Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

Table 2 Competitive inhibition of Gal-3 binding to ASF by glycopolymers 24–39 determined by ELISA

Compound	M_n (g/mol)^a	Ð ^a	Sugar motif	n ^b	IC₅₀/glycan (μM)	IC₅₀ (μM)	r ^c_p	r_p/n^d
Lactose	342.3	n.a.	Galβ1, 4Glc	1	n.a.	137 ± 26	1	1
LacNAc	383.4	n.a.	Galβ1, 4GlcNAc	1	n.a.	53 ± 16	1	1
LacdiNAc ^e	424.4	n.a.	GalNAcβ1, 4GlcNAc	1	n.a.	64 ± 20	1	1
24	25,200	1.08	LacdiNAc-OEt-triazole	6.6 (4.4%)	62.9 ± 9.6	9.5 ± 1.5	7	1.0
25	27,300	1.10	LacdiNAc-OEt-triazole	11.9 (8.2%)	66.5 ± 14.9	5.6 ± 1.2	11	1.0
26	34,270	1.18	LacdiNAc-OEt-triazole	20.3 (12.5%)	66 ± 17	3.25 ± 0.85	20	1.0
27	34,000	1.20	LacdiNAc-OEt-triazole	23.9 (16.3%)	94 ± 19	3.92 ± 0.81	16	0.7
28	38,600	1.15	LacdiNAc-OEt-triazole	37.2 (29.0%)	126 ± 22	3.39 ± 0.60	19	0.5
29	21,700	1.10	LacdiNAc-N-triazole	3.7 (2.7%)	32.7 ± 7.9	8.6 ± 2.1	8	2.0
30	24,100	1.10	LacdiNAc-N-triazole	10.6 (8.1%)	27.5 ± 4.6	2.59 ± 0.44	25	2.3
31	30,800	1.12	LacdiNAc-N-triazole	18.2 (12.0%)	62 ± 20	3.4 ± 1.1	19	1.0
32	38,900	1.39	LacdiNAc-N-triazole	36.1 (24.8%)	128 ± 17	3.53 ± 0.46	18	0.5
33	31,500	1.07	LacdiNAc-OEt-DBCO	9.6 (5.7%)	54.2 ± 5.9	5.65 ± 0.69	11	1.2
34	28,600	1.06	LacdiNAc-N-DBCO	5.2 (3.0%)	84 ± 19	16.2 ± 3.7	4	0.8
35	28,300	1.18	LacdiNAc-N-triazole-Ph	5.6 (3.2%)	31.5 ± 0.85	5.62 ± 0.15	11	2.0
36	51,700	1.18	LacdiNAc-N-triazole-Ph	34.7 (15.7%)	139 ± 54	4.0 ± 1.5	16	0.5
37	43,400	1.24	LacdiNAc-OEt-triazole-Ph	29.9 (17.2%)	101 ± 20	3.37 ± 0.66	19	0.6
38	48,600	1.30	(LacdiNAc-OEt-triazole)₂Ph	28.0 (12.3%)	98 ± 20	3.5 ± 0.72	18	0.6
39	46,100	1.10	(LacdiNAc-N-triazole)₂Ph	29.8 (14.0%)	76.8 ± 16.9	2.58 ± 0.57	25	0.8

n.a. not applicable, Et, ethyl; Ph, phenyl
^aMolecular weight (M_n) and dispersity (Ð) of polymers were determined using GPC with MALS and RI detection. Glycopolymers 28 and 32 were analyzed using Superose 12 column and 0.3 M sodium acetate buffer, pH 6.5 as the mobile phase; otherwise TSKgel Super SW3000 column and methanol/0.3 M sodium acetate buffer, pH 6.5 (4/1, v/v) as the mobile phase was employed. For monovalent standards, we give M_w (g/mol)
^bAverage number of glycans per polymer chain (glycan content, mol. %); n = 1, monovalent standard
^cRelative potency, i.e. IC₅₀ (monovalent standard)/IC₅₀ (multivalent glycopolymer)
^dRelative potency per one glycan
^eSynthesis of LacdiNAc standard (Scheme 1) is described in the Experimental section

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