Caspase-1 Specific Light-up Probe with Aggregation-Induced Emission. Characteristics for Inhibitor Screening of Coumarin-Originated Natural.
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1 Supporting Information Caspase-1 Specific Light-up Probe with Aggregation-Induced Emission Characteristics for Inhibitor Screening of Coumarin-Originated Natural Products Hao Lin, ^ Haitao Yang, ^ Shuai Huang, ^Fujia Wang, ^ Dong-Mei Wang, ^ Bin Liu,*# Yi-Da Tang,* and Chong-Jing Zhang* ^ State Key Laboratory of Bioactive Substances and Functions of Natural Medicines and ^Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, China, # Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore, Fuwai Hospital, Chinese Academy of Medical Sciences, Beijing, China, * cheliub@nus.edu.sg tangyida@fuwaihospital.org zhangchongjing@imm.ac.cn S-1
2 1. Procedure for Measurement of UV vis and PL Spectra. 10 μl of 1 mm TPETH-2MAL stock solution in DMSO was added to 1990 μl of HEPES buffer to obtain a 5 μm solution. All the HEPES buffer used consists of 50 mm NaCl, 0.1% chaps, 10 mm EDTA, 5% Glycerol, and 10 mm DTT with ph = 7.2. The UV.vis absorption spectra were collected from 200 to 800 nm, while the PL spectra were recorded from 450 to 800 nm with excitation at 420 nm. The UV.vis and PL spectra of C1-P1, C1-P2 and C1-P3 were recorded under the same condition. For coumarin compounds and NH 2 -Coumarin, The UV.vis absorption spectra were collected from 200 to 800 nm, while the PL spectra were recorded from 350 to 650 nm with excitation at 340 nm. 2. Procedure for measurement of reactivity between three probes and caspase-1 in Aqueous Solution. To the well of 96-well plate was added HEPES buffer (96.5 μl), the probe (2 μl) and caspase-1 (1.5 ul, final concentration 100 pm). The plate was then placed in the microplate reader and monitored for 1 hour with the following setting: Ex = 420 nm, Em = 630 nm, Interval of the kinetic is 1 min. 3. Procedure for measurement of reactivity between C1-P3 and various enzymes in Aqueous Solution. To the well of 96-well plate was added HEPES buffer (96 μl), C1-P3 (2 μl) and various proteins (2 ul, final concentration 100 pm). The plate was then placed in the microplate reader and monitored for 1 hour with the following setting: Ex = 420 nm, Em = 630 nm, Interval of the kinetic is 1 min. 4. Procedure for inhibition evaluation between coumarin-originated natural products and caspase-1 in aqueous solution. To the well of 96-well plate was added HEPES buffer (94.5 μl), screened inhibitor (2 μl), and caspase-1 (1.5 μl). The mixture was incubated at room temperature for 30 mins, followed by addition of C1-P3 (2 μl). The plate was then placed in the microplate reader and monitored for 1 hour with the following setting: Ex = 420 nm, Em = 630 nm, Interval of the kinetic is 1 min. 5. Measurement of fluorescent quantum yield of C1-P1, C1-P2 and C1-P3 in absence or presence of caspase-1. We firstly prepared the solution of C1-P1 (6.25 M), C1-P2 (6.25 M), C1-P3 (6.25 M) and the reference compound (tris(bipyridine)ruthenium(ii) chloride, 4.0 M). The solutions of probes were then incubated with caspase-1 (100 pm) for 1 hour. UV vis and PL Spectra were then collected for all the solutions. The fluorescent quantum yield (Φ) was calculated with the following equation: S-2
3 where A is the absorbance at the excitation wavelength (440nm), I is the integrated fluorescence intensity calculated from the area under the emission spectrum from 500 to 800 nm, n is the refractive index of the solvents (for buffer solutions, no refractive index correction was made) and the subscripts R and ref stand for the samples and reference,respectively. An aqueous solution of [Ru(bpy)3] 2+ was used as a standard (0.04 in HEPES buffer). Figure S1 1 H NMR spectra of C1-P1 in DMSO-d 6 S-3
4 Figure S2 High resolution mass spectrum (Q-TOF) of C1-P1 Figure S3 1 H NMR spectra of C1-P2 in DMSO-d 6 S-4
5 Figure S4 High resolution mass spectrum (Q-TOF) of C1-P2 Figure S5 1 H NMR spectra of C1-P3 in DMSO-d 6 S-5
6 Figure S6 High resolution mass spectrum (Q-TOF) C1-P3 96-B6 #1762 RT: 5.04 AV: 1 NL: 3.74E7 T: FTMS + c ESI Full ms [ ] m/z Figure S7 Mass spectrum (ESI) of C1-P1 in the presence of caspase-1 S-6
