General and Facile Surface Functionalization of Hydrophobic Nanocrystals with Poly(amino acid) for Cell Luminescence Imaging

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1 General and Facile Surface Functionalization of Hydrophobic Nanocrystals with Poly(amino acid) for Cell Luminescence Imaging Sheng Huang, Min Bai, Leyu Wang* State Key Laboratory of Chemical Resource Engineering, School of Science, Beijing University of Chemical Technology, Beijing , China

2 Supporting information Cytotoxicity assay. Briefly, HeLa cells ( cells/well) attached to the bottom of the 96-well cell culture plate were incubated with different amounts (0 300 µg/ml) of sterilized NaYF 4 :Yb 3+ /Er OAm -COO - NPs or ZnS:Mn OAm -COO - NPs in each well at 37 C for 24 or 48 h, respectively. Thereafter, the cytotoxicity was evaluated via the methyl thiazolyltetrazolium (MTT) assay. 1-2 Bioconjugation with folic acid (FA). 1 ml DMSO solution containing 5 mg of FA and 1 ml PBS (ph=7.4, 0.1 M) containing 20 mg of EDC and 12 mg of NHS were mixed with 1 ml hydrophilic nanomaterials, followed by incubating at 25 C for 4 h. Finally, the FA-nanomaterial bioconjugates were collected by centrifugation (11000 rpm, 10 min) and washed with PBS, and this purification process was repeated for three times. The obtained FA conjugated nanomaterial bioconjugates were redispersed in PBS (ph = 7.4, 3 ml) and stocked at 4 C for later use. Cell imaging. HeLa cells were seeded on a sterilized glass cover slide and cultured in a 12-well cell culture plate overnight under recommended conditions at 37 C in 5% CO 2 humidified incubator. Then the folic acid (FA) bioconjugated nanomaterial stock solution was added into the cell culture well with a final concentration of 100 μg/ml. The HeLa cells were incubated with nanomaterials for another 4 h. As a control, the bare nanomaterials without FA in place of nanomaterials conjugated with FA, were incubated with the HeLa cells under the same conditions. Thereafter, the cells on the glass slide were washed with phosphate buffer solution (PBS, ph 7.4, 10 mm) and fixed in 4% paraformaldehyde solution for 15 min. The luminescence imaging was conducted on a TCS SP5 two-photon confocal microscopes (Leica) equipped with a Mai Tai near infrared (NIR) diode laser. Preparation and collection of hydrophobic nanocrystals used in this work The nanocrystals used in this work were prepared according to the reported methods with minor revision. All the as-prepared nanocrystals were collected by centrifugation,

3 washed with cyclohexane and ethanol for several times, and finally redispersed into chloroform for later use. Synthesis of Ag nanocrystals. 3 5 ml of aqueous solution containing 0.2 g of NaOH was mixed with 15 ml of ethanol, 3 ml of oleic acid, 1 ml of oleylamine and 3 ml of cyclohexane. Subsequently, 5 ml of AgNO 3 aqueous solution containing 0.25g of AgNO 3 and 10 ml of ethanol were added under stirring. The mixture was then transferred into a 40-mL Teflon-lined vessel, sealed in an autoclave, and then treated at 100 C for 10 h. Synthesis of ZnS:Mn 2+ nanocrystals ml of aqueous solution containing 0.6 g of NaOH were mixed with 8 ml of ethanol and 10 ml of oleic acid. Subsequently, 1.9 ml of aqueous solution of ZnCl 2 (1.0 M), 0.1 ml of aqueous solution of MnCl 2 4H 2 O (0.1 M) and 2.2 ml of aqueous solution of Na 2 S (1.0 M) were added under stirring. Then the colloidal solution was transferred into a 40-mL Teflon-lined autoclave and heated at 160 ºC for 8 h. Synthesis of Fe 3 O 4 nanocrystals. 4 Firstly, the iron oleate complex was prepared beforehand. In brief, 4.8 ml aqueous solution containing g of NaOH were mixed with 6.4 ml of ethanol. Then 3 ml of oleic acid and 11.2 ml of cyclohexane were added, followed by the addition of 3 ml aqueous solution containing g of FeCl 3 6H 2 O. The resulting solution was heated to 70 C and kept at that temperature for 4 h. Thereafter, the upper organic layer containing the iron oleate complex was washed three times with 30 ml deionized water in a separatory funnel. After the evaporation of cyclohexane, the waxy iron oleate complex was obtained. Secondly, the obtained iron-oleate (2.88g) was dissolved in 20 ml of 1-octadecene at room temperature and then heated to 310 C and kept at this temperature for 30 min to get the magnetite NPs. Synthesis of LaF 3 :Ce 3+ /Tb 3+ nanocrystals ml of aqueous solution containing 0.4 g of NaOH was mixed with 10 ml of ethanol and 10 ml of oleic acid. Then, 1.0 ml aqueous solution of Ln(NO 3 ) 3 (La/Ce/Tb= 90/5/5, 0.5 M for total Ln), 4 ml aqueous solution of NaF (1 M) and 10 ml of ethanol were added successively under stirring. The mixture was

