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1 Supporting Information Mitochondria-Targeting Polydopamine Nanocomposites as Chemophotothermal Therapeutics for Cancer Zhuo Wang *,, Yuzhi Chen, Hui Zhang, Yawen Li, Yufan Ma, Jia Huang, Xiaolei Liu, Fang Liu, Tongxin Wang, *, Xin Zhang *, State Key Laboratory of Chemical Resource Engineering, Beijing Advanced Innovation Center for Soft Matter Science and Engineering, College of Science, Beijing University of Chemical Technology, Beijing , China College of Engineering and College of Dentistry, Howard University, Washington, DC 20059, United States Department of Hepatobiliary Surgery, Department of Gastroenterology, China-Japan Friendship Hospital, Beijing , China Corresponding Auther: * wangzhuo77@mail.buct.edu.cn; zhangxin@mail.buct.edu.cn; twang@howard.edu. 1. Table S1. Binding energies of Dox, Rhod123 and PDA Figure S1. Schematic diagram of the interaction of PDA and Dox Figure S2. Schematic diagram of the interaction of PDA and Rhod Table S2. Cartesian coordinates (in Å) of optimized geometries at PM6 level Figure S3. Scanning electron microscope (SEM) images, size distribution, hydration diameter distribution and Zeta potential separately for PDA-Rhod Figure S4. Zeta potential distribution and hydration diameter distribution of PDA NPs and PDA- Rhod-Dox respectively. FT-IR spectra of PDA, PDA-Dox, PDA-Rhod,PDA-Rhod-Dox Figure S5. Dispersity and stability of PDA-Rhod-Dox in aqueous solution (a) and FBS solution (b) after 14 days Figure S6. MS spectra of dopamine, Rhod123 and dopamine-rhod123 corresponding to the retention time 4.600min on the chromatogram Figure S7. MS spectra of dopamine, Dox and dopamine-dox corresponding to the retention time 4.833min on the chromatogram Figure S8. Fluorescence image of HeLa cells stained with Dox and Mito-Tracker green Figure S9. Cytotoxicity of PDA nanoparticles with or without NIR incubated with HeLa cells...15 S1
2 Table S1. Binding energies of Dox, Rhod123 and PDA. Unit: kcal/mol. Binding energy Dox + Rhod123 (complex I) 0.5 PDA + Dox (complex II) 2.1 PDA + Rhod123 (complex III) 7.3 PDA + Dox + Rhod123 (complex IV) 6.7 Figure S1. Schematic diagram of the interaction of polydopamine and doxorubicin. Red dotted lines represent hydrogen bonds (the digital was the distance of O-H or N-H, unit: Å), orange solid lines represent π-π stacking. 2
3 Figure S2. Schematic diagram of the interaction of PDA and Rhod123. Red dotted lines represent hydrogen bonds (the digital was the distance of N-H, unit: Å), orange solid lines represent π-π stacking. Table S2. Cartesian coordinates (in Å) of optimized geometries at PM6 level. PDA + Dox Atomic Type Coordinates(Angstroms) X Y Z C C C C C C C C C C C C C C C C C C O
4 O C C C C C O C C O O O O O O N O C H H H H H H H H H H H H H H H H H H H H H H H H H H O C
5 H H H C C C C C C C H O H O H C C C C C C C C H H N O H O H C C C C C C C C H H N O H O H C
6 C C C C C C C H H N O H O H H N C H H PDA+Rhod123 Atomic Type Coordinates(Angstroms) X Y Z C C C C C C C C C C H C C C H H H H H C C C C
7 H C C H H H O N H H N H C O O C H H H C C C C C C C H O H O H C C C C C C C C H H N O H O H
8 C C C C C C C C H H N O H O H C C C C C C C C H H N O H O H H N C H H PDA + Dox + Rhod123 Atomic Coordinates(Angstroms) Type X Y Z C C C C C C C
9 C C C H C C C H H H H H C C C C H C C H H H O N H H N H C O O C H H H C C C C C C C C C C C
10 C C C C C C C O O C C C C C O C C O O O O O O N O C H H H H H H H H H H H H H H H H H H H H
11 H H H H H H O C H H H C C C C C C C H O H O H C C C C C C C C H H N O H O H C C C C C C C C
12 H H N O H O H C C C C C C C C H H N O H O H H N C H H
13 Figure S3. Scanning electron microscope (SEM) images, hydration diameter distribution, size distribution and Zeta potential separately for PDA-Rhod (a, b, c, d). Figure S4. Size distribution and hydration diameter distribution of PDA NPs (a, c ) and PDA- Rhod-Dox (b, d ) respectively. FT-IR spectra (e) of PDA(black), PDA-Dox(red), PDA- Rhod(blue), PDA-Rhod-Dox (green). 13
14 Figure S5. Dispersity and stability of PDA-Rhod-Dox in aqueous solution (a) and FBS solution (b) after 14 days. Figure S6. MS spectra of dopamine, Rhod123 and dopamine-rhod123 corresponding to the retention time 4.6 min on the chromatogram. Figure S7. MS spectra of dopamine, Dox and dopamine-dox corresponding to the retention time 4.8 min on the chromatogram. 14
15 Figure S8. (a) Fluorescence image of HeLa cells stained with Dox (λex: 488nm, λem: 570nm- 590nm). (b) Fluorescence image of HeLa cells stained with Mito-Tracker Green (λex: 488nm, λem: 510nm-530nm). (c) Merged image of Dox and Mito-Tracker green. The scale bar is 50μm. Figure S9. Cytotoxicity of PDA nanoparticles with or without NIR incubated with HeLa cells. 15
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Table S1 Selected bond lengths [Å] and angles [ ] for complexes 1 8. Complex 1. Complex 2. Complex 3. Complex 4. Complex 5.
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