Supporting Information. Chemoenzymatic Synthesis of Galectin Binding. Glycopolymers
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1 Supporting Information Chemoenzymatic Synthesis of Galectin Binding Glycopolymers Jessica H. Ennist, Henry R. Termuehlen, Samuel P. Bernhard, Mackenzie S. Fricke, and Mary J. Cloninger* Department of Chemistry and Biochemistry, 103 Chemistry and Biochemistry Building, Montana State University, Bozeman, MT 59717, United States. *Corresponding author: phone, ; , General method to determine GlcNAc/LacNAc functionalization of PAMAM dendrimers 6ad. MALDI-TOF MS spectra were obtained for acetylated glucosamine dendrimers 4a-d, and the change in the weighted average molecular weight, M w, was divided by the M w of the protected N-acetylglucosaminopyranoside derivative 3 denoted here as A (Equation (1)) to calculate the total number of monosaccharides that were appended to the PAMAM. This value was also determined by dividing the change in M w for deacetylated dendrimers 5a-d by the M w of the deprotected N-acetylglucosaminopyranoside denoted here as B (Equation (2)), and also by dividing the change in M w for acetylated N-acetylglucosamine dendrimers upon deprotection by 126 (the loss of 3 acetyl groups) denoted here as C (Equation (3)). The values obtained from these three methods for determining the total amount of N- acetylglucosaminopyranoside addition were averaged, denoted by D (Equation (4)). The change in M w upon galactose addition to the deacetylated N-acetylglucosamine dendrimers was divided S-1
2 by 162 (the addition of galactose) denoted here as E (Equation (5)) to calculate the total number of galactose units added to the GlcNAc dendrimers. Values of M W were rounded to two significant figures. For G6, a small amount of peak shouldering is observed from compound fragmentation that occurs during the laser desorption process. 1 H Nuclear Magnetic Spectroscopy (NMR) was used as a second method to determine the degree of functionalization with N- acetyllactosamine. Through integration analysis of heterogeneously PAMAMbased dendrimers 6a-d, the degree of LacNAc functionalization was determined by the integration of the H-1 N-acetylglucosamine resonance (4.35 ppm), which was set to one proton, and the resonance of H-galactose resonance (4.44 ppm). The integration of the resonance at 4.44 ppm was multiplied by D which is denoted by F (Equation (6)) to give the total addition of galactose. These two methods to determine the total number of galactose added to the dendrimer were then averaged, denoted as G (Equation (7)). Sample numbers using data from compound 6c (G(4) PAMAM based) are provided in the equations below. Spectra were obtained on a Bruker DRX 600 MHz Spectrometer at room temperature. Integration rates were compared at a variety of T1 relaxation rates, and T1 rates were optimized for each dendrimer generation. 1 H NMR was also used as a secondary method of characterizing the degree of dendrimer functionalization with GlcNAc by comparing integration values for peaks from the GlcNAc endgroup with integration values for peaks from the resonances of protons from the interior of the PAMAM dendrimer framework. The calculated M w and functionalization of dendrimers 6a-d are shown in Table S1. A = Mw (Protected GlcNAc) - Mw (PAMAM) = = 45 (eq 1) B = Mw (Deprotected GlcNAc) - Mw (PAMAM) = = 47 (eq 2) S-2
