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1 Supporting Information for Near-Infrared Fluorescent Turn-On Probe with a Remarkable Large Stokes Shift for Imaging Selenocysteine in Living Cells and Animals Weiyong Feng, Meixing Li, Yao Sun, and Guoqiang Feng* Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 4379, P. R. China gf256@mail.ccnu.edu.cn Table of contents: 1. Table S1 Page S2-S3 2. Structure characterizations of compound 2 and probe 1 Page S3-S6 3. Additional data and spectra Page S6-S12 S-1

2 1. Table S1. A comparison of the fluorescent probes for Sec detection. Probe for Sec Selective λ abs /λ em Stokes NIR Detection Linear (Ref.) detection shift emission limit range of Sec at physiological ph (7.4) No ~49/52 ~3 No 4 nm.5-5μm (.8 (1-1 pmol/well, pmol/well, (Angew. Chem., Int. based on a based on a Ed. 26, 45, microtiter microtiter ) plate plate assay) assay) Yes 69/ Yes Not -4 μm reported (Chem.-Eur. J. 215, 21, ) (Chem.Commun. 215, 51, ) Yes 4/58 Yes 38/ No 7. nm -2 μm 55 No 18 nm 1-2 μm (Anal. Chem. 216, 88, ) Yes 37/52 32 No 62 nm -1 μm (J. Am. Chem. Soc. 215, 137, ) Yes 3/55 19 NO ~15 nm -.5 μm (Anal. Chem. S-2

3 216, 88, ) Yes 45/52 7 No 23 nm.2-3 μm (Anal. Chem. 217, 87, ) NC CN O O 2N O N H S O (This work) NO 2 Yes 478/ Yes nm -7 μm 2. Structure characterizations of compound 2 and probe DMSO H 2 O 1 H-NMR spectrum of compound 2 in DMSO-d6 S-3

4 C-NMR spectrum of compound 2 in DMSO-d6 MS (ESI) spectrum of compound 2 S-4

5 1 H-NMR spectrum of probe 1 in DMSO-d6 13 C-NMR spectrum of probe 1 in DMSO-d6 S-5

6 HR-MS spectrum of probe 1 3. Additional data and spectra (a) 9 3 probe 1 + Sec probe 1 probe 1 + DTT probe 1 + (Sec) 2 (b) probe 1 + Sec 1 + DTT probe Sec 1 + DTT 1 + (Sec) Time (min) Wavelength () Figure S1. (a) Fluorescence kinetics of probe 1 (1 µm) upon addition of Sec (1 µm), (Sec)2 (5 µm), and DTT (5 µm) in DMSO PBS buffer (1 mm, ph 7.4, 1 : 1, v/v) at 37. All the reaction were monitored at 67 with λex = 49, dex = dex = 1. (b) Fluorescence spectra changes of probe 1 (1 µm) upon addition of Sec (1 µm), (Sec)2 (5 µm), and DTT (5 µm). Note: A mixture of 5 µm of (Sec)2 and 5 µm of DTT can produce 1 µm of Sec (Ref.: Maeda, H.; Katayama, K.; Matsuno, H.; Uno, T. Angew. Chem., Int. Ed. 26, 45, ). S-6

7 (a).5 (b) compound Abs min Abs.3.2 probe Wavelength () Wavelength () Figure S2. (a) UV-vis spectra changes of probe 1 (1 µm) upon addition of Sec (1 µm). (b) UV-vis spectra of probe 1 (1 μm) and compound 2 (1 μm). All spectra were measured in DMSO-PBS buffer (1 mm, ph 7.4, 1:1, v:v) at 37 C. (a) 1 (b) probe 1 + anions Wavelength () probe 1 + Sec (67 ) Analytes Figure S3. (a) Fluorescence responses of probe 1 (1 μm) upon addition of 1 μm of Sec and various anions. (b) Fluorescent detection of Sec with probe 1 in the presence of different anions: (1) F, (2) Cl, (3) Br, (4) I, (5) AcO, (6) HCO3, (7) N3, (8) NO3, (9) SO4 2, (1) SCN, (11) C2O4 2, (12) S2O7 2, (13) HSO3, (14) HS, (15) CN, (16) ClO, (17) NO2, (18) HPO4 2, and (19) SeO3 2. Black bars represent the addition of a single anion (1 μm). Red bars represent the subsequent addition of Sec (1 μm) to the mixture. All experiments were performed in DMSO-PBS buffer (1 mm, ph 7.4, 1 : 1, v/v) at 37 and each data was obtained 1 min after mixing. S-7

