Homogeneous Electrochemical Assay for Protein Kinase Activity

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1 Homogeneous Electrochemical Assay for Protein Kinase Activity Ik-Soo Shin,,, Rohit Chand, Sang Wook Lee, Hyun-Woo Rhee, Yong-Sang Kim, * and Jong-In Hong* Corresponding Author *Prof. Dr. J.-I. Hong, Department of Chemistry, Seoul ational University, Seoul (Korea), Fax: (+82) , jihong@snu.ac.kr *Prof. Dr.Y. S. Kim, School of Electronic and Electrical Engineering, Sungkyunkwan University, Suwon , Republic of Korea, yongsang@skku.edu Present Addresses Department of Chemistry, Soongsil University, Seoul , Republic of Korea School of atural Science, Ulsan ational Institute of Science and Technology (UIST), Ulsan , Republic of Korea S-1

2 Index Page 1. Preparation and characterization of probe S Cyclic voltammetry diagrams S The dependence of current response on the concentration of PKA S9 4. Modification of electrode S10 5. Fabrication of polymeric microchip S10 6. References S11 S-2

3 Preparation and characterization of probe S S O H 2 OH O O O O 2 MC, rt H OH 1 3 Scheme S1. Synthesis of compound 1 Synthesis of 3: Bis(DPA) analog 1 1 was chemically conjugated to 2 2. Active ester, 2, (0.7 g, 1.26 mmol) was dissolved in 10 ml of methylene chloride (MC) in a round bottom flask. 1 (0.7 g, 1.25 mmol) in 5 ml of MC was added over a period of 5 min with vigorous stirring. The reaction was left at room temperature overnight. Then, the reaction mixture was washed with water (2 20 ml). The organic layer was decanted carefully, dried over anhydrous a 2SO 4 and concentrated to yield brown sticky oil, which was chromatographed (neutral alumina gel, MC:MeOH = 100:1) to yield 3 (0.45 g, 35%). S-3

4 1 H-MR (CDCl 3, 300 MHz): δ (br m, 12H), (br, 2H), 1.54 (br,2h), 2.06 (t, 2H), 2.13 (t, 2H), 2.71 (t, 2H), 3.47 (d, 2H), 3.66 (s, 4H), 3.87 (s, 8H), 6.28 (s, 1H), 7.00 (s, 2H), 7.13 (t, 4H), 7.18 (t, 3H), 7.28 (t, 6H), 7.41 (d, 6H), 7.48 (d, 4H), 7.60 (t, 4H), 8.50 (d, 4H). S-4

5 13 C MR (CDCl 3, 75 MHz): δ , , , , , , , , , , , , , , 66.36, 59.84, 54.95, 40.43, 36.73, 34.60, 32.02, 29.70, (two carbon peaks, arrow marked ), 29.30, 29.15, 29.00, 28.59, HR FAB Mass: m/z calcd. for 3, chemical formula: C 64H 72 7O 2S [M + ]: , found S-5

6 S SH H O TESi, TFA H O OH MC, r t OH 3 Probe Scheme S2. Synthesis of probe Synthesis of Probe: 3 (0.1 g, 0.1 mmol) was dissolved in 10 ml of MC in a round bottom flask. With stirring, 1 ml of TFA and triethylsilane (TESi, 0.2 mmol) were added successively. The reaction mixture was stirred for 6 h. The reaction mixture was diluted with MC (20 ml) and washed with 0.1 M K 2CO 3 (2 30 ml) and brine (30 ml). The organic layer was decanted carefully, dried over anhydrous a 2SO 4 and concentrated to yield brown sticky oil, which was chromatographed (neutral alumina gel, MC:MeOH = 100:2) to yield Probe (0.03 g, 40 %). The synthesized probe was then immobilized on the electrode immediately. 1 H-MR (CDCl 3, 300 MHz): δ (br m, 12H), (br m, 4H), 2.06 (t,2h), 2.68 (m, 4H), 3.47 (br, 2H), 3.66 (s, 4H), 3.87 (s, 8H), 7.01 (s, 2H), 7.14 (t, 4H), 7.50 (d, 4H), 7.61 (t, 4H), 8.54 (d, 4H). S-6

