Organometallic nucleoside analogues with ferrocenyl linker groups: Synthesis and cancer cell line studies

Journal of Medicinal Chemistry

Volumn 57, Issue 13, 2014, Pages 5817-5822

  Nguyen, Huy V ^a   Sallustrau, Antoine ^a   Balzarini, Jan ^b   Bedford, Matthew R ^a   Eden, John C ^a   Georgousi, Niki ^a   Hodges, Nikolas J ^a   Kedge, Jonathan ^a   Mehellou, Youcef ^a   Tselepis, Chris ^a   Tucker, James H R ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1 (ALPHA CETOXYETHYL) 2 IODOFERROCENE; 1 (ALPHA HYDROXYETHYL) 2 IODOFERROCENCE; 1 (ALPHA METHOXYETHYL) 2 IODOFERROCENE; 1 (ALPHA N,N DIMETHYLAMINOETHYL) 2 IODOFERROCENE; 1 (THYMINYL)ETHYLFERROCENE; 1 ALPHA[METHYL[3 (HYDROXY)PROPYL]] 2 [(THYMINYL)ETHYL]FERROCENE; 1 [2 (ADENIN 9 YL)ETHYL]FERROCENE; 1 [ALPHA METHYL [3 (HYDROXY)PROPYL]]FERROCENE; 1 [ALPHA METHYL [3 (TERT BUTYLDIPHENYLSILYLOXY)PROPYL]] [2 (HYDROXYL)ETHYL]FERROCENE; 1 [ALPHA METHYL(2 ETHYLPROPANOATE)] 2 IODOFERROCENE; 1 [ALPHA METHYL[3 (HYDROXY)PROPYL]] 2 [2 (ADENIN 9 YL)ETHYL]FERROCENE; 1 [ALPHA METHYL[3 (TERT BUTYLDIPHENYLSILYLOXY)PROPYL]] 2 IODOFERROCENE; ALKYL GROUP; ANTINEOPLASTIC AGENT; CISPLATIN; CYTOSTATIC AGENT; FERROCENE DERIVATIVE; NUCLEIC ACID BASE; NUCLEOSIDE ANALOG; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL LINE; CHIRALITY; CONTROLLED STUDY; CYTOSTASIS; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO; HUMAN; HUMAN CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; FERROUS COMPOUNDS; HUMANS; LEUKEMIA L1210; NUCLEOSIDES; ORGANOMETALLIC COMPOUNDS;

EID: 84904289106     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500246h     Document Type: Article

References (31)