7 96-B8 #2080 RT: 5.27 AV: 1 NL: 1.06E8 T: FTMS + c ESI Full ms [ ] m/z Figure S8 Mass spectrum (ESI) of C1-P2 in the presence of caspase-1 A28-G11 #1386 RT: 3.74 AV: 1 NL: 1.29E8 T: FTMS + c ESI Full ms [ ] m/z Figure S9 Mass spectrum (ESI) of C1-P3 in the presence of caspase-1 S-7
8 I/I0 Table S1 Fluorescent quantum yields of C1-P1, C1-P2 and C1-P3 in the absence and presence of caspase-1 (100 pm) Compound A (440 nm) I ( nm) Φ Ru-4uM-H 2 O C1-P M C1-P M-caspase C1-P2-10 M C1-P2-10 M-caspase C1-P M C1-P M-caspase M 10 M 5 M 2 M 1 M 0.5 M Time (min) Figure S10. Time dependent fluorescent change of various concentration of C1-P3 upon incubation with Caspase-1 (100 pm), Ex: 420 nm; Em: 630 nm. S-8
9 Emission (a.u.) A B Figure S11. HPLC profiles of incubation mixture between C1-P3 and caspase-3. (A) HPLC profile of probe C1-P3 only. (B) HPLC spectrum of Probe 3 (5 M) incubated with caspase-3 (100 pm) for 20 mins. Excitation wavelength of monitor is 365 nm C1-P3 C1-P3+caspase-1 C1-P3+caspase-8 C1-P3+caspase Figure S12. The fluorescence intensity of C1-P3 (10 M) upon incubation with caspase-1, caspase-7 and caspase-8 (100 pm), which was then measured by microplate reader. Ex = 420 nm. Em = 630 nm Time (min) S-9
10 PL intensity (a.u.) C1-P3 only Cas-1+YVAD-CMK+C1-P3 Cas-1+C1-P Time (min) Figure S13. C1-P3 could detect the inhibition to caspase-1 by commercial inhibitor (YVAD-CMK). The black line was the fluorescence intensity of probe (5 M) only. The blue line was fluorescence intensity of probe (5 M) incubated with caspase-1 (100 pm). The red line was fluorescence intensity of probe (5 M) incubated with caspase-1 (100 pm) which was pre-incubated with commercial inhibitor (YVAD-CMK, 20 M) for 30 min. Table S2. Structure of the 56 coumarin-originated natural products, Ac-YVAD-CMK and NH 2 -Coumarin compound 1 compound 2 compound 3 compound 4 compound 5 compound 6 compound 7 compound 8 compound 9 compound 10 compound 11 compound 12 compound 13 compound 14 compound 15 compound 16 S-10
11 compound 17 compound 18 compound 19 compound 20 compound 21 compound 22 compound 23 compound 24 compound 25 compound 26 compound 27 compound 28 compound 31 compound 29 compound 30 compound 32 compound 33 compound 34 compound 35 compound 36 compound 37 compound 38 compound 39 compound 40 compound 41 compound 42 compound 43 compound 44 compound 45 compound 46 compound 47 compound 48 S-11
12 compound 49 compound 50 compound 51 compound 52 compound 53 compound 54 compound 55 compound 56 compound 57 NH 2 -Coumarin A HPLC 图谱 : Ac-YVAD-AMC B NH 2 -Coumarin C Compound 22 + Caspase-1 + Ac-YVAD-AMC D Compound 22 + Ac-YVAD-AMC Figure S14 HPLC profile of A) commercial probe (Ac-YVAD-AMC); B) NH2-Coumarin; C) the mixture of Compound 22, caspase-1 and Ac-YVAD-AMC; D) the mixture of Compound 22 and Ac-YVAD-AMC. S-12
13 A Ac-YVAD-AMC B NH 2 -Coumarin C Compound 32 + Caspase-1 + Ac-YVAD-AMC D Compound 32 + Ac-YVAD-AMC Figure S15 HPLC profile of A) commercial probe (Ac-YVAD-AMC); B) NH2-Coumarin; C) the mixture of Compound 32, caspase-1 and Ac-YVAD-AMC; D) the mixture of Compound 32 and Ac-YVAD-AMC. A Ac-YVAD-AMC B NH 2 -Coumarin C Compound 42 + Caspase-1 + Ac-YVAD-AMC D Compound 42 + Ac-YVAD-AMC Figure S16 HPLC profile of A) commercial probe (Ac-YVAD-AMC); B) NH2-Coumarin; C) the mixture of Compound 42, caspase-1 and Ac-YVAD-AMC; D) the mixture of Compound 42 and Ac-YVAD-AMC. S-13
14 A Ac-YVAD-AMC B NH 2 -Coumarin C Compound 47 + Caspase-1 + Ac-YVAD-AMC D Compound 47 + Ac-YVAD-AMC Figure S17 HPLC profile of A) commercial probe (Ac-YVAD-AMC); B) NH2-Coumarin; C) the mixture of Compound 47, caspase-1 and Ac-YVAD-AMC; D) the mixture of Compound 47 and Ac-YVAD-AMC. A Ac-YVAD-AMC B NH 2 -Coumarin C Ac-YVAD-cmk + Caspase-1 + AC-YVAD-AMC D Ac-YVAD-cmk + AC-YVAD-AMC Figure S18 HPLC profile of A) commercial probe (Ac-YVAD-AMC); B) NH2-Coumarin; C) the mixture of AC-YVAD-cmk, caspase-1 and Ac-YVAD-AMC; D) the mixture of AC-YVAD-cmk and Ac-YVAD-AMC. S-14
Department of Chemical and Biomolecular Engineering, 4 Engineering Drive 4, National University of Singapore, Singapore,
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