Full-text resources of PSJD and other databases are now available in the new Library of Science.
Visit https://bibliotekanauki.pl

PL EN


Preferences help
enabled [disable] Abstract
Number of results
2014 | 61 | 4 | 651-654

Article title

Organometallic iron complexes as potential cancer therapeutics

Content

Title variants

Languages of publication

EN

Abstracts

EN
Metal-containing drugs have long been used for medicinal purposes in more or less empirical way. The potential of these anticancer agents has only been fully realised and explored since the discovery of the biological activity of cisplatin. Cisplatin and carboplatin have been two of the most successful anti-cancer agents ever developed, and are currently used to treat ovarian, lung and testicular cancers. They share certain side effects, so their clinical use is severely limited by dose-limiting toxicity. Inherent or acquired resistance is a second problem often associated with platinum-based drugs, with further limits of their clinical use. These problems have prompted chemists to employ different strategies in development of the new metal-based anticancer agents with different mechanisms of action. There are various metal complexes still under development and investigation for the future cancer treatment use. In the search for novel bio-organometallic molecules, iron containing anti-tumoral agents are enjoying an increasing interest and appear very promising as the potential drug candidates. Iron, as an essential cofactor in a number of enzymes and physiological processes, may be less toxic than non essential metals, such as platinum. Up to now, some of iron complexes have been tested as cytotoxic agents and found to be endowed with an antitumor activity in several in vitro tests (on cultured cancer cell lines) and few in vivo experiments (e. g. on Ehrlich's ascites carcinoma). Although the precise molecular mechanism is yet to be defined, a number of observations suggest that the reactive oxygen species can play important role in iron-induced cytotoxicty. This review covers some relevant examples of research on the novel iron complexes.

Year

Volume

61

Issue

4

Pages

651-654

Physical description

Dates

published
2014
received
2014-02-18
revised
2014-10-26
accepted
2014-12-03
(unknown)
2014-12-19

Contributors

  • Department of Experimental Medicine, Faculty of Medicine, P. J. Šafárik University, Košice, Slovak Republic
author
  • Department of Pharmacology, Faculty of Medicine, P. J. Šafárik University, Košice, Slovak Republic
  • Department of Medical and Clinical Biochemistry and LABMED, Faculty of Medicine, P. J. Šafárik University, Košice, Slovak Republic

