(14R)-14-hydroxy-4,14-retroretinol (14-HRR)

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1 Table S7 Atypical retinoids and retinoid-related molecules (RRMs) ame Chemical structure of the ligand(s) Mechanism of action and uses References Anhydroretinol (AR) Modulators of c-raf kinase 1-3 Blocks B lymphocyte proliferation as well as activation of resting T lymphocytes (14R)-14-hydroxy-4,14-retroretinol (14-RR) xidative stress and cell death 14 4 Growth-promoting properties in B-cells 4,5 4-ydroxyphenylretinamide (4-PR); Fenretinide Reduction of recurrent breast cancer in pre-menopausal women Patients who are undergoing surgical resection for recurrent glioblastoma multiforme (phase II) Recurrent hormone-naive prostate cancer (phase II) hormone-refractory prostate cancer varian epithelial or primary peritoneal cancer (phase II) ATURE REVIEWS DRUG DISCVERY ature Publishing Group

2 4-amino-2-(butyrylamino)phenylretinamide (ABP or CBG41) 2 resistant neuroblastoma (phase II) Patients with advanced solid tumors (phase I) Bladder cancer (phase III) CT116 colon cancer and other cell lines 6 Mofarotene (Ro ) Aminoarotinoid Regression of chemicallyinduced mammary tumors in rats More potent (70x) than ATRA in neoplastic cells derived from pancreatic and gastrointestinal tissues 7 8 Potent apoptotic actvity in 2 MDR cells 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2- naphthalenecarboxylic acid (AP/CD437) C Apoptotic activity in preclinical models of leukemia and carcinoma both in vitro and in vivo. Apoptogenic activity in retinoid-resistant cells and in 9-11 ATURE REVIEWS DRUG DISCVERY ature Publishing Group

3 RARγ-negative cells ST1926 (APC) 3-Cl-APC 3-A-APC Cl C Similar to AP Potent apoptotic activity associated with an early genotoxic stress C C Activates F-kB with apoptosis in a number of cancer cells Antagonizes cell-apoptotic events, but not antiproliferative events induced by AP MX781 (CD2674) Ac C Antiproliferative activity Induction of apoptosis via caspase 2 Inhibiton of IkB kinase 15 ATURE REVIEWS DRUG DISCVERY ature Publishing Group

4 AG193,918 C Inhibition of pancreatic cancer cell proliferation via supression of cell cycle regulatory protein function and induction of caspaseassociated apoptosis 16 Acyclic Retinoid (AR, IK333, polyprenoic acid) C 2 Chemoprevention of hepatocellular carcinoma 17 SetA2 S S 2 Apoptosis in squamous carcinoma cells (receptor independent/mitochondria dependent pathway) 18 References 1. Korichneva, I. & ammerling, U. F-actin as a functional target for retro-retinoids: a potential role in anhydroretinol-triggered cell death. J Cell Sci 112 ( Pt 15), (1999). 2. Chen, Y. et al. Anhydroretinol induces oxidative stress and cell death. Cancer Res 59, (1999). 3. oyos, B. et al. Activation of c-raf kinase by ultraviolet light. Regulation by retinoids. J Biol Chem 277, (2002). 4. 'Connell, M. J. et al. Retro-retinoids in regulated cell growth and death. J Exp Med 184, (1996). 5. Buck, J. et al. Anhydroretinol: a naturally occurring inhibitor of lymphocyte physiology. J Exp Med 178, (1993). 6. Um, S.-J. et al. ovel retinoic acid derivative ABP has potent inhibitory activity on cell growth and apoptosis in cancer cells. Int. J. Cancer 107, (2003). ATURE REVIEWS DRUG DISCVERY ature Publishing Group

5 7. Kaufmann, F. et al. Anti-proliferative effects of the arotinoid Ro on human cancer cells in vitro. Br. J. Cancer 67, (1993). 8. Simoni, D. et al. Programmed Cell Death (PCD) Associated with the Stilbene Motif of Arotinoids: Discovery of ovel Apoptotic Inducer Agents Possessing Activity on Multidrug Resistant Tumor Cells. Bioorg. Med. Chem. Lett. 10, (2000). 9. su, C. A. et al. Retinoid induced apoptosis in leukemia cells through a retinoic acid nuclear receptor-independent pathway. Blood 89, (1997). 10. Shao, Z. M. et al. p53 independent G0/G1 arrest and apoptosis induced by a novel retinoid in human breast cancer cells. ncogene 11, (1995). 11. Keedwell, R. G. et al. A retinoid-related molecule that does not bind to classical retinoid receptors potently induces apoptosis in human prostate cancer cells through rapid caspase activation. Cancer Res 64, (2004). 12. Cincinetti, R. et al. A ovel Atypical Retinoid Endowed with Proapoptotic and Antitumor Activity. J. Med. Chem. 46, (2003). 13. Farhana, L. et al. Apoptosis induction by a novel retinoid-related molecule requires nuclear factor-kappab activation. Cancer Res 65, (2005). 14. Dawson, M. I. et al. Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AP) family of apoptosis inducers that effectively blocks AP-induced apoptosis but not cell-cycle arrest. J Med Chem 47, (2004). 15. Bayon, Y. et al. Inhibition of IkappaB kinase by a new class of retinoid-related anticancer agents that induce apoptosis. Mol Cell Biol 23, (2003). 16. Keedwell, R. G. et al. A Retinoid-Related Molecule that Does not Bind to Classical Retinoid Receptors Potently Induces Apoptosis in uman Prostate Cancer Cells through Rapid Caspase Activation. Cancer Res. 64, (2004). 17. Kojima, S. et al. Acyclic retinoid in the chemoprevention of hepatocellular carcinoma (review). Int J ncol 24, (2004). 18. Chun, K.. et al. The synthetic heteroarotinoid SetA2 induces apoptosis in squamous carcinoma cells through a receptor-independent and mitochondria-dependent pathway. Cancer Res 63, (2003). ATURE REVIEWS DRUG DISCVERY ature Publishing Group

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