Table 1.

Inhibition of tubulin polymerization, percent inhibition of colchicine binding, and cytotoxicity of the benzosuberene and dihydronaphthalene analogues.

Compound	Inhibition of tubulin polymerization IC50 (μM) ± SD	% Inhibition of colchicine binding ± SD	GI50 (μM) SRB assaya
			SK-OV-3	NCI-H460	DU-145
CA4	1.0b	84 ± 3 (1 μM), 98 ± 0.007 (5 μM)	0.00455	0.00223c	0.00327c
CA4P	>40b	ND	0.00119	0.00194c	0.00323c
KGP18	0.85 ± 0.02d	73 ± 5 (1 μM), 95 ± 0.5 (5 μM)	0.0000543e	0.0000418e	0.0000249e
KGP03	0.5f	90 ± 2 (1 μM), 98 ± 0.3 (5 μM)	0.0029f	0.0032f	0.00040f
Doxorubicin	ND	ND	0.0789	0.123	0.134
Paclitaxel	NR	NR	0.00134	0.00176	0.00147
3	>20	ND	0.394	0.173	0.0330
6	1.2 ± 0.1	72 ± 2 (5 μM)	0.0314	0.0476	0.141
8	>20	ND	6.52	1.90	5.66
11	>20	ND	3.22	0.855	3.76
13	0.39 ± 0.06	88 ± 1 (5 μM)	0.0221	0.0353	0.0362
14	4.9 ± 0.1	35 ± 5 (1 μM)	0.312	0.449	0.423
15	>20	0 (5 μM)	3.03	3.86	4.04
18	1.1 ± 0.1	62 ± 0.7 (5 μM)	0.0648	0.434	0.860
19	0.37 ± 0.08	73 ± 0.6 (5 μM)	0.0384	0.0605	0.0252
20	3.2 ± 0.08	61 ± 3 (5 μM)	0.0572	0.0847	0.0402
27	1.0 ± 0.07	47 ± 1 (5 μM)	0.299	0.353	0.631
28	0.63 ± 0.03	76 ± 2 (5 μM)	0.0403	0.0628	ND
37	3.8 ± 0.5	28 ± 4 (5 μM)	0.263	0.432	0.439
49	>20	0.4 ± 0.6 (5 μM)	ND	0.334	1.20g
56	>20	0 (5 μM)	27.2	70.5	26.0
57	>20	0 (5 μM)	5.77	2.00	4.45
68	0.48 ± 0.08	68 ± 1 (0.5 μM), 95 ± 0.8 (5 μM)	0.00690	0.0581	0.0976
69	16 ± 0.7	45 ± 2 (5 μM)	0.0153	0.0291	0.0239

^aAverage of n ≥ 3 independent determinations (unless otherwise noted)

^bData from ref. 24²⁴ and ref. 74⁷⁴

^cFor additional data, see ref. 24²⁴

^dFor additional data, see ref. 37³⁷

^eFor additional data, see ref. 8⁸

^fFor additional data, see ref. 36³⁶ and ref. 75⁷⁵

^gAverage of n = 2 independent determinations (of duplicates)

ND = Not Determined

NR = Not Relevant (paclitaxel enhances microtubule assembly)