7 Current (A) 2.0x x x10-5 Bare electrode (Au) 02 hrs of deposition 04 hrs of deposition 12 hrs of deposition 24 hrs of deposition -2.0x Potential Vs Ag/AgCl (V) Figure S1. Cyclic voltammetry of 5 mm potassium ferrocyanide in 0.1 M carbonate buffer (ph 9.2) at the bare gold electrode (solid line) and with different lengths of deposition time of the probe solution. Measurements were performed with a three-electrode system with Au (working electrode), 3 M acl Ag/AgCl (reference electrode) and platinum (counter electrode). Scan rate: 100 mv/s S-7

8 Figure S2. Cyclic voltammetry in 0.1 M carbonate buffer (ph 9.2) at the probe-immobilized electrode (blue), 100 µm phosphorylated ferrocene kemptide (black) and 100 µm non-phosphorylated ferrocene kemptide (red). Measurements were performed with a three-electrode system with gold (working electrode), 3 M acl Ag/AgCl (reference electrode) and platinum (counter electrode). Scan rate: 100 mv/s S-8

9 Figure S3. Plot for the dependence of current response on the concentration of protein kinase A in 0.1 M carbonate buffer (, see Figure 2b) and in blood serum (, see Table 1). S-9

10 Modification of electrode Commercial polycrystalline gold disc electrodes were cleaned according to the following protocol. They were immersed in chromic acid for three hours and rinsed thoroughly with deionized water. The electrodes were polished on polishing pads using alumina/water slurry. The polishing was followed by sonication in acetone, isopropyl alcohol and deionized water for 1 minute each. The electrodes were then electrochemically polished in 0.1 M sulfuric acid by cycling the potential between 0.5 V and 1.5 V until a stable voltammogram was seen. They were rinsed thoroughly with deionized water and alcohol, dried under nitrogen. The electrodes were finally dipped in probe solution for the required amount of time (Fig. S1). It is noted that the synthetic probe generally follows two steps of typical thiol adsorption kinetics; 1) a fast initial step of diffusion-controlled Langmuir adsorption, and 2) a second step where the alkyl chains in the probe molecules get out of the disordered state forming unit two-dimensional monolayer. As the length of a probe immobilization time increases, the amount of surface coverage, therefore, increases fast and then approaches a thermodynamic equilibrium between adsorption/desorption; which was reflected by the decrease in the current signal of CV. After formation of the monolayers, the modified electrodes were rinsed with the buffer and used for kinase assay. Fabrication of polymeric microchip A rapid prototyping technique for microfluidic systems based on a polymer film/double-sided tape was developed. For this purpose, we used transparent polyethersulfone (PES) films and 3M double sided tape. The chip was fabricated in three parts, where, the first bottom PES film layer contained the electrodes for electrochemical detection, the middle double-sided tape contained the fluidic network while the top PES film layer contained the inlet/outlet holes. A vacuum thermal evaporator was used to deposit electrodes. First, the PES film was cleaned by sonication in isopropyl alcohol followed by DI water and then dried under nitrogen gas. For laying the electrodes, a shadow mask containing the electrode pattern was attached to the cleaned substrate. Then, in a thermal vacuum evaporator, titanium layer was deposited on the glass wafer as an adhesion layer followed by a layer of gold for the working and the counter electrodes and silver for the reference electrode. The silver reference electrode was treated with 50 mm ferric chloride for 50 s and then rinsed with DI water to obtain a thin AgCl over the deposited Ag electrode. The fluidic network in tape was cut out using a commercial CO 2 laser cutter. Finally, the access holes were punched in the top PES film layer. The three layers were aligned under a simple optical microscope and kept under pressure for two hours. The above technique enabled a rapid prototyping of the microfluidic system without the use of a clean room facility and sophisticated instruments. S-10

11 References 1. Liu, G.; Choi, K. Y.; Bhirde, A.; Swierczewska, M.; Yin, J.; Lee, S. W.; Park, J. H.; Hong, J. I.; Xie, J.; iu, G.; Kiesewetter, D. O.; Lee, S.; Chen, X. Y., Angew. Chem. Int. Ed. 2012, 51, Liu, D. B.; Xie, Y. Y.; Shao, H. W.; Jiang, X. Y. Angew. Chem. Int. Ed. 2009, 48, S-11

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