Self-assembled ZnO nanoparticle capsules for carrying and delivering isotretinoin to cancer cells

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1 Supporting Information Self-assembled ZnO nanoparticle capsules for carrying and delivering isotretinoin to cancer cells Wei Zhao, Ji-Shi Wei, Peng Zhang, Jie Chen, Ji-Lie Kong,,, * Lian-Hua Sun, Huan-Ming Xiong, * and Helmuth Möhwald Department of Chemistry and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai , P. R. China. Institutes of Biomedical Sciences, Fudan University, Shanghai , P. R. China. Ear Institute, Shanghai Jiaotong University School of Medicine, Shanghai , P. R. China. Max-Planck Institute of Colloids and Interfaces, Potsdam 14424, Germany. * jlkong@fudan.edu.cn; hmxiong@fudan.edu.cn S-1

2 To find the optimal loading capacity, we used different feeding ratios to synthesize ZnO-ISO, then we used DLS and TEM techniques for structure characterization. According to Figure S1, S2 and S4, as the ISO ratio increases, the obtained ZnO-ISO grows larger and larger. 1:0.5 is the optimal ratio, because beyond this ratio the nanoparticles will aggregate and precipitate. At this feeding ratio, the loading capacity is 34.6 wt.%. Figure S1 Dynamic light scattering (DLS) data of the ZnO-ISO spheres prepared by different weight ratios. Figure S2 TEM images of ZnO-ISO composites with the weight ratio of (A) 1:0.1 and (B) 1:0.3. S-2

3 We added excessive ZnO NPs into the ZnO-ISO solution and took a TEM image as below. Obviously the excess ZnO NPs are not coating on ISO, but they are much darker and smaller than ZnO-ISO spheres. Figure S3 HRTEM of ZnO-ISO nanocapsules with excess ZnO nanoparticles. Figure S4 Particle size distributions of the ZnO-ISO composites with feeding weight ratios of (A) 1:0.1, (B) 1:0.2, (C) 1:0.3 and (D) 1:0.5. S-3

4 Figure S5 Energy Dispersive X-ray (EDX) spectrum of the ZnO-ISO composite. Figure S6 UV-Vis (A) spectra and DLS (B) of the newly synthesized ZnO-ISO and the sample synthesized one year ago. Both Nintedanib and Crizotinib are soluble in water, while ISO is insoluble in water. When Nintedanib and Crizotinib are loaded onto ZnO NPs respectively, both drugs are only adsorbed on ZnO NP surfaces. Such absorption effects are very weak, and thus the loading capacities of both Nintedanib and Crizotinib are very low. In contrast, ISO is insoluble in water. When its DMSO solution is dropped into water, ISO will aggregate and precipitate. However, when its DMSO solution is dropped into the ZnO NPs aqueous solution, the ZnO NPs will coat the ISO agglomerates to form stable core-shell structure. We also tried different ratios in the preparation of ZnO-Nintedanib and ZnO-Crizotinib, respectively. See the table below. It is clear, that increasing the feeding ratio to some extent, the loading capacity of both drugs on S-4

5 ZnO NPs surfaces cannot be increased together. Excess drugs will be dialyzed out through the dialysis bags, because both drugs are soluble in water. Feeding weight ratio (ZnO : drug) 1:0.05 1:0.08 1:0.1 1:0.2 1:0.3 1:0.5 Load capacity for Nintedanib (weight percent) 3.4% 6.8% 7.4% 7.3% 7.4% 7.5% Load capacity for Crizotinib (weight percent) 2.7% 5.3% 6.9% 6.8% 6.8% 7.0% Table S1 Feeding ratios of ZnO and drugs, and the resulting loading capacities. Figure S7 Cell viability for 6 kinds of cells (A) DU145, (B) MCF-7, (C) HeLa, (D) A549, (E) DLD-1, (F) HepG-2, cultivated with ZnO-ISO for different doubling time. The ISO concentration for each MTT assay is 5 µg/ml. S-5

6 Median IC50 ± Standard Deviation (µg/ml) DU145 ISO 16.38±0.23 ZnO-ISO 5.44±0.64 HeLa MCF-7 A549 HepG-2 DLD ± ± ± ± ± ± ± ± ± ±0.12 Table S2 IC50 (µg/ml) for different cells after 24 hours incubation with ZnO-ISO and ISO, respectively. All concentrations are the ISO concentrations. Figure S8 UV-Vis absorption of (A) Pure Crizotinib, ZnO NPs and ZnO-Crizotinib, and (B) Pure Nintedanib, ZnO NPs and ZnO-Nintedanib. Figure S9 TEM images of (A) ZnO-Crizotinib and (B) ZnO-Nintedanib. S-6

