Fabrication of Bio-based Polyelectrolyte Capsules and Their Application for Glucose-Triggered Insulin Delivery

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1 Supporting Information for Fabrication of Bio-based Polyelectrolyte Capsules and Their Application for Glucose-Triggered Insulin Delivery Dongjian Shi a*, Maoshuang Ran a, Li Zhang a, He Huang a, Xiaojie Li a, Mingqing Chen a*, Mitsuru Akashi b a The Key Laboratory of Food Colloids and Biotechnology Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi , P. R. China b Department of Applied Chemistry, Graduate School of Engineering, saka University, 2-1 Yamadaoka, Suita , Japan Author to whom correspondence should be addressed; mqchen@jiangnan.edu.cn, djshi@jiangnan.edu.cn Tel.: ; Fax: S-1

2 FTIR spectra of chitosan (Figure S1a) and Galactose modified chitosan oligosaccharide (GC) (Figure S1b) were shown in Figure S1. Characteristic absorptions bands (cm -1 ) at 3264 (N-H stretch), 2883 (C-H stretch), 1633 (amide I band), 1572 (amide II band), 1151 (C--C anti-symmetric stretch), and 1031 (C- stretch) were found to assigned to the chitosan oligosaccharide. After introducing LA, all peaks of amides I and II of GC shifted from 1633 cm -1 and 1572 cm -1 to 1615 cm -1 and 1516 cm -1, respectively. Moreover, the N-H stretching peak of GC appeared at around 3264 cm -1 became slightly weaken, indicating that the amine groups of chitosan oligosaccharide and carboxyl groups of LA reacted to amide bond. FTIR results confirmed that LA successfully grafted into the CS chains. HH 2 C H NH 2 n HH 2 C H HH 2 C NH 2 n-y NH y H C HH 2 C H C H H H C H C H H H H C H CH 2 H Wavenumber (cm -1 ) Figure S1. FTIR spectra of chitosan oligosaccharide and galactosed chitosan oligosaccharide. Figure S2 shows the FTIR spectra of APBA (Figure S2a), γ-pga (Figure S2b) and γ-pga-g-apba (Figure S2c-e). The characteristic absorptions bands (cm -1 ) of γ-pga S-2

3 was as follows: 3400 (-H stretch), 2998 (C-H stretch), 1726 (C= stretch), 1532 (N-H plane bend), 1215 (C-N stretch), and 765 (N-H out-of-plane bend). From FTIR spectrum of γ-pga-g-apba (Figure S2c-e), three new peaks had been found at 1640 cm -1, 795 cm -1 and 703 cm -1, which belonged to the amide bond and benzene ring, respectively. These results indicating APBA reacted with γ-pga. (e) (d) (c) Wavenumber (cm -1 ) Figure S2. FTIR spectra of APBA, γ-pga, γ-pga-g-apba 0.12 (c), γ-pga-g-apba 0.29 (d) and γ-pga-g-apba 0.40 (e). Table S1. Synthesis and characterization of γ-pga-g-apba Samples. γ-pga/apba/edc/nhs (mmol) Graft ratio Zeta potential (%) a (mv) b γ-pga-g-apba /1.5/1.5/4.5 12% ±0.15 γ-pga-g-apba /3/3/9 29% ±0.15 γ-pga-g-apba /4.5/4.5/ % ±0.15 a Graft ratio was determined by 1 H-NMR; b Zeta potential was obtained from Zeta PALS at ph 5. S-3

4 Si 2 (γ-pga-g-apba/gc) 2 ((γ-pga-g-apba/gc) 5 ) capsules Diameter (nm) Figure S3. Dynamic light scattering (DLS) of the Si 2 nanoparticles, (γ-pga-g- APBA/GC) 2 nanoparticles and (γ-pga-g-apba/gc) 5 capsules. (c) Diameter (nm) Figure S4. TEM and SEM images and DLS (c) curve of (γ-pga-g-apba/gc) 5 capsules after freeze-drying process. S-4

5 Figure S5. Morphologies of the (γ-pga-g-apba 0.29 /GC) 5 (a-c) and (γ-pga-g-apba 0.40 /GC) 5 (d-f) capsules with time at 20 mg/ml of glucose solution Particle size (nm) mg ml -1 2 Particle size (nm) mg ml -1 6 mg ml Time (h) Time (h) Figure S6. Glucose sensitivity of the (γ-pga/cs) 5 and (γ-pga-g-apba 0.29 /CS) 5 capsules in PBS solution (ph 7.4) with different glucose levels at 37 C. S-5

6 y = 0.981x R² = Concentration of insulin (mg/ml) Figure S7. Insulin calibration curve generated by spectrophotometer at 595 nm from a series of insulin w different concentrations using coomassie brilliant blue (G-250) as visual indicator Cumulative release (%) on-off Time (h) Figure S8. Insulin cumulative release from the (γ-pga-g-apba 0.29 /CS) 5 capsules in PBS triggered by alternant glucose concentrations at 20-0 mg/ml. S-6

7 (c) Wavelength (nm) Figure S9. Circular dichroism (CD) spectra of the native insulin in PBS at ph 7.4 and at ph 5.5 and insulin released after 12 h from the capsules (c). Figure S10. Inverted microscope images of the (γ-pga-g-apba 0.12 /GC) 5, (γ-pga-g-apba 0.29 /GC) 5 and (γ-pga-g-apba 0.40 /GC) 5 (c) capsules after incubation for 24 h at 37 o C. S-7

Supplementary Information for: Label-free Monitoring of the Nanoparticle Surface. Modification Effects on Cellular Uptake,

Electronic Supplementary Material (ESI) for Toxicology Research. This journal is The Royal Society of Chemistry 2014 Supplementary Information for: Label-free Monitoring of the Nanoparticle Surface Modification