1. Galmarini, C. M.; Mackey, J. R.; Dumontet, C. Nucleoside analogues and nucleobases in cancer treatment Lancet Oncol. 2002, 3, 415
2. Cihlar, T.; Ray, A. S. Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine Antiviral Res. 2010, 85, 39
3. Romeo, G.; Chiacchio, U.; Corsaro, A.; Merino, P. Chemical synthesis of heterocyclic-sugar nucleoside analogues Chem. Rev. 2010, 110, 3337-3370
4. Mathé, C.; Périgaud, C. Recent approaches in the synthesis of conformationally restricted nucleoside analogues Eur. J. Org. Chem. 2008, 1489-1505
5. van Staveren, D. R.; Metzler-Nolte, N. Bioorganometallic chemistry of ferrocene Chem. Rev. 2004, 104, 5931-5985 (Pubitemid 40034049)
6. Fouda, M. F. R.; Abd-Elzaher, M. M.; Abdelsamaia, R. A.; Labib, A. A. On the medicinal chemistry of ferrocene Appl. Organomet. Chem. 2007, 21, 613-625 (Pubitemid 47122081)
7. Gasser, G.; Ott, I.; Metzler-Nolte, N. Organometallic anticancer compounds J. Med. Chem. 2011, 54, 3-25
8. Hillard, E. A.; Jaouen, G. Bioorganometallics: future trends in drug discovery, analytical chemistry, and catalysis Organometallics 2011, 30, 20-27
9. Dive, D.; Biot, C. Ferrocene conjugates of chloroquine and other antimalarials: the development of ferroquine, a new antimalarial ChemMedChem 2008, 3, 383-391
10. Cázares-Marinero, J. J.; Top, S.; Vessières, A.; Jaouen, G. Synthesis and antiproliferative activity of hydroxyferrocifen hybrids against triple-negative breast cancer cells Dalton Trans. 2014, 43, 817 and references therein
11. Recent review: Ornelas, C. Application of ferrocene and its derivatives in cancer research New J. Chem. 2011, 35, 1973-1985
12. Mooney, A.; Corry, A. J.; Ruairc, N.; Mahgoub, T.; O'Sullivan, D.; O'Donovan, N.; Crown, J.; Varughese, S.; Draper, S. M.; Rai, D. K.; Kenny, P. T. M. Synthesis, characterisation and biological evaluation of N -(ferrocenyl)naphthoyl amino acid esters as anticancer agents Dalton Trans. 2010, 39, 8228-8239
13. Schobert, R.; Seibt, S.; Mahal, K.; Ahmad, A.; Biersack, B.; Effenberger-Neidnicht, K.; Padhye, S.; Sarkar, F. H.; Mueller, T. Cancer selective metallocenedicarboxylates of the fungal cytotoxin illudin M J. Med. Chem. 2011, 54, 6177-6182
14. Librizzi, M.; Longo, A.; Chiarelli, R.; Amin, J.; Spencer, J.; Luparello, C. Cytotoxic effects of jay amin hydroxamic acid (JAHA), a ferrocene-based class I histone deacetylase inhibitor, on triple-negative MDA-MB231 breast cancer cells Chem. Res. Toxicol. 2012, 25, 2608-2616
15. Edwards, E. I.; Epton, R.; Marr, G. The synthesis and reactions of homonuclear ferrocene acid anhydrides and their use in the preparation of ferrocenylpenicillins and cephalosporins J. Organomet. Chem. 1979, 168, 259-272
16. Cohan, Z. H. Antibacterial and antifungal ferrocene incorporated dithiothione and dithioketone compounds Appl. Organomet. Chem. 2006, 20, 112-116
17. Patra, M.; Gasser, G.; Wenzel, M.; Merz, K.; Bandow, J. E.; Metzler-Nolte, N. Synthesis and biological evaluation of ferrocene-containing bioorganometallics inspired by the antibiotic platensimycin lead structure Organometallics 2010, 29, 4312-4219
18. Zaheer, M.; Shah, A.; Akhter, Z.; Qureshi, R.; Mirza, B.; Tauseef, M.; Bolte, M. Synthesis, characterization, electrochemistry and evaluation of biological activities of some ferrocenyl schiff bases Appl. Organomet. Chem. 2011, 25, 61-69
19. Kowalski, K.; Koceva-Chyla, A.; Pieniazek, A.; Bernasinska, J.; Skiba, J.; Rybarczyk-Pirek, J. A.; Józwiak, Z. The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates J. Organomet. Chem. 2012, 700, 58-68
20. Simenela, A. A.; Morozovaa, A. E.; Snegura, V. L.; Zykovaa, I. S.; Kachalab, V. V.; Ostrovskayac, A. L.; Bluchterovac, V. N.; Fomina, M. M. Simple route to ferrocenylalkyl nucleobases. Antitumor activity in vivo Appl. Organomet. Chem. 2009, 23, 219-224
21. Kowalski, K.; Skiba, J.; Oehninger, L.; Ott, I.; Solecka, J.; Rajnisz, A.; Therrien, B. Metallocene-modified uracils: synthesis, structure, and biological activity Organometallics. 2013, 32, 5766-5733
22. James, P.; Neudörfl, J.; Eissmann, M.; Jesse, P.; Prokop, A.; Schmalz, H.-G. Enantioselective synthesis of ferrocenyl nucleoside analogues with apoptosis-inducing activity Org. Lett. 2006, 8, 2763-2766 (Pubitemid 44085861)
23. Shago, F. R.; Swarts, C. J.; Kreft, E.; Van Rensburg, E. J. C. Antineoplastic activity of a series of ferrocene-containing alcohols Anticancer Res. 2007, 27, 3431-3434
24. Nguyen, H. V.; Sallustrau, A.; Male, L.; Thornton, P. J.; Tucker, J. H. R. 1,1′-Homodisubstituted ferrocenes containing adenine and thymine nucleobases: synthesis, electrochemistry, and formation of H-bonded arrays Organometallics 2011, 30, 5284-5290
25. Nguyen, H. V.; Zhao, Z. Y.; Sallustrau, A.; Horswell, S. L.; Male, L.; Mulas, A.; Tucker, J. H. R. A ferrocene nucleic acid oligomer as an organometallic structural mimic of DNA Chem. Commun. 2012, 48, 12165-12167
26. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. Correlation of central and planar chirality in ferrocene derivatives J. Am. Chem. Soc. 1970, 92, 5389-5393
27. Initial cell line studies indicate that 1 also displays antiviral activity (patent application GB1322752.5). Further studies are underway to establish mechanistic pathways (e.g., phosphorylation).
28. Cruickshank, K. A.; Jiricny, J.; Reese, C. B. The benzoylation of uracil and thymine Tetrahedron. Lett. 1984, 25, 681-684
29. Sallustrau, A. Synthesis of ferrocenyl derivatives as novel nucleic acid monomers. Ph.D. Thesis, University of Birmingham, U.K., 2013.
30. Locke, A. J.; Richards, C. J. Asymmetric synthesis of [3](1,1′)- and [3](1,1′)[3](3,3′)-ferrocenophanes Organometallics 1999, 18, 3750-3759
31. Barry, K. P.; Nataro, C. A new synthesis and electrochemistry of 1,1′-bis(β-hydroxyethyl)ferrocene Inorg. Chim. Acta 2009, 362, 2068-2070