Synthesis, in vitro antiplasmodial and antiproliferative activities of a series of quinoline-ferrocene hybrids

Medicinal Chemistry Research

Volumn 23, Issue 3, 2014, Pages 1214-1224

  N'Da, David D ^a   Smith, Peter J ^b  

^a NORTH WEST UNIVERSITY   (South Africa)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Cancer; Etoposide; Ferrocene; Hybrids; Malaria; Quinoline

Indexed keywords

EID: 84893754795     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0748-4     Document Type: Article

References (46)

1. 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
2. Atwell GJ, Bos CD, Baguley BC, Denny WA (1988) Potential antitumor agents. 56. "Minimal" DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides. J Med Chem 31:1048-1052
3. Barends M, Jaidee A, Khaohirun N, Singhasivanon P, Nosten F (2007) In vitro activity of ferroquine (SSR 97193) against Plasmodium falciparum isolates from the Thai-Burmese border. Malar J 6:81
4. Barnes KR, Lippard SJ (2004) Cisplatin and related anticancer drugs: recent advances and insights. Met Ions Biol Syst 42:143-177
5. Beqa L, Fan Z, Singh AK, Senapati D, Ray PC (2011) Gold nano popcorn attached SWCNT hybrid nanomaterial for targeted diagnosis and photothermal therapy of human breast cancer cells. ACS Appl Mater Interfaces 3:3316-3324
6. Biot C, Dessolin J, Ricard I, Dive D (2004) Easily synthesized antimalarial ferrocene triazacyclononane quinoline conjugates. J Organomet Chem 689:4678-4682
7. Biot C, Daher W, N'Diaye CM, Melnyk P, Pradines B, Chauvain N, Pellet A, Fraisse L, Pelinski L, Jarry C, Brocard J, Khalife J, Forfar-Bares I, Dive D (2006) Probing the role of the covalent linkage of ferrocene into a chloroquine template. J Med Chem 49:4707-4714
8. Biot C, Chavain N, Dubar F, Pradines B, Trivelli X, Brocard J, Forfar I, Dive D (2009) Structure-activity relationships of 4-N-substituted ferroquine analogues. Time to re-evaluate the mechanism of action of ferroquine. J Organomet Chem 694:845-854
9. Biot C, Nosten F, Fraisse L, Ter-Minassian D, Khalife J, Dive D (2011) The antimalarial ferroquine: from bench to clinic. Parasite 18:207-214
10. Biot C, Castro W, Botté CY, Navarro M (2012) The therapeutic potential of metal-based antimalarial agents: implications for the mechanism of action. Dalton Trans 41:6335-6349
11. Blagbrough IS, Carrington S, Geall AJ (1997) Polyamines and polyamine amides as potent selective receptor probes, novel therapeutic lead compounds and synthetic vectors in gene therapy. Pharm Sci 3:223-233
12. Chavain N, Vezin H, Dive D, Touati N, Paul JP, Buisine E, Biot C (2008) Investigation of the redox behavior of ferroquine, a new antimalarial. Mol Pharm 5:710-716
13. Cloete TT, Krebs HJ, Clark JA, Connelly MC, Orcutt A, Sigal MS, Guy RK, N'Da DD (2013) Synthesis, antimalarial activity and cytotoxicity of 10-aminoethylether derivatives of artemisinin. Bioorg Chem 46:10-16
14. Daher W, Biot C, Fandeur T, Jouin H, Pelinski L, Viscogliosi E, Fraisse L, Pradines B, Brocard J, Khalife J, Dive D (2006) Assessment of Plasmodium falciparum resistance to ferroquine (SSR97193) in field isolates and in W2 strain under pressure. Malar J 5:11
15. Dondorp AM, Nosten F, Yi P, Das D, Phyo AP, Tarning J, Lwin KM, Ariey F, Hanpithakpong W, Lee SJ, Ringwald P, Silamut K, Imwong M, Chotivanich K, Lim P, Herdman T, An SS, Yeung S, Singhasivanon P, Day NP, Lindegardh N, Socheat D, White NJ (2009) Artemisinin resistance in Plasmodium falciparum malaria. N Engl J Med 361:455-467
16. Dubar F, Egan TJ, Pradines B, Kuter D, Ncokazi KK, Forge D, Paul JF, Pierrot C, Kalamou H, Khalife J, Buisine E, Rogier C, Vezin H, Forfar I, Slomianny C, Trivelli X, Kapishnikov S, Leiserowitz L, Dive D, Biot C (2011) The antimalarial ferroquine: role of the metal and intramolecular hydrogen bond in activity and resistance. ACS Chem Biol 6:275-287