3 C = Mw (Protected GlcNAc) - Mw (Deprotected GlcNAc) = = 40 (eq 3) D = A + B + C = = 44 (eq 4) 3 3 E = Mw (LacNAc) - Mw (Deprotected GlcNAc) = = 43 (eq 5) F = ʃ (4.45ppm) x D = 0.89 x 44 = 39 (eq 6) G = E + F = = 41 (eq 7) 2 2 Table S1. Functionalization and MW values for LacNAc dendrimers. Compound GlcNAc Functionalization LacNAc Functionalization (G) MW (g/mol) 6a b c d S-3
4 Spectral Data Figure 1: 1 H NMR spectrum (500 MHz, d6-dmso) of 3. S-4
5 Figure 2: 13 C NMR spectrum (126 MHz, CDCl3) of 3. S-5
6 Figure 3: 1 H- 1 H COSY spectrum (500 MHz, d6-dmso) of 3. S-6
7 Figure 4: 1 H NMR spectrum (500 MHz, d6-dmso) of 4a. S-7
8 Figure 5: 13 C NMR spectrum (126 MHz, d6-dmso) of 4a. S-8
9 Figure 6: 1 H NMR spectrum (500 MHz, d6-dmso) of 4b. S-9
10 Figure 7: 13 C NMR spectrum (126 MHz, d6-dmso) of 4b. S-10
11 Figure 8: 1 H NMR spectrum (500 MHz, d6-dmso) of 4c. S-11
12 Figure 9: 13 C NMR spectrum (126 MHz, d6-dmso) of 4c. S-12
13 Figure 10: 1 H NMR spectrum (500 MHz, d6-dmso) of 4d. S-13
14 Figure 11: 13 C NMR spectrum (126 MHz, d6-dmso) of 4d. S-14
15 Intens m/z 0_G5\1: +MS, Smoothed (2.00,100,GA) Figure 12: Smoothed MALDI TOF spectrum for compound 4a. Mw = 8,300 g/mol. Intens m/z 0_D9\1: +MS, Smoothed (3.40,10,GA), Smoothed (3.40,10,GA), Smoothed (3.40,100,GA) Figure 13: Smoothed MALDI TOF spectrum for compound 4b. Mw = 17,800 g/mol. S-15
16 Intens m/z 0_M3\1: +MS, Smoothed (4.68,100,GA) Figure 14: Smoothed MALDI TOF spectrum for compound 4c. Mw = 35,000 g/mol. Intens m/z 0_C1\1: +MS, Smoothed (18.15,100,GA) Figure 15: Smoothed MALDI TOF spectrum for compound 4d. Mw = 119,600 g/mol. S-16
17 Figure 16: 1 H NMR spectrum (500 MHz, d6-dmso) of 5a. S-17
18 Figure 17: 13 C NMR spectrum (126 MHz, d6-dmso) of 5a. S-18
19 Figure 18: 1 H NMR spectrum (500 MHz, d6-dmso) of 5b. S-19
20 Figure 19: 13 C NMR spectrum (126 MHz, d6-dmso) of 5b. S-20
21 Figure 20: 1H NMR spectrum (500 MHz, d6-dmso) of 5c. S-21
22 Figure 21: 13 C NMR spectrum (126 MHz, d6-dmso) of 5c. S-22
23 Figure 22: 1 H NMR spectrum (500 MHz, d6-dmso) of 5d. S-23
24 Figure 23: 13 C NMR spectrum (126 MHz, d6-dmso) of 5d. S-24
25 Intens m/z 0_G1\1: +MS, Smoothed (1.54,100,GA) Figure 24: Smoothed MALDI TOF spectrum for compound 5a. Mw = 7,000 g/mol. ntens m/z 0_F3\1: +MS, Smoothed (0.00,100,GA) Figure 25: Smoothed MALDI TOF spectrum for compound 5b. Mw = 14,100 g/mol. S-25
26 Intens m/z 0_P7\1: +MS, Smoothed (4.67,100,GA) Figure 26: Smoothed MALDI TOF spectrum for compound 5c. Mw = 35,000 g/mol. Intens m/z 0_H2\1: +MS, Smoothed (0.00,10,GA) Figure 27: Smoothed MALDI TOF spectrum for compound 5d. Mw = 104,600 g/mol. S-26
27 Figure 28: 1 H NMR spectrum (600 MHz, d6-dmso) of 6a. S-27
28 Figure 29: 13 C NMR spectrum (151 MHz, d6-dmso) of 6a. S-28
