Synthesis and Characterization of Ferrocene Acetals and Evaluation of Their Antineoplastic Properties by Using Breast Cancer Cell Lines In Vitro

To Dr. Scott E. Denmark in his 60^th birthday’s celebration. With gratitude and best wishes from Dr. Mirna Rivera Claudio.

Abstract

Two new ferrocene acetals were synthesized from a chiral diol in toluene and characterized by a range of spectroscopic techniques. The biological activities of the products were evaluated by using the breast adenocarcinoma cell lines T47D, MCF7, ZR-75-1, MD-MB-468, and MD-MB-231. In comparison with tamoxifen, the ferrocene acetals showed moderate anticancer activity in vitro for the T47D and MCF7 cell lines.

Key words

acetals - organometallic compounds - iron - drugs

• References

• 1 Current address: J. Santiago-Ofarril, Department of Pediatrics Research, The University of Texas MD Anderson Cancer Center, The University Graduate Biomedical Sciences at Houston, Houston TX, USA.
• 2a Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. Togni A, Hayashi T. Wiley-VCH; Weinhem: 1995
• 2b Jaouen G. Bioorganometallics . Wiley-VCH; Weinheim: 2005
• 2c Štěpnička P. Ferrocenes: Ligands, Materials and Biomolecules. Wiley; Chichester: 2008
• 2d Maree MD, Neuse EW, Erasmus E, Swarts JC. Metal-Based Drugs 2008; 217573
• 2e Shago RF, Swarts JC, Kreft E, Van Rensburg CE. J. Anticancer Res. 2007; 27: 3431
• 2f Chekhun VF, Kulik GI, Yurchenko OV, Tryndyak VP, Todor IN, Luniv LS, Tregubova NA, Pryzimirska TV, Montgomery B, Rusetskaya NV, Pogribny IP. Cancer Lett. 2006; 231: 87
• 2g Likhite VS, Stossi F, Kim K, Katzenellenbogen BS, Katzenellenbogen JA. Mol. Endocrinol. 2006; 20: 3120
• 2h Vessières A, Corbet C, Heldt JM, Lories N, Jouy N, Laïos I, Leclerq G, Jaouen G, Toillon RA. J. Inorg. Biochem. 2010; 104: 503
• 2i Michard Q, Jaouen G, Vessieres A, Bernard BA. J. Inorg. Biochem. 2008; 102: 1980
• 2j Bruijnincx PC. A, Sadler PJ. Curr. Opin. Chem. Biol. 2008; 12: 197
• 2k Wei CW, Peng Y, Zhang L, Huang Q, Cheng M, Liu YN, Li J. Bioorg. Med. Chem. Lett. 2011; 21: 5818
• 3 Riant O, Samuel O, Kagan HB. J. Am. Chem. Soc. 1993; 115: 5835
• 4 Hua DH, Lagneau NM, Chen Y, Robben PM, Clapham G, Robinson PD. J. Org. Chem. 1996; 61: 4508
• 5 Jiang Q, Zhong Q, Zhang Q, Zheng S, Wang G. ACS Med. Chem. Lett. 2012; 3: 392
• 6 Trivedi R, Deepthi SB, Giribabu L, Sridhar B, Sujitha P, Kumar CG, Ramakrishna KV. S. Eur. J. Inorg. Chem. 2012; 2267
• 7a National Cancer Institute. www.cancer.gov/cancertopics/ understandingcancer/estrogenreceptors (accessed May 2013).
• 7b Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, Agard DA. Cell 1998; 95: 927
• 7c Qadir MA, Kwok B, Dragowska WH, To KH, Le D, Bally MB, Gorski SM. Breast Cancer Res. Treat. 2008; 112: 389
• 8 Yamaguchi Y, Ding W, Sanderson CT, Borden ML, Morgan MJ, Kutal C. Coord. Chem. Rev. 2007; 251: 515
• 9 Mamane V, Ledoux-Rak I, Deveau S, Zyss J, Riant O. Synthesis 2003; 317