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1 Supporting Information Cancer Cell Membrane-Biomimetic Nanoprobes with Two-Photon Excitation and Near-Infrared Emission for Intravital Tumor Fluorescence Imaging Yanlin Lv 1,2,, Ming Liu 3,4,, Yong Zhang 3 *, Xuefei Wang 1, Fan Zhang 2, Feng Li 2, Wei-Er Bao 2, Jie Wang 1, Yuanlin Zhang 1, Wei Wei 2 *, Guanghui Ma 2 *, Liancheng Zhao 3, Zhiyuan Tian 1 * 1 School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 149, P. R. China. 2 State Key Laboratory of Biochemical Engineering, Institute of Process Engineering, CAS Beijing 119, P. R. China. 3 School of Materials Science and Engineering, Harbin Institute of Technology, Harbin 151, P. R. China. 4 School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 4352, P. R. China. Yanlin Lv and Ming Liu contributed to this work equially. 1

2 CD44 3% 4% 55% Figure S1. Photograph of the protein bands after the density gradient centrifugation and the Dot-blot result of protein along the gradient. 2

3 Figure S2. Zeta potential results of hybrid NPs, hybrid NPs after surface charge inversion (hybrid NPs (+)) and the target M-NPs nanoprobes. Results were expressed as means ± s.d. (n = 3). The aqueous dispersion sample containing hybrid NPs reported a zeta potential of approximately 21.3 mv, indicating their negatively charged surface. To facilitate the encapsulation of these hybrid NPs into tumor cell membrane characterized with negative surface charge, a P-L-lysine modification of the NPs for surface charge reversal was conducted, yielding the hybrid NPs (+) with zeta potential of mv. Upon further cancer cell membrane encapsulation, the resultant nanoprobes displayed zeta potential of -1.1mV. Such change in surface charge, together with the changes in DLS and TEM characterization results, definitely confirmed the cloak of cell membrane around the original hybrid NPs. 3

4 A Number (%) Hybrid NPs B Number (%) M-NPs Size (nm) Size (nm) Figure S3. Dynamic light scattering (DLS) characterization of the hybrid NPs (A) and M-NPs (B). The dynamic light scattering characterization of the hybrid NPs displayed an average hydrodynamic radius of ~155 nm with a relatively narrow polydispersity (A). Upon cancer cell membrane encapsulation, the resultant nanoprobes aqueous dispersion sample displayed a hydrodynamic radius of ~19 nm (B). Such change in average hydrodynamic radius, together with the change in surface charge and TEM characterization results, definitely confirmed the cloak of cell membrane around the original hybrid NPs. 4

5 Size (nm) M-NPs Hybrid NPs Time (day) Figure S4. Evolution of the average hydrodynamic radius of the hybrid NPs and M-NPs upon storage with time up to 3 d. Results were expressed as means ± s.d. (n = 3). 5

6 Flu. Int. (a.u.) 25 day day 1 2 day 2 day 4 15 day 7 day 1 1 day 15 day 2 5 day 25 day Wavelength (nm) Figure S5. Evolution of the fluorescence emission feature of the M-NPs upon storage with time up to 3 d. 6

7 Counts (x1 4 ) 6. M-NPs 5. Hybrid NPs NPs Time (s) Figure S6. Evolution of fluorescence intensity (at 72 nm) of hybrid NPs and M-NPs upon continuous irradiation of 388-nm laser with time up to 3 min. Similar to two-photon excitation, both the hybrid NPs and M-NPs exerted excellent anti-photobleaching ability. The 3-min continuous irradiation only caused the NIR fluorescence of hybrid NPs and M-NPs decreasing for 16.1% and 8.4%, respectively. In addition, the difference value of 7.7% between hybrid NPs and M-NPs reflected the positive role of CM cloaking to the fluorescence intensity. 7

8 Cell Viability (%) 12 M-NPs 1 Hybrid NPs Concentratin (µg/ml) Figure S7. Cell viability of HeLa cells incubated with hybrid NPs and HeLa M-NPs nanoprobes at various concentrations with incubation time up to 24 h. Results were expressed as means ± s.d. (n = 3). Although the cell viability displayed slightly decrease upon increasing the concentration of hybrid NPs and M-NPs nanoprobes, more than 81% and 86% cells still survived in the case of cells incubation with the hybrid NPs and M-NPs nanoprobes, respectively, with concentration up to 2 µg/ml for 24 h. Thus, the M-NPs nanoprobes developed herein possess good biocompatibility for biological applications. 8

9 A i ii B iii iv M-NPs Nucleus Membrane Figure S8. Evaluation of targeting specificity of the M-NPs probes to various cell lines. (A) CLSM images of NIH 3T3 cells (i), 4T1 cells (ii), J774 cells (iii) and HeLa cells (iv) after incubation with HeLa M-NPs. Scale bar was 1 µm. (B) Flow cytometry analysis of various cells after incubation with HeLa M-NPs. Specifically, considerable amount of M-NPs were internalized in HeLa cells after incubation. In sharp contrast, no noticeable HeLa M-NPs were found in other types of cells under identical incubation condition. Such disparity again supplemented the targeting specificity of HeLa M-NPs to homologous HeLa cells. 9

