Ultra Small Biocompatible Nanocomposites: A New Approach Using
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1 SUPPRTING INFRMATIN Ultra Small Biocompatible Nanocomposites: A New Approach Using Seeded Emulsion Polymerization for the Encapsulation of Nanocrystals Hauke Kloust, Elmar Pöselt, Sascha Kappen, Christian Schmidtke,,Andreas Kornowski, Werner Pauer, Hans-Ulrich Moritz, Horst Weller*, DLS data of hydrophobic iron oxide nanocrystals prior phase transfer Titel d (nm) Figure S-1. DLS data (intensity distribution) of hydrophobic iron oxide nanocrystals (11 nm) in Toluene. Stability of the composites A comparison of DLS data (intensity distribution) (Figure S-1) showing the measurement after synthesis (continuous line) and after storage for 7 months at room temperature (dashed line). No significant changes over time are observable.
2 Figure S-2. DLS Data (intensity distribution) comparing thee measurement of a sample after synthesis (continuouss line) and after 7-month storage att room temperature (dashed line). Figure S-3 shows a photograph of an iron oxide nanocrystal compositee 9 monthss after synthesis, stored at room temperature, showing a still homogeneous solution. Figure S-3. Photograph showing s ann iron oxide nanocrystal compositee 9 month after synthesis. Figure S-4 shows a photograph of ann iron oxide nanocrystal composite after 3 min placed next to a magnet. The solution was still homogeneous.
3 Figure S-4. Photograph showing ann iron oxide nanocrystal compositee after 3 min placedd next to a magnet. Figure S-5 shows the stability of the composite particles in different biochemically relevant media over time. Dulbecco'ss Modified Eagle's Medium (DMEM) containing media (DMEM and fetal calf serum (FCS) as well as DMEMM and 4-(2-hydroxyethyl)-1- piperazineethanesulfonic acid (HEPES)) and citrate buffer (ph = 3) ) affected small changes in the hydrodynamic diameter. FCS and bovine serum albuminn (BSA) affected a scattering of the signal (FCS( = 14 nm; BSA = nm). No N significant changes were observed in water, Dulbecco's Phosphate-Buffered Saline (DPBS), 2-(N- morpholino)ethanesulfonic acid (MES), and sodium chloride (NaCl). Figure S- shows s the stability of the composite particles in the presence of different d phh values after 2 minutes. The particles weree stable in ph-range of ph 3 to phh 12.
4 Figure S-5. DLS Data (intensity distribution) showing the stability test of the composite particles in different media (after: h =, 3 h =, 1 d =, 4 d = ).
5 1,,,4,2 ph=1 ph=2 ph=3 ph=4 ph=5 ph= ph=7 ph= ph=9 ph=1 ph=11 ph=12 ph=13 ph= d (nm) Figure S-. DLS Data (intensity distribution) showing the stability test of the composite particles in the presence of ph 1 to ph 14. Figure S-7 shows the stability of the unpolymerized clusters in different biochemically relevant media over time. Dulbecco's Modified Eagle's Medium (DMEM) containing media (DMEM and fetal calf serum (FCS) as well as DMEM and 4-(2-hydroxyethyl)-1- piperazineethanesulfonic acid (HEPES)) and citrate buffer (ph = 3) affected small changes in the hydrodynamic diameter. FCS and bovine serum albumin (BSA) affected a scattering of the signal (FCS = 14 nm; BSA = nm). The unpolymerized clusters show a slightly lower stability in water, citrate buffer (ph = 3) and NaCl solution. Figure S- shows the stability of the unpolymerized clusters in the presence of different ph values after 2 minutes. The particles were stable in ph-range of ph 3 to ph 12.
6 12 1 1,,,4 4,22 waterl ,,,44 2,2 DPBS d/nmd (nm) d/nm d (nm) ,,,4 4,2 2 citrate buffer (ph=3)l ,,,44 2,2 NaCl d/nm d/nm ,,,4 4,22 MESl ,,,44 2,2 DMEM + HEPES (1%) d/nm d (nm) d/nm d (nm) 12 1, 1,,4 4,2 2 DPBS + BSA (3%) ,,,44,22 DMEM + FCS d/nm d (nm) d/nm d (nm) Figure S-7. DLS Data (intensity distribution) showing the stability test of the unpolymerized clusters particles in different media (after: h =, 3 h =, 1 d =, 4 d = )
7 1,,,4,2 ph=1 ph=2 ph=3 ph=4 ph=5 ph= ph=7 ph= ph=9 ph=1 ph=11 ph=12 ph=13 ph= d (nm) Figure S-. DLS Data (intensity distribution) showing the stability test of the unpolymerized clusters in the presence of ph 1 to ph 14.
8 AFM measurement An AFM micrograph and height profile of the sample shownn in Figure 2 (d), as well as the corresponding histogram can be seen in Figure S-9. Figure S-9. a): AFM micrograph and b): height profile of the sample shown in Figure 2 (d), c): the corresponding histogram.
9 Functionalization of polysorbate e- A schematic illustration product (polysorbate- CH)) was showing the transformation off the terminal groups of polysorbate- can be seen in Figure S-1. Figure S-1. Schematic illustration showing transformation of the terminal groups of polysorbate-. Synthesis of carboxyl-terminated polysorbate- To 2. g polysorbate- (1.53( mmol) dissolvedd in 1 ml chloroform, 37.4 mg of the nucleophilic Steglich-Höflee catalyst, 4-dimethylaminopyridine, (3 µmol,.2 eq) were added. After addition of 74 mg succinic anhydride (7.3 mmol, 5 eq) dissolved in 3 ml chloroform, the reaction mixture was stirred for 4 hours h at room temperature. Subsequently, the solvent was evaporated, and the yellow, viscous pellet resuspended in a water and ethanol solution (1:1).. The raw dialyzed for two days and lyophilized.