8 (a) 1 (b) probe 1 + metal ions probe 1 + Sec Wavelength () Figure S4. (a) Fluorescence responses of probe 1 (1 μm) upon addition of 1 μm of Sec and various metal ions. (b) Fluorescent detection of Sec with probe 1 in the presence of different metal ions: (1) Li +, (2) Na +, (3) K +, (4) Mg 2+, (5)Al 3+, (6) Zn 2+, (7) Mn 2+, (8) Co 2+, (9) Cd 2+, (1) Ni 2+, (11) Ca 2+, (12) Hg 2+, (14) Cu 2+, (15) Fe 2+, (16) Fe 3+, and (17) Ag +. Black bars represent the addition of a single metal ion (1 μm). Red bars represent the subsequent addition of Sec (1 μm) to the mixture. All experiments were performed in DMSO-PBS buffer (1 mm, ph 7.4, 1 : 1, v/v) at 37 and each data was obtained 1 min after mixing. 1 probe 1 + Sec ph probe 1 Figure S5. The fluorescence responses of probe 1 (1 μm) at 67 in the absence and presence of 1 equiv Sec at different phs. All experiments were performed in PBS buffer (1 mm) with 5% DMSO at 37 C and each data was obtained 1 min after mixing. λex = 49, slit width: dex = dem = 1. S-8

9 Figure S6. Thin layer chromatography (TLC) analysis of the reaction of probe 1 with 1 equiv of Sec in PBS buffer (1 mm, ph 7.4, with 5% DMSO, v/v) at 37 C. (A) Under room light. (B) Under light of 254. (C) Under light of 365. Spots on the silica TLC plate are: a. probe 1; b. the sample from the reaction of probe 1 and Sec after 2 min; c. mixture of b and reference compound 2; d. the reference sample of compound 2, respectively. The eluent for TLC: hexane/ethyl acetate = 3:1 (v/v). (a) reference of compound 2 t = 1.9 min (b) Analysis of the reaction mixure of probe 1 with Sec This peak increased. This peak decreased. reaction time at 2 min probe 1 t = min reaction time at 1 min 1 2 Retention time/min 1 2 Retention time/min Figure S7. The results of HPLC analyses. (a) The traces of reference samples of probe 1 and compound 2. (b) The traces of the reaction mixture of probe 1 with Sec at different reaction times (1 and 2 min). Column: RP-C18 column (4.6 mm 15 mm) from Agilent Technologies. Eluent: CH3OH/H2O = 65:35 (v/v, with.5%tfa). Flow rate: 1. ml/min. Temperature: 25 C. Detection wavelength: 49. S-9

10 2 + H + Figure S8. Mass spectrum of the reaction mixture of probe 1 and Sec. The peak found at can be assigned to 2 + H + (Calcd ), which proved the production of 2. 1 (67 ) sample contaning 1% FBS FBS free sample [Sec] M Figure S9. Fluorescent intensity changes of probe 1 (1 μm) at 67 for Sec (5, 1, 2, 3, 4, 5,, 7, 8, 9, 1, 15, 2, 25, 3, 4, and 5 μm) spiked samples in FBS (1%, v/v)-containing samples (data in blue ). For a comparison, the data in Figure 3a are included (data in red ). All the data were collected in DMSO-PBS buffer (1 mm, ph 7.4, 1:1, v/v) at 37 C and each data was obtained 1 min after mixing. S-1

11 1 8 Cell Viability Concentration of probe 1 ( M) Figure S1. Percentage of viable A549 cells after treatment with indicated concentrations of probe after 24 hours. The cell viability was observed via MTT assay. (a) 1 (b) min min Wavelength () Wavelength () Figure S11. (a) Fluorescence responses of probe 1 (1 μm) upon addition of 1 μm of Sec that was generated by incubation of 5 μm (Sec)2 with 1 μm Cys at 37 C for 3 min in PBS buffer (1 mm, ph 7.4). (b) Fluorescence responses of probe 1 (1 μm) upon addition of 1 μm of Sec that was generated by incubation of 5 μm (Sec)2 with 1 μm GSH at 37 C for 3 min in PBS buffer (1 mm, ph 7.4). All spectra were collected in DMSO-PBS buffer (1 mm, ph 7.4, 1:1, v/v) at 37 C. It should be noted that probe 1 is not responsive to Cys or GSH alone, see Figure 2. S-11

12 Figure S12. Probe 1 was used to study the metabolism of selenocompounds dibenzyl diselenide (DBDS) and SeO2 in living cells. (a) Cells were preincubated with DBDS (5 μm) for 1 h, 6 h and 12 h, and then treated with probe 1 (2 μm) for 3 min, respectively. (b) Cells were preincubated with SeO2 (5 μm) for 1 h, 6 h and 12 h, and then treated with probe 1 (2 μm) for 3 min, respectively. Top row of a and b: bright field images. Bottom row of a and b: the corresponding fluorescence images with excitation wavelength at Scale bar = 3 μm. S-12

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