References

  • Abu-Surrah AS, Kettunen M (2006) Platinum group antitumor chemistry: design and development of new anticancer drugs complementary to cisplatin. Curr Med Chem 13: 1337-1357.
  • Acevedo-Morantes CY, Meléndez E, Singh SP, Ramírez-Vick JE (2012) Cytotoxicity and reactive oxygen species generated by ferrocenium and ferrocene on MCF7 and MCF10A cell lines. J Cancer Sci Ther 4: 271-275.
  • Al-Bari MA, Hossen MF, Khan A, Islam MR, Kudrat-E-Zahan M, Mosaddik MA, Zakaria CM, Islam MA (2007) In vitro antimicrobial and cytotoxic activities of ferrocene derivative compounds.Pak J Biol Sci 10: 2423-2429.
  • Allardyce CS, Dorcier A, Scolaro C, Dyson PJ (2005) Development of organometallic (organo-transition metal) pharmaceuticals. Appl Organomet Chem 19: 1-10.
  • Anisimov VN, Sikora E, Pawelec G (2009) Relationships between cancer and aging: a multilevel approach. Biogerontology 10: 323-338.
  • Belmont P, Bosson J, Godet T, Tiano M (2007) Acridine and acridone derivatives, anticancer properties and synthetic methods: where are we now? Anticancer Agents Med Chem 7: 139-169.
  • Bray F, Moller B (2006) Predicting the future burden of cancer. Nat Rev Cancer 6: 63-74.
  • Desoize B (2004) Metals and metal compounds in cancer treatment. Anticancer Res 24: 1529-1544.
  • Dombrowski KE, Baldwin W, Sheats JE (1986) Metallocenes in biochemistry, microbiology and medicine. J Organomet Chem 302: 281-306.
  • Ferreira AP, da Silva JLF, Duarte MT, da Piedade MFM, Robalo MP, Harjivan SG, Marzano C, Gandin V, Marques MM (2009) Synthesis and characterization of new organometallic benzo[b]thiophene derivatives with potential antitumor properties. Organometallics 28: 5412-5423.
  • Fiorina VJ, Dubois RJ, Brynes S (1978) Ferrocenyl polyamines as agents for the chemoimmunotherapy of cancer. J Med Chem 21: 393-395.
  • Flajsig I, Poljak-Blazi M (1990) Influence of iron on proliferation and cell cycle kinetics on cultured malignant and nonmalignant cells. Oncology 47: 443-446.
  • Fouda MFR, Abd-Elzaher MM, Abdelsamaia RA, Labib AA (2007) On the medicinal chemistry of ferrocene. Appl Organomet Chem 21: 613-625.
  • Franke JC, Plötz M, Prokop A, Geilen CC, Schmalz HG, Eberle J (2010) New caspase-independent but ROS-dependent apoptosis pathways are targeted in melanoma cells by an iron-containing cytosine analogue. Biochem Pharmacol 79: 575-586.
  • Galluzzi L, Senovilla L, Vitale I, Michels J, Martins I, Kepp O, Castedo M, Kroemer G (2012) Molecular mechanisms of cisplatin resistance. Oncogene 31: 1869-1883.
  • Gasser G, Ott I, Metzler-Nolte N (2011) Organometallic anticancer compounds. J Med Chem 54: 3-25.
  • Gottesman MM (2002) Mechanisms of cancer drug resistance. Annu Rev Med 53: 615-627.
  • Hajdu SI (2011) A note from history: landmarks in history of cancer, part 1. Cancer 117: 1097-1102.
  • Hamels D, Dansette PM, Hillard EA, Top S, Vessières A, Herson P, Jaouen G, Mansuy D (2009) Ferrocenyl quinone methides as strong antiproliferative agents: formation by metabolic and chemical oxidation of ferrocenyl phenols. Angew Chem Int Ed Engl 48: 9124-9126.
  • Hillard E, Vessières A, Thouin L, Jaouen G, Amatore C (2005) Ferrocene-mediated proton-coupled electron transfer in a series of ferrocifen-type breast-cancer drug candidates. Angew Chem Int Ed Engl 45: 285-290.
  • Hillard EA, Pigeon P, Vessières A, Amatore C, Jaouen G (2007) The influence of phenolic hydroxy substitution on the electron transfer and anti-cancer properties of compounds based on the 2-ferrocenyl-1-phenyl-but-1-ene motif. Dalton Trans 43: 5073-5081.
  • Hirschhäuser C, Velcicky J, Schlawe D, Hessler E, Majdalani A, Neudörfl JM, Prokop A, Wieder T, Schmalz HG (2013) Nucleoside analogues with a 1,3-diene-Fe(CO)3 substructure: stereoselective synthesis, configurational assignment, and apoptosis-inducing activity. Chem Eur J 19: 13017-13029.
  • Chen D, Milacic V, Frezza M, Dou QP (2009) Metal complexes, their cellular targets and potential for cancer therapy. Curr Pharm Des 15: 777-791.
  • Jaouen G, Top S, Vessières A, Leclercq G, McGlinchey MJ (2004) The first organometallic selective estrogen receptor modulators (SERMs) and their relevance to breast cancer.Curr Med Chem 11: 2505-2517.
  • Jemal A, Bray F, Center MM, Ferlay J, Ward E, Forman D (2011) Global cancer statistics. CA Cancer J Clin 61: 69-90.
  • Jungwirth U, Kowol CR, Keppler BK, Hartinger CG, Berger W, Heffeter P (2011) Anticancer activity of metal complexes: involvement of redox processes. Antioxid Redox Signal 15: 1085-1127.