10 Calculated conversion of the reaction by NMR: 75% referring H-groups. 1 H-NMR (5 MHz, CDCl 3 ): δ (ppm) =. (t, 3 H, 3 J Me, H-27 = 7.3 Hz, Me), (m, 2 H, CH and CH ), 1.2 (quin., 2 H, 3 J H-15, H-14 = 7. Hz, 3 J H-15, H-1 =.9 Hz, CH 2-15), 2. (q, 4 H, 3 J H, H =.3 Hz, CH ), 2.32 (t, 2 H, 3 J H-14, H-15 = 7. Hz, CH 2-14), 2.3 (m, H, per C CH 2 CH 2 CH), (m, 5, PE, CH 2-5 9), 4.22 (t, 2 H, CH 2-13, 3 J H, H = 5.2 Hz), 4.2 (m, 2 H, per CH 2 -C-CH 2 CH 2 CH), (m, 2 H, CH-2 29). 13 C-NMR (12 MHz, CDCl 3 ): δ (ppm) = 14. (Me), 24.9 (C-15), 27.1, (C-2 21), (C-1 19 and C-22 27), 31.9 (C CH 2 CH 2 CH), 34.2 (C-14), 3.3 (C-1), 3.1 (C-13), 9.1, 9.2, 7.52 (PEG and C-5 9), , 13. (C-2 and C-29). H w 5 7 H x 9 1 y z 13 H Me Synthesis of aldehyde-terminated polysorbate-
11 Dess-Martin periodinane (1.1 g, mol, 1.2 eq.) was dissolved in 5 ml dichlormethane. To this solution, 1. g ( mol) of polysorbate- in 1 ml dichloromethane was added. The reaction mixture was stirred for 4 h. The precipitate was removed by centrifugation and the supernatant was evaporated. The remaining residue was dissolved in 1 ml dichlormethane and precipitated by addition of cold diethyl ether. The product (polysorbate--ch) was dissolved in water and lyophilized. Calculated conversion of the reaction by NMR: 2% referring H-groups. 1 H-NMR (5 MHz, CDCl 3 ): δ (ppm) =. (t, 3 H, 3 J Me, H-27 = 7.3 Hz, Me), (m, 2 H, CH and CH ), 1.2 (quin., 2 H, 3 J H-15, H-14 = 7. Hz, 3 J H-15, H-1 =.9 Hz, CH 2-15), 2. (q, 4 H, 3 J H, H =.3 Hz, CH ), 2.32 (t, 2 H, 3 J H-14, H-15 = 7. Hz,CH 2-14), (m, 5, PE, CH 2-5 9), 4.15 (m, 2 H, CH 2 CH), 4.2 (t, 2 H, 3 J H, H = 5.2 Hz, CH 2-13), (m, 2 H, CH-2 29), 9.72 (s, 1 H, CH). 13 C-NMR (12 MHz, CDCl 3 ): δ (ppm) = 14. (Me), 22.4 (C-27), 24. (C15), 27.15, 27.2, (C-2, C-21), (C-1 19, C-22 25), 31.7 (C-2), 34.1 (C-14), 3.33 (C-13), (PE, C-5 9), 7.4 (CH 2 CH), , (C-2, C-29), 173. (CR), 19. (CH).
12 Implementation of an alkyne-terminated polysorbate- To g (45.2 mmol) 1,1 -carbonyldiimidazole (CDI) ( eq.) dissolved in 1 ml dichlormethane, 1. g ( mol) polysorbate- dissolved in 1 ml dichloromethane was added. After stirring for 4 h, the organic solution was washed three times with water to hydrolyze the excess CDI. The organic phase was dried with sodium sulfate, and concentrated to a volume of 2 ml. To the imidazole-activated polysorbate-, 1.22 g (22.91 mmol), propargylamine was added and the mixture stirred for 4 h at 55 C. The crude product (polysorbate- C CH) was precipitated three times from cold acetone, dissolved in water and then lyophilized. Calculated conversion of the reaction by NMR: 5% referring H-groups. 1 H-NMR (5 MHz, CDCl 3 ): δ (ppm) =. (t, 3 H, 3 J Me, H-27 = 7.3 Hz, Me), (m, 2 H, CH and CH ), 1.2 (quin., 2 H, 3 J H-15, H-14 = 7. Hz, 3 J H-15, H-1 =.9 Hz, CH 2-15), 2. (q, 4 H, 3 J H, H =.3 Hz, CH ), (m, 1 H, perc CH ), 2.32 (t, 2 H, 3 J H-14, H- 15 = 7. Hz, CH 2-14), (m, 5, PE, CH 2-5 9), (m, 2 H, per CH 2 -C CH), 4.22 (t, 2 H, 3 J H, H = 5.2 Hz, CH 2-13), (m, 2 H, CH-2 29). 13 C-NMR (12 MHz, CDCl 3 ):
13 δ (ppm) = (C-2 21), (C-1 19 and C-22 27), 2.43 (C-13), (PE and C-5 9), , 129. (C-2 and C-29).
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