Enhancing the anticancer properties of cardiac glycosides by neoglycorandomization

Langenhan et al. 10.1073/pnas.0503270102.

Supporting Information

Files in this Data Supplement:

Supporting Text
Supporting Table 1
Supporting Figure 5
Supporting Table 2
Supporting Figure 6
Supporting Table 3
Supporting Table 4
Supporting Table 5

Supporting Figure 5

Fig. 5. Hydrolytic stability of neoglycoside 4a.

Supporting Figure 6

Fig. 6. Reciprocal IC₅₀ values as a function of library member and cell line. Standard errors are depicted with error bars.

Table 1. Liquid chromatography/mass spectrometry information for neoglycoside library

Neo-glycoside	Calculatedmass, Da	Observedmass, Da	Purity, %	90% isomeric purity	Neo- glycoside	Calculated mass, Da	Observed mass, Da	Purity, %	90% isomeric purity
4b	566.7	566.7	97	+	4a	566.7	566.7	98	+
5b	536.6	536.6	98	–	5a	536.6	536.6	100	–
6b	536.6	536.6	99	–	6a	536.6	536.6	99	+
7b	550.7	550.7	97	+	7a	550.7	550.7	96	–
8b	550.7	550.7	100	+	8a	550.7	550.7	99	–
9b	550.7	550.7	21	–	9a	550.7	550.7	0	–
10b	550.7	550.7	100	–	10a	550.7	550.7	97	–
11b	548.7	548.7	100	+	11a	548.7	548.7	100	+
12b	568.6	568.6	88	–	12a	568.6	568.6	95	+
13b	568.6	568.6	100	+	13a	568.6	568.6	100	+
14b	536.6	536.6	97	+	14a	536.6	536.6	99	+
15b	536.6	536.6	95	+	15a	536.6	536.6	99	+
16b	568.5	568.5	91	–	16a	568.5	568.5	99	–
17b	566.7	566.7	100	–	17a	566.7	566.7	95	–
18b	566.7	566.7	98	+	18a	566.7	566.7	98	+
19b	566.7	566.7	65	–	19a	566.7	566.7	94	–
20b	566.7	566.7	88	–	20a	566.7	566.7	91	–
21b	566.7	566.7	96	–	21a	566.7	566.7	91	–
22b	566.7	566.7	93	–	22a	566.7	566.7	92	–
23b	536.6	536.6	99	+	23a	536.6	536.6	100	+
24b	536.6	536.6	99	+	24a	536.6	536.6	97	+
25b	566.7	566.7	89	+	25a	566.7	566.7	93	+
26b	566.7	566.7	90	–	26a	566.7	566.7	91	–
27b	566.7	566.7	88	–	27a	566.7	566.7	91	–
28b	566.7	566.7	52	–	28a	566.7	566.7	61	–
29b	566.7	566.7	61	–	29a	566.7	566.7	34	–
30b	548.7	548.7	98	+	30a	548.7	548.7	97	+
31b	578.7	578.7	62	–	31a	578.7	578.7	86	–
32b	536.6	536.6	96	+	32a	536.6	536.6	98	–
33b	354.6	354.6	98	+	33a	354.6	354.6	99	–
34b	607.7	607.7	97	–	34a	607.7	607.7	99	–
35b	728.8	728.8	92	+	35a	728.8	728.8	88	+
36b	728.8	728.8	64	+	36a	728.8	728.8	89	+
37b	728.8	728.8	96	+	37a	728.8	728.8	97	+
38b	580.7	580.7	70	–	38a	580.7	580.7	22	–
39b	566.7	566.7	89	+	39a	566.7	566.7	96	+
40b	566.7	566.7	96	+	40a	566.7	566.7	97	+
41b	562.7	562.7	87	–	41a	562.7	562.7	83	–
42b	566.7	566.7	89	+	42a	566.7	566.7	98	+

Table 2. Library member IC₅₀ values (μM) and standard errors

Cells		L- riboside (5b )	D- riboside (6b )	L- fucoside (7b )	D-fucoside (8b )	2-Deoxy-D- galactoside (9b )	3-deoxy-D- glucoside (10b )	6-Deoxy-D- glucoside (11b )	2-Deoxy-2-fluoro-D- glucoside (12b )	6-Deoxy-6-fluoro-D- glucoside (13b )
Du145	IC₅₀	0.30	0.72	0.7	3.9	7	0.8	6	9	5
Du145	SE	0.03	0.04	0.1	0.6	1	0.2	1	2	2
MCF7	IC₅₀	0.19	3.0	1.3	11	5.1	0.46	1.9	8	6.2
MCF7	SE	0.03	0.4	0.4	2	0.8	0.09	0.2	1	0.9
HCT-116	IC₅₀	0.018	1.3	1.2	7	10	1.8	2.3	8	4.8
HCT-116	SE	0.002	0.6	0.3	1	1	0.4	0.4	2	0.8
Hep 3B	IC₅₀	0.059	0.9	0.35	4.9	3.6	1.7	4.4	8	4.6
Hep 3B	SE	0.006	0.1	0.04	0.3	0.8	0.2	0.4	1	1.0
SF-268	IC₅₀	0.23	1.8	0.90	10	8