of compound (6) S23
24 Figure S25: 1 H-NMR and 13 C-NMR of compound (7) S24
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