29 Figure 30: 1 H NMR spectrum (600 MHz, d6-dmso) of 6b. S-29
30 Figure 31: 13 C NMR spectrum (151 MHz, d6-dmso) of 6b. S-30
31 Figure 32: 1 H NMR spectrum (600 MHz, d6-dmso) of 6c. S-31
32 Figure 33: 13 C NMR spectrum (151 MHz, d6-dmso) of 6c. S-32
33 Figure 34a: 1 H NMR spectrum (600 MHz, d6-dmso) of 6d. S-33
34 Figure 34b: 1 H- 1 H COSY spectrum (500 MHz, d6-dmso) of 6d. S-34
35 Figure 35: 13 C NMR spectrum (151 MHz, d6-dmso) of 6d. S-35
36 Intens m/z 0_G5\1: +MS, Smoothed (2.00,100,GA) Figure 36: Smoothed MALDI TOF spectrum for compound 6a. Mw = 8,700 g/mol. Intens m/z 0_J8\1: +MS, Smoothed (0.00,100,GA), Smoothed (0.00,100,GA), Smoothed (0.86,100,GA) Figure 37: Smoothed MALDI TOF spectrum for compound 6b. Mw = 16,400 g/mol. S-36
37 Intens m/z 0_I16\1: +MS, Smoothed (4.21,100,GA) Figure 38: Smoothed MALDI TOF spectrum for compound 6c. Mw = 37,000 g/mol. Intens m/z 0_N2\1: +MS, Smoothed (0.00,1,GA) Figure 39: Smoothed MALDI TOF spectrum for compound 6d. Mw = 119,400 g/mol. S-37
38 Cellular Assay Data The following SI Figures are primary data from cellular aggregation assays. Images shown are composed of 12 compressed stills taken at 10x magnification then manipulated to black and white (SI Figures 40 to Error! Reference source n ot found.). SI Figure 44: A µm G2-Nacetyllactosamine SI Figure 45: A-549, galectin-3, 0 µm G2-N-acetyllactosamine SI Figure 49: A-549, galectin-3, and 135 µm G2-N-acetyllactosamine SI Figure 50:A µm G3-Nacetyllactosamine SI Figure 40: A µm G2-Nacetyllactosamine SI Figure 46: A-549, galectin-3, and 34 µm G2-N-acetyllactosamine SI Figure 51: A µm G3-Nacetyllactosamine SI Figure 41: A µm G2-Nacetyllactosamine SI Figure 47: A-549, galectin-3, and 68 µm G2-N-acetyllactosamine SI Figure 52: A µm G3-Nacetyllactosamine SI Figure 42: A µm G2-Nacetyllactosamine SI Figure 48: A-549, galectin-3, and 101 µm G2-N-acetyllactosamine SI Figure 53: A µm G3-Nacetyllactosamine SI Figure 43: A µm G2-Nacetyllactosamine S-38
39 SI Figure 54: A µm G3-Nacetyllactosamine SI Figure 59: A-549, galectin-3, and 72 µm G3-N-acetyllactosamine SI Figure 64: A µm G4-Nacetyllactosamine SI Figure 55: A-549, galectin-3, 0 µm G3-N-acetyllactosamine SI Figure 60: A µm G4-Nacetyllactosamine SI Figure 65: A-549, galectin-3, 0 µm G4-N-acetyllactosamine SI Figure 56: A-549, galectin-3, and 18 µm G3-N-acetyllactosamine SI Figure 61: A µm G4-Nacetyllactosamine SI Figure 66: A-549, galectin-3, 8 µm G4-N-acetyllactosamine SI Figure 57: A-549, galectin-3, and 36 µm G3-N-acetyllactosamine SI Figure 62: A µm G4-Nacetyllactosamine SI Figure 67: A-549, galectin-3, 16 µm G4-N-acetyllactosamine SI Figure 58: A-549, galectin-3, and 54 µm G3-N-acetyllactosamine SI Figure 63: A µm G4-Nacetyllactosamine SI Figure 68: A-549, galectin-3, 24 µm G4-N-acetyllactosamine S-39
