Multifunctional multivalency: a focused library of polymeric cholera toxin antagonists
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1 Multifunctional multivalency: a focused library of polymeric cholera toxin antagonists Huu-Anh Tran, a,b Pavel I. Kitov, a Eugenia Paszkiewicz, a Joanna M. Sadowska, a and David R. Bundle a a Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada. Fax: (+1) ; Tel: (+1) ; dave.bundle@ualberta.ca b TheraCarb Inc st Street N.W. Calgary, Alberta CANADA T2L 2K7 ELISA Assay for Inhibition of Heat-labile Toxin (LT) To PVC microtiter plates (Gibco BRL Inc.) solution of coating compound 9 (1 μg/ml, 100 μl/well) in PBS buffer was added and incubated at room temperature overnight, then washed (6 ) with PBST (0.05 % Tween 20 in phosphate buffer saline, PBS). An inhibitor at decreasing concentrations (starting at 20 mg/ml, dilution factor 3.16; 50 μl/well) was mixed with LT (Sigma, 2 ng/ml) and the mixtures were applied to the plates. After incubation at room temperature for 2 h the plates were washed (6 ) with PBST. Rabbit anti-lt polyclonal antibody (Abcam Inc., dilution 1:10000, 100 μl/well) was added, incubated at room temperature for 1 h then the plates were washed (6 ) with PBST. Goat anti-rabbit IgG conjugated to horseradish peroxidase (Kirkegaard and Rerry Laboratories, dilution 1:5000, 100 μl/well) was added, incubated at room temperature for 30 min then the plates were washed (6 ) with PBST. 3,3:5,5-Tetramethylbenzidine solution (TMB purchased from KPL,100 μl/well) was added. After 15 min incubation the reaction was stopped by addition of H 3 P 4 (100 μl/well) and absorbance was measured at 450 nm. Table 1S. Inhibitory activities of heterobifunctional polymers against LT. Alkyne derivative 7.n α-gal polymer IC 50, μm a β-gal polymer IC 50, μm a F 5α27 (3%) β27 (3%) H N (h b =0.56) (h b =0.8) 5α27 (5%) β27 (5%) (h=0.54) (h=0.95) 5α27 (9%) (h=1.04) 5β27 (9%) (h=1.3) 6α27 (6.6%) (h=0.76) 6β27 (6.6%) (h=1.0) F 5α F H (5%) (h=1.3) N 5α (9%) (h=1.3) α28 (6.6%) (h=0.8) 6α28 (15%) (h=0.7) a activities per pendant ligand. b Hill coefficient 5β28 (5%) (h=1.1) 5β (9%) (h=1.4) 6β28 (6.6%) (h=0.74) 6β28 (15%) (h=0.7) S 1
2 Selected 1 H, 13 C NMR and IR spectra Ac Ac Ac Ac H N 3 3α f1 (ppm) S
3 Ac Ac Ac Ac H N 3 3β f1 (ppm) S 3
4 4α S 4
5 Ac Ac Ac Ac N 3 N 2 4β S 5
6 Dextran Aminated dextran S 6
7 H H H H N 3 H N 2 H N polyacrylamide 5α S 7
8 5β S 8
9 6α S 9
10 6β S 10
11 5α27 S 11
12 5β27 S 12
13 H H H F NH H N N N H N 2 H N dextran 6α27 S 13
14 6β27 S 14
15 f1 (ppm) S 15
16 Me S N H f1 (ppm) S 16
17 7.3 S 17
18 f1 (ppm) S 18
19 f1 (ppm) S 19
20 f1 (ppm) S
21 7.8 S 21
22 7.9 S 22
23 7.10 S 23
24 7.11 S 24
25 7.13 S 25
26 7.14 S 26
27 7.15 S 27
28 7.17 S 28
29 Me Me Me H N 7.18 S 29
30 7.19 S 30
31 f1 (ppm) S 31
32 f1 (ppm) S 32
33 f1 (ppm) S 33
34 f1 (ppm) S 34
35 f1 (ppm) S
36 F F H N f1 (ppm) S 36
37 f1 (ppm) S
38 F H N f1 (ppm) S 38
39 f1 (ppm) S
40 12 S 40
41 10 S 41
42 f1 (ppm) S 42
43 f1 (ppm) S 43
44 H H H H H H H AcHN - C H H H NHAc H H H H N H H S 44
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