7 Figure S10 Cytotoxicity toward tumor cells A549 from (A) ZnO-Crizotinib, ZnO and Crizotinib, and (B) ZnO-Nintedanib, ZnO and Nintedanib in different concentrations. Scheme S1 Two different formation processes of the ZnO-ISO, and ZnO-Crizotinib or ZnO-Nintedanib nanoparticles. S-7

8 Figure S11 UV-Vis spectra of ZnO-ISO, IR780 and ZnO-ISO-IR780. We conducted the following experiments to investigate the cell uptake of ZnO-ISO. Firstly, about 10 5 cells were cultured with diluted ZnO-ISO NPs in DMEM for different time. Then, the cells and the cell culture medium were separated by centrifugation to measure the concentrations of Zn 2+ in each sample. The Zn 2+ concentrations were measured by ICP techniques after decomposing the samples with HCl solutions. Finally, we get the uptake rate of ZnO NPs by the following formula and calculate the corresponding uptake rate of ZnO-ISO. See Figure S12. Figure S12 Uptake fraction of ZnO-ISO by A549 cells at different doubling time. S-8

9 As we mentioned in the manuscript, retinoic acids, as natural derivatives of vitamin A, play important roles in cell differentiation, growth and apoptosis. ISO is one of the metabolized products from retinoic acids, which exhibits special immunomodulatory and anti-inflammatory responses. However, anticancer effects of ISO toward many cancers are not ideal, probably due to its insolubility in water. [1] In the early 1980s, [2] beta-carotene and retinoids were the most promising agents against common cancers when the National Cancer Institute established a substantial program of population-based trials. Since then, the study about isotretinoin for cancer therapy has already arisen lots of attention, and some of them concern clinical applications. In the processes of cancer prevention, leukoplakia, actinic keratosis, and cervical dysplasia are the three precancerous lesions that can be effectively treated by isotretinoin. [3, 4] In the process of killing cancer cells, isotretinoin induces radioiodine avidity of follicular thyroid cancer cells to accumulate radioiodine. There are also other researches concerning isotretinoin in medical treatments. [5-7] According to those previous researches, the mechanism of the ISO release is supposed to be that, ISO combines RXR specially in the tumor cells and then enters nucleus to down regulate the corresponding genes, which renders the cell apoptosis finally. Reference: [1] Bushue, N.; Wan, Y. J. Retinoid Pathway and Cancer Therapeutics. Adv. Drug Delivery Rev. 2010, 62, [2] Day, N. E.; Bingham, S. A. Nutrition Intervention Trials in Linxian, China: Supplementation with Specific Vitamin/Mineral Combinations, Cancer Incidence, and Disease Specific Mortality in the General Population. J. Natl. Cancer Inst. 1994, 86, [3] Lippman, S. M.; Sudbø, J.; Hong, W. K. Oral Cancer Prevention and the Evolution of Molecular-Targeted Drug Development. J. Clin. Oncol. 2005, 23, [4] Mao, L.; Papadimitrakopoulou, V.; Shin, D. M.; Fan, Y.; Zhou, X.; Lee, J. S.; Hong, W. K.; El-Naggar, A. K.; Shin, H. C.; Clayman, G.; Lee, J. J.; Hittelman, W. N.; Lippman, S. M. Phenotype and Genotype of Advanced Premalignant Head and Neck Lesions after Chemopreventive Therapy. J. Natl. Cancer Inst. 1998, 90, [5] Brtko, J. Retinoids, Rexinoids and Their Cognate Nuclear Receptors: Character S-9

10 and Their Role in Chemoprevention of Selected Malignant Diseases. Biomed. Pap. 2007, 151, [6] Matthay, K. K.; Reynolds, C. P.; Seeger, R. C.; Shimada, H.; Adkins, E. S.; Haas-Kogan, D.; Gerbing, R. B.; London, W. B.; Villablanca, J. G. Long-Term Results for Children With High-Risk Neuroblastoma Treated on a Randomized Trial of Myeloablative Therapy Followed by 13-cis-Retinoic Acid: A Children's Oncology Group Study. J. Clin. Oncol. 2009, 27, [7] Huang, S.; Laoukili, J.; Epping, M. T.; Koster, J.; Holzel, M.; Westerman, B. A.; Nijkamp, W.; Hata, A.; Asgharzadeh, S.; Seeger, R. C.; Versteeg, R.; Beijersbergen, R. L.; Bernards, R. ZNF423 is Critically Required for Retinoic Acid-Induced Differentiation and is a Marker of Neuroblastoma Outcome. Cancer Cell 2009, 15, S-9

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