40 SI Figure 69: A-549, galectin-3, 32 µm G4-N-acetyllactosamine SI Figure 74: A µm G6-Nacetyllactosamine SI Figure 79: A-549, galectin-3, 12 µm G6-N-acetyllactosamine SI Figure 70: A µm G6-Nacetyllactosamine SI Figure 75: A-549, galectin-3, 0 µm G6-N-acetyllactosamine SI Figure 80: HT µm G2-Nacetyllactosamine SI Figure 71: A µm G6-Nacetyllactosamine SI Figure 76: A-549, galectin-3, 3 µm G6-N-acetyllactosamine SI Figure 81: HT µm G2-Nacetyllactosamine SI Figure 72: A µm G6-Nacetyllactosamine SI Figure 77: A-549, galectin-3, 6 µm G6-N-acetyllactosamine SI Figure 82: HT µm G2-Nacetyllactosamine SI Figure 73: A µm G6-Nacetyllactosamine SI Figure 78: A-549, galectin-3, 9 µm G6-N-acetyllactosamine SI Figure 83: HT µm G2-Nacetyllactosamine S-40
41 SI Figure 84: HT µm G2-Nacetyllactosamine SI Figure 89: HT-1080, galectin-3, 20 µm G2-N-acetyllactosamine SI Figure 94: HT µm G3-Nacetyllactosamine SI Figure 85: HT µm G2-Nacetyllactosamine SI Figure 90: HT-1080, galectin-3, 34 µm G2-N-acetyllactosamine SI Figure 95: HT µm G3-Nacetyllactosamine SI Figure 86: HT µm G2-Nacetyllactosamine SI Figure 91: HT-1080, galectin-3, 68 µm G2-N-acetyllactosamine SI Figure 96: HT µm G3-Nacetyllactosamine SI Figure 87: HT-1080, galectin-3, 0 µm G2-N-acetyllactosamine SI Figure 92: HT-1080, galectin-3, 101 µm G2-N-acetyllactosamine SI Figure 97: HT µm G3-Nacetyllactosamine SI Figure 88: HT-1080, galectin-3, 10 µm G2-N-acetyllactosamine SI Figure 93: HT-1080, galectin-3, 135 µm G2-N-acetyllactosamine SI Figure 98: HT µm G3-Nacetyllactosamine S-41
42 SI Figure 99: HT µm G3-Nacetyllactosamine SI Figure 104: HT-1080, galectin-3, 54 µm G3-N-acetyllactosamine SI Figure 109: HT µm G4-Nacetyllactosamine SI Figure 100: HT µm G3-Nacetyllactosamine SI Figure 105: HT-1080, galectin-3, 72 µm G3-N-acetyllactosamine SI Figure 110: HT µm G4-Nacetyllactosamine SI Figure 101: HT-1080, galectin-3, 0 µm G3-N-acetyllactosamine SI Figure 106: HT µm G4-Nacetyllactosamine SI Figure 111: HT-1080, galectin-3, 0 µm G4-N-acetyllactosamine SI Figure 102: HT-1080, galectin-3, 18 µm G3-N-acetyllactosamine SI Figure 107: HT µm G4-Nacetyllactosamine SI Figure 112: HT-1080, galectin-3, 8 µm G4-N-acetyllactosamine SI Figure 103: HT-1080, galectin-3, 36 µm G3-N-acetyllactosamine SI Figure 108: HT µm G4-Nacetyllactosamine SI Figure 113: HT-1080, galectin-3, 16 µm G4-N-acetyllactosamine S-42
43 SI Figure 114: HT-1080, galectin-3, 24 µm G4-N-acetyllactosamine SI Figure 119: HT µm G6-Nacetyllactosamine SI Figure 124: HT-1080, galectin-3, 9 µm G6-N-acetyllactosamine SI Figure 115: HT-1080, galectin-3, 32 µm G4-N-acetyllactosamine SI Figure 120: HT µm G6-Nacetyllactosamine SI Figure 125: HT-1080, galectin-3, 12 µm G6-N-acetyllactosamine SI Figure 116: HT µm G6-Nacetyllactosamine SI Figure 121: HT-1080, galectin-3, 0 µm G6-N-acetyllactosamine SI Figure 126: DU µm G2-Nacetyllactosamine SI Figure 117: HT µm G6-Nacetyllactosamine SI Figure 122: HT-1080, galectin-3, 3 µm G6-N-acetyllactosamine SI Figure 127: DU µm G2-Nacetyllactosamine SI Figure 118: HT µm G6-Nacetyllactosamine SI Figure 123: HT-1080, galectin-3, 6µM G6-N-acetyllactosamine SI Figure 128: DU µm G2-Nacetyllactosamine S-43