  • Kelland LR (2000) Preclinical perspectives on platinum resistance. Drugs 59: 1-8.
  • Köpf-Maier P, Köpf H, Neuse EW (1984) Ferrocenium salts; the first antineoplastic iron compounds. Angew Chem Int Ed Engl 23: 456-457.
  • Lu C, Heldt JM, Guille-Collignon M, Lemaître F, Jaouen G, Vessières A, Amatore C (2014) Quantitative analyses of ROS and RNS production in breast cancer cell lines incubated with ferrocifens. Chem Med Chem 9: 1286-1293.
  • Marzano C, Pellei M, Tisato F, Santini C (2009) Copper complexes as anticancer agents. Anticancer Agents Med Chem 9: 185-211.
  • Meggers E (2007) Exploring biologically relevant chemical space with metal complexes. Curr Opin Chem Biol 11: 287-292.
  • Michard Q, Jaouen G, Vessieres A, Bernard BA (2008) Evaluation of cytotoxic properties of organometallic ferrocifens on melanocytes, primary and metastatic melanoma cell lines. J Inorg Biochem 102: 1980-1985.
  • Mojzisova G, Mojzis J, Mirossay L, Vaskova J, Perjesi P, Bomba A (2014) Novel ferrocenyl chalcones as potential cancer therapeutics. Anticancer Res 34: 6065.
  • Monserrat JP, Tiwari KN, Quentin L, Pigeon P, Jaouen G, Vessières, A., Chabot GG, Hillard EA (2013) Ferrocenyl flavonoid-induced morphological modifications of endothelial cells and cytotoxicity against B16 murine melanoma cells. J Organomet Chem 734: 78-85.
  • Nguyen HV, Sallustrau A, Balzarini J, Bedford MR, Eden JC, Georgousi N, Hodges NJ, Kedge J, Mehellou Y, Tselepis C, Tucker JH (2014) Organometallic nucleoside analogues with ferrocenyl linker groups: synthesis and cancer cell line studies. J Med Chem 57: 5817-5822.
  • Ong CW, Jeng JY, Juang SS, Chen CF (1992) A ferrocene-intercalator conjugate with a potent cytotoxicity. Bioorg Med Chem Lett 2: 929-932.
  • Osella D, Ferrali M, Zanello P, Laschi F, Fontani M, Nervi C, Cavigiolio G (2000) On the mechanism of the antitumor activity of ferrocenium derivatives. Inorg Chim Acta 306: 42-48.
  • Ott I, Gust R (2007) Non platinum metal complexes as anti-cancer drugs. Arch Pharm (Weinheim) 340: 117-126.
  • Pan H, Mukhopadhyay P, Rajesh M, Patel V, Mukhopadhyay B, Gao B, Haskó G, Pacher P (2009) Cannabidiol attenuates cisplatin-induced nephrotoxicity by decreasing oxidative/nitrosative stress, inflammation, and cell death. J Pharmacol Exp Ther 328: 708-714.
  • Poljak-Blazi M, Kralj M, Hadzija MP, Zarković N, Zarković K, Waeg G (2000) Involvement of lipid peroxidation, oncogene expression and induction of apoptosis in the antitumorous activity of ferric-sorbitol-citrate. Cancer Biother Radiopharm 15: 285-293.
  • Quirante J, Dubar F, González A, Lopez C, Cascante M, Cortés R, Forfar I, Pradines B, Biot C (2011) Ferrocene-indole hybrids for cancer and malaria therapy. J Organomet Chem 696: 1011-1017.
  • Rafique S, Idrees M, Nasim A, Kabar H, Athar A (2010) Transition metal complexes as potential therapeutic agents. Biotechnol Mol Biol Rev 5: 38-45.
  • Simenel AA, Morozova EA, Snegur LV, Zykova SI, Kachala VV, Ostrovskaya LA, Bluchterova NV, Fomina MM (2009) Simple route to ferrocenylalkyl nucleobases. Antitumor activity in vivo. Appl Organomet Chem 23: 219-224.
  • Skiba J, Rajnisz A, de Oliveira KN, Ott I, Solecka J, Kowalski K (2012) Ferrocenyl bioconjugates of ampicillin and 6-aminopenicillinic acid - synthesis, electrochemistry and biological activity. Eur J Med Chem 57: 234-239.
  • Top S, Thibaudeau C, Vessieres A, Brule E, Le Bideau F, Joerger JM, Plamont MA, Samreth S, Edgar A, Marrot J, Herson P, Jaouen G (2009) Synthesis and structure activity relationship of organometallic steroidal androgen derivatives. Organometallics 28: 1414-1424.
  • Woldemariam GA, Mandal SS (2008) Iron(III)-salen damages DNA and induces apoptosis in human cell via mitochondrial pathway. J Inorg Biochem 102: 740-747.
  • Wong ELM, Fang GS, Che CM, Zhu N (2005) Highly cytotoxic iron(II) complexes with pentadentate pyridyl ligands as a new class of anti-tumor agents. Chem Commun 36: 4578-4580.
  • Yeary RA (1969) Chronic toxicity of dicyclopentadienyliron (ferrocene) in dogs. Toxicol Appl Pharmacol 15: 666-676.
  • Zhivkova T, Kalfin R, Drakova L, Leventieva-Necheva E, Mosoarca EM, Tudore R, Costisor O, Alexandrova R (2010) Influence of newly synthesized mixed ligand iron complexes on viability and proliferation of tumor cells. Trakia J Sci 8: 73-77.

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.bwnjournal-article-abpv61p651kz
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.