4 then transferred into a 40-mL Teflon-lined vessel, sealed in an autoclave, and then treated at 190 C for 12 h. Synthesis of NaYF 4 :Yb 3+ -Er 3+ nanoparticles. 1-2 To synthesize the β-phase NaYF4:Yb 3+ -Er 3+ nanoparticles, a mixture of 8 ml of oleic acid, 7 ml of octadecene, and 0.35 g of sodium stearate were added into a three-necked flask and stirred thoroughly. Then, 3 ml of the as-prepared rare-earth oleate solution and 1.05 ml of the HF oleylamine solution were quickly injected into the flask and kept at 80 C for 20 min. Then, the solution was heated to 180 C for 10 min before it was heated to 310 C for 1 h. The mixture solution was kept under a protective nitrogen flow throughout. The reaction solution was cooled to room temperature, and the product was collected by centrifugation. The as-prepared nanorods were redispersed into cyclohexane and precipitated by addition of ethanol for further purification. The final product was redispersed in 5 ml of chloroform and stored for later use. Synthesis of NaYF 4 :Yb 3+ /Er 3+ nanorods (nanoparticles). 1 Note please, the data in parentheses are for the synthesis of nanoparticles. 6 (7) ml of oleic acid, 9 (8) ml of octadecene and 0.35 g of sodium stearate were added into a three-necked flask and stirred thoroughly. Then 4 (4) ml of the as-prepared rare-earth oleate solution and 1.6 (1.4) ml of the HF oleylamine solution were quickly injected into the flask and kept at 80 C for 20 minutes. Then the solution was treated at 180 C for 10 minutes before it was heated to and kept at 310 C for 1 hour. The mixture solution was kept under a protective nitrogen flow throughout. Synthesis of YPO 4 nanoplates ml of aqueous solution containing 0.4 g of NaOH was mixed with 10 ml of ethanol and 10 ml of oleic acid. After a while, 5.0 ml aqueous solution of NaH 2 PO 4 (0.2 M), 5.0 ml aqueous solution of Y(NO 3 ) 3 (0.2 M) and 10 ml of ethanol were added step by step. The mixture was then transferred into a 40-mL Teflon-lined vessel, sealed in an autoclave, and then treated at 140 C for 8 h.

5 Figure S1. Synthesis of the PSIOAm and PSIOAm-COO from PSI. OAm: oleylamine; PSIOAm: oleylamine-modified poly succinimide; PSIOAm-COO : PSIOAm with carboxylic groups after hydrolyzation. Figure S2. NPs stabilized by amphiphilic poly-(amino acid) through hydrophobic interaction.

6 Figure S3. TEM images (1, 2) and digital photograph (3, 4) of inorganic nanocrystals before (1, 3) and after (2, 4) surface modification. a) NaYF4:Yb3+/Er3+ nanorods, b) YPO4 nanoplates; Photographs (3, 4): the top layer is water and the bottom is chloroform; a3 and a4) 980 nm diode laser; b3 and b4) day light; Scale bar: 100 nm Linear Spec #1 MC[BP = , 101] % Intensity Mass (m/z) Figure S4. Mass spectroscopy of the as-prepared poly(amino acid). Molecular weight (Mw) of PSI OAm -COOH (after aminolysis and hydrolysis) was 7958, which was determined by a 4800 Plus MALDI TOF/TOF mass spectrometer. 1. Deng, M. L.; Ma, Y. X.; Huang, S.; Hu, G. F.; Wang, L. Y., Monodisperse upconversion NaYF 4 nanocrystals: Syntheses and bioapplications. Nano Res. 4, (2011). 2. Deng, M. L.; Tu, N. N.; Bai, F.; Wang, L. Y., Surface Functionalization of Hydrophobic Nanocrystals with One Particle per Micelle for Bioapplications. Chem. Mat. 24, (2012). 3. Wang, X.; Zhuang, J.; Peng, Q.; Li, Y. D., A general strategy for nanocrystal synthesis. Nature 437, (2005).

7 4. Park, J.; An, K. J.; Hwang, Y. S.; Park, J. G.; Noh, H. J.; Kim, J. Y.; Park, J. H.; Hwang, N. M.; Hyeon, T., Ultra-large-scale syntheses of monodisperse nanocrystals. Nat. Mater. 3, (2004).

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