10 A i ii B C 18 i ii 25 CD (mdeg) BSA BSA+L Wavelength (nm) Figure S9. Targeting ability of M-NPs after illumination of 8-nm pulse laser. (A) The IR images of M-NPs before (i) and after (ii) illumination. (B) Circular dichroism (CD) spectra of Bovine Serum Albumin (BSA) in phosphate buffer (PB) before and after illumination. (C) CLSM images of HeLa cells after incubation with HeLa M-NPs without (i) and with (ii) illumination. The temperature of the M-NPs sample increased from 22.7 to 23.5 C upon 3-min illumination. Under this moderate condition, the structure of membrane protein remained unchanged, and BSA was chosen as the model protein. Therefore, the tumor targeting ability of M-NPs was maintained upon 3-min illumination of an 8-nm pulse laser. 1

11 Relative Flu. (%) Bare NPs hybrid NPs M-NPs Time (h) Figure S1. Time-dependent fluorescence intensity of polymeric NPs without modification of DSPE-mPEG 2 (bare NPs), DSPE-mPEG 2 enveloped NPs (hybrid NPs) and cell membrane-coated M-NPs after intravenous administration. Results were expressed as means ± s.d. (n = 3). The bare NPs displayed relatively short circulation time with half-time less than 1 h, which could be significantly ameliorated in hybrid NPs group. Once cancer cell membrane was coated (M-NPs), the circulation time could be further improved. Such a talent was beneficial to tumor accumulation and subsequent imaging. 11

12 A i ii iii 2 *** B Flu. Int. (%) ** * Hybrid NPs FA-NPs M-NPs Hybrid NPs FA-NPs M-NPs Figure S11. Evaluation of the targeting ability of hybrid NPs, FA-NPs and M-NPs to HeLa cells. (A) CLSM images of HeLa cells after incubation with hybrid NPs (i), FA-NPs (ii) and HeLa M-NPs (iii) for 2 h. Scale bar was 2 µm. The cell membrane (green) and nucleus (blue) were stained by Alexa Fluor 488 phalloidin and Hoechst 33342, respectively. (B) Flow cytometry analysis of HeLa cells after incubation with various NPs. Results were expressed as means ± s.d. (n = 3) *p <.5, **p <.1, ***p <.1, analyzed by one-way ANOVA. M-NPs invaded HeLa cells more than FA-NPs, demonstrated the superior high targeting efficiency of homologous target. The quantitive analysis of FCM showed FA-NPs group enhanced ~1.5-fold while M-NPs group increased ~16-fold in the intracellular fluorescence intensity, compared with hybrid NPs group. Thus, the active target greatly promoted the targeting efficiency, and the targeting ability of M-NPs was superior to FA-NPs. 12

13 A 6-78 nm 46-6 nm % Flu. Int. (a.u.) 5 ** 62.3% B 1 µm 3 µm ** µm 3 µm 6-78 nm 46-6 nm Flu. Int. (a.u.) 5 58.% *** 8.7% µm 3 µm µm 3 µm Figure S12. The penetration ability assessment of TPE and SPE in 2D HeLa cells by collecting different waveband of emission. (A) Typical TPEF fluorescence images acquired with 8-nm laser crossing -µm-thick and 3-µm-thick mock tissue and capturing photons in NIR region (left panel) and visible region (middle panel), respectively, and the comparison of corresponding fluorescence intensity (right panel). (B) Typical SPEF fluorescence images acquired with 45-nm laser crossing -µm-thick and 3-µm-thick mock tissue and capturing NIR photons in region (left panel) and visible region (middle panel), respectively, and the comparison of corresponding fluorescence intensity (right panel). Scale bar was 5 µm. Results were expressed as means ± s.d. (n = 3) *p <.5, **p <.1, ***p <.1, analyzed by one-way ANOVA. In the TPE-based NIR-incoming-NIR-outgoing imaging mode (Ex 13

14 = 8 nm, Em = 6-78 nm), a 3-µm-thick mock tissue brought out only ~1% decrease in beaconing fluorescence signal intensity (images with red signal in Figure S8A). In contrast, mock tissue with the same thickness in the case of TPE-based imaging via capturing photon in the visible region (Ex = 8 nm, Em = 46-6 nm) resulted in decrease in fluorescence intensity with loss percentage up to ~62% (images with green signal Figure S8A). In sharp contrast, in the counterpart imaging modes based on single-photon excitation (Ex = 45 nm), a 3-µm-thick mock tissue resulted in attenuation of ~58% NIR fluorescence signal intensity (Em = 6-78 nm) and marked decrease in green fluorescence intensity with loss percentage up to ~81% (Em = 46-6 nm). Unequivocally, for mapping intravital deep-seated target, our probes with NIR-incoming-NIR-outgoing feature have overwhelming superiority in terms of circumventing the attenuating effects of absorption and light scattering caused by optically turbid tissues. 14

15 A B Figure S13. The TPE-based fluorescence images of 3D multicellular tumor spheroid (MCTS) model after incubation with M-NPs (A) and hybrid NPs (B). Scale bar was 1 µm. Obviously, the M-NPs displayed much better permeability than that of the hybrid NPs, which can be attributed to the active homologous membrane interactions of the former. 15

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