TABLE 2

Antiproliferative activity of vitamin E analogs

Compounds are sorted by the signaling domain.


Compound Number

Functional Domain I (R1)

Signalling Domain II

Hydrophobic Domain III (R2)

IC50

Cell Type

References
μM
1 -O2CCH2CH2COO- 43 Jurkat, HBT11, MCF7, Birringer et al., 2003
2 CH3COO- a MCF7-C3
3 -O2CCH=CHCOO- 22
4 -O2CCH2CH(CH3)COO- b
5 -O2CCH2(CH2)2COO- b
6 -O2CCH2CH(CH3)CH2COO- b
7 -O2CCH2C(CH3)2CH2COO- b
8 -O2CC(CH3)2CH2CH2COO- b
9 H3COOCCH2CH2COO- b
10 -O2CCOO- c B16-F1/nude mice Kogure et al., 2005
11 -O2CCH2COO-
12 -O2CCH2CH2CONH- 13 Jurkat, U937, Meso-2 Tomic-Vatic et al., 2005
13 -O2CCH=CHCONH- 2
14 H3COOCCH2CH2CONH- >100
15 +NH3-CH2COO- a MCF7 Arya et al., 1998
16 +NH3Lys(NH3)COO- Embedded Image Embedded Image 12
17 Lys-Lys(Lys)COO- a
18 CH3O- a Jurkat Neuzil et al., 2001c
19 CH3CH2COO- d A549 Yano et al., 2005
20 -O2CCH2CH2CH2O- e LNCaP, PC-3 MDA-MB-453 Wu et al., 2004; Nishikawa et al., 2003
21 -O2CCH2O- f MDA-MB-435, MCF7 Shun et al., 2004
22 -O2CCH2- 15-20g MCF7 Shiau et al., 2006
23 (PEG)O2CCH2CH2COO- h Lung carcinoma cells/nude mice Youk et al., 2005
24 -O2C(CH2)5COO- a C127I Kogure et al., 2004
25 C2H5OOCCH2CH2COO- a
26 Nicotinic acid a
27 -O2CCH2CH(SePh)COO- Unknown Prostate Vraka et al., 2006
28 all-trans retinoic acid 0.1-1 NB4, HT93 Makishima et al., 1996, 1998
29 9-cis retinoic acid b
30 HOPO2O- b RASMC, THP-1 Munteanu et al., 2004
31 Toc-OPO2O- b
32 -O2CCH2CH2COO- Embedded Image 50% of α-TOS Jurkat, HBT11, MCF7, MCF7-C3, U937, Meso-2 Birringer et al., 2003; Tomic-Vatic et al., 2005
33 -O2CCH2CH2COO- Embedded Image b Jurkat, HBT11, MCF7, MCF7-C3 Birringer et al., 2003; Vraka et al., 2006
34 -O2CCH2CH(SePh)COO- b Prostate Vraka et al., 2006
35 -O2CCH2CH2COO- Embedded Image 66 Jurkat, HBT11, MCF7, MCF7-C3 Birringer et al., 2003; Tomic-Vatic et al., 2005
36 -O2CCH=CHCOO- 49 Jurkat, U937, Meso-2 Tomic-Vatic et al., 2005
37 -O2CCH2CH2CONH- 20
38 -O2CCH=CHCONH- 9
39 H3COOCCH2CH2COO- a Birringer et al., 2003
40
HO-


b
PC-3
Galli et al., 2004
  • a No effect.

  • b Inhibition of cell proliferation.

  • c Much more cytotoxic than α-TOS.

  • d Less effective than compound 54.

  • e The ether analog is less effective than α-TOS itself.

  • f Comparable with α-TOS.

  • g EC50 value in micrograms per milliliter.

  • h More efficient than α-TOS.