44 SI Figure 129: DU µm G2-Nacetyllactosamine SI Figure 134: DU-145, galectin-3, 10 µm G2-N-acetyllactosamine SI Figure 139: DU-145, galectin-3, 135 µm G2-N-acetyllactosamine SI Figure 130: DU µm G2-Nacetyllactosamine SI Figure 135: DU-145, galectin-3, 20 µm G2-N-acetyllactosamine SI Figure 140: DU µm G3-Nacetyllactosamine SI Figure 131: DU µm G2-Nacetyllactosamine SI Figure 136: DU-145, galectin-3, 34 µm G2-N-acetyllactosamine SI Figure 141: DU µm G3-Nacetyllactosamine SI Figure 132: DU µm G2-Nacetyllactosamine SI Figure 137: DU-145, galectin-3, 68 µm G2-N-acetyllactosamine SI Figure 142: DU µm G3-Nacetyllactosamine SI Figure 133: DU-145, galectin-3, 0 µm G2-N-acetyllactosamine SI Figure 138: DU-145, galectin-3, 101 µm G2-N-acetyllactosamine SI Figure 143: DU µm G3-Nacetyllactosamine S-44
45 SI Figure 144: DU µm G3-Nacetyllactosamine SI Figure 149: DU-145, galectin-3, 72 µm G3-N-acetyllactosamine SI Figure 154: HT µm G2-Nacetyllactosamine SI Figure 145: DU-145, galectin-3, 0 µm G3-N-acetyllactosamine SI Figure 150: DU µm G4-Nacetyllactosamine SI Figure 155: DU-145, galectin-3, 0 µm G4-N-acetyllactosamine SI Figure 146: DU-145, galectin-3, 18 µm G3-N-acetyllactosamine SI Figure 151: DU µm G4-Nacetyllactosamine SI Figure 156: DU-145, galectin-3, 8 µm G4-N-acetyllactosamine SI Figure 147: DU-145, galectin-3, 36 µm G3-N-acetyllactosamine SI Figure 152: DU µm G4-Nacetyllactosamine SI Figure 157: DU-145, galectin-3, 16 µm G4-N-acetyllactosamine SI Figure 148: DU-145, galectin-3, 54 µm G3-N-acetyllactosamine SI Figure 153: DU µm G4-Nacetyllactosamine SI Figure 158: DU-145, galectin-3, 24 µm G4-N-acetyllactosamine S-45
46 SI Figure 159: DU-145, galectin-3, 32 µm G4-N-acetyllactosamine SI Figure 164: DU µm G6-Nacetyllactosamine SI Figure 169: DU-145, galectin-3, 0 µm G6-N-acetyllactosamine SI Figure 160: DU µm G6-Nacetyllactosamine SI Figure 165: DU-145, galectin-3, 0 µm G6-N-acetyllactosamine SI Figure 161: DU µm G6-Nacetyllactosamine SI Figure 166: DU-145, galectin-3, 3 µm G6-N-acetyllactosamine SI Figure 162: DU µm G6-Nacetyllactosamine SI Figure 167: DU-145, galectin-3, 6 µm G6-N-acetyllactosamine SI Figure 163: DU µm G6-Nacetyllactosamine dendrimer SI Figure 168: DU-145, galectin-3, 9 µm G6-N-acetyllactosamine S-46
47 1 0 0 % F re e C e lls U n tr e a te d C e lls L a c N A c C o n c e n tr a tio n, m M Figure S170. Results of LacNAc monomer on galectin-3 induced homotypic aggregation of A549 cells. % Free Cells With Galectin A 549 G2-GlcNAc Control 0 Untreated Cells Dendrimer Concentration, µm Figure S172. Results of GlcNAc dendrimer 5a on galectin-3 induced homotypic aggregation of A549 cells. In Scheme 1, n = 6 for this compound 5a. S-47
48 % Free Cells Without Galectin-3 With Galectin Untreated Cells A549 G4-GlcNAc Dendrimer Concentration, µm Figure S173. Results of GlcNAc dendrimer 5c on galectin-3 induced homotypic aggregation of A549 cells. In Scheme 1, n = 42 for this compound 5c. % Free Cells Without Galectin Untreated Cells A 549 G6-GlcNAc Control Dendrimer Concentration, µm Figure S174. Results of GlcNAc dendrimer 5d on galectin-3 induced homotypic aggregation of A549 cells. In Scheme 1, n = 144 for this compound 5d. S-48
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