17. Hocart SJ, Liu H, Deng H, De D, Krogstad FM, Krogstad DJ (2011) 4-Aminoquinolines active against chloroquine-resistant Plasmodium falciparum: basis of antiparasite activity and quantitative structure-activity relationship analyses. Antimicrob Agents Chemother 55:2233-2244
18. Hottin A, Dubar F, Steenackers A, Delannoy P, Biot C, Behr JB (2012) Iminosugar-ferrocene conjugates as potential anticancer agents. Org Biomol Chem 10:5592-5597 http://clinicaltrials.gov/ct2/show/ NCT00988507
19. Kelland LR, Sharp SY, O'Neill CF, Raynaud FI, Beale PJ, Judson IR (1999) Glutathione induces cellular resistance against cationic dinuclear platinum anticancer drugs. J Inorg Biochem 77:111-115
20. Köpf-Maier P, Köpf H, Neuse EW (1984) Ferricenium complexes: a new type of water-soluble antitumor agent. J Cancer Res Clin Oncol 108:336-340
21. Kumar K, Singh P, Kremer L, Guérardel Y, Biot C, Kumar V (2012) Synthesis and in vitro anti-tubercular evaluation of 1,2,3-triazole tethered β-lactam-ferrocene and β-lactam-ferrocenylchalcone chimeric scaffolds. Dalton Trans 41:5778-5781
22. Kumar K, Carrère-Kremer S, Kremer L, Guérardel Y, Biot C, Kumar V (2013) Azide-alkyne cycloaddition en route towards 1H-1,2,3-triazole- tethered β-lactam-ferrocene and β-lactam-ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation. Dalton Trans 42:1492-1500
23. Lal B, Badshah A, Altaf AA, Tahir MN, Ullah S, Huq F (2012) Synthesis, characterization and antitumor activity of new ferrocene incorporated N, N'-disubstituted thioureas. Dalton Trans 41:14643-14650
24. Leimanis ML, Jaidee A, Sriprawat K, Kaewpongsri S, Suwanarusk R, Barends M, Phyo AP, Russell B, Renia L, Nosten F (2010) Plasmodium vivax susceptibility to ferroquine. Antimicrob Agents Chemother 54:2228-2230
25. Mahajan A, Kremer L, Louw S, Guérardel Y, Chibale K, Biot C (2011) Synthesis and in vitro antitubercular activity of ferrocene-based hydrazones. Bioorg Med Chem Lett 21:2866-2868
26. Makler MT, Ries JM, Williams JA, Bancroft JE, Peper RC, Gibbins BL, Hinrichs DJ (1993) Parasite lactate dehydrogenase as an assay for Plasmodium falciparum drug sensitivity. Am Soc Trop Med Hyg 48:739-741
27. Matos J, Vale N, Collins MS, Gut J, Rosenthal PJ, Cushion MT, Moreira R, Paula Gomes (2010) PRIMACENES: novel non-cytotoxic primaquine-ferrocene conjugates with anti-Pneumocystis carinii activity. MedChemComm 1:199-201
28. Mcfadyen WD, Denny WA, Wakelin LPG (1988) Alkyl-linked diquinolines are monofunctional AT-selective DNA-intercalating agents. FEBS Lett 228:235-240
29. Mosmann TJ (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Immunol 65:55-63
30. Muller O, Sie A, Meissner P, Schirmer RH, Kouyate B (2009) Artemisinin resistance on the Thai-Cambodian border. Lancet 374:1419
31. N'Da DD, Breytenbach JC, Smith PJ, Lategan C (2010) Synthesis, cytotoxicity and antimalarial activity of ferrocenyl amides of 4-aminoquinolines. ArzneimForsch-DrugRes 60:627-635
32. N'Da DD, Breytenbach JC, Smith PJ, Lategan C (2011) Synthesis and antiplasmodial activity of quinoline-ferrocene esters. ArzneimForsch-DrugRes 61:358-365
33. Noedl H, Se Y, Sriwichai S, Schaecher K, Teja-Isavadharm P, Smith B, Rutvisuttinunt W, Bethell D, Surasri S, Fukuda MM, Socheat D, Chan TL (2010) Artemisinin resistance in Cambodia: a clinical trial designed to address an emerging problem in Southeast Asia. Clin Infect Dis 51:e82-e89
34. Petersen I, Eastman R, Lanzer M (2011) Drug-resistant malaria: molecular mechanisms and implications for public health. FEBS Lett 585:1551-1562
35. Phyo AP, Nkhoma S, Stepniewska K, Ashley EA, Nair S, Mcgready R, Moo CL, Al-saai S, Dondorp AM, Lwin KM, Singhasivanon P, Day NPJ, White NJ, Anderson TJC, Nosten F (2012) Emergence of artemisinin-resistant malaria on the western border of Thailand: a longitudinal study. Lancet 379:1960-1966
36. 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 Organometal Chem 696:1011-1017
37. Roux C, Biot C (2012) Ferrocene-based antimalarials. Future. Med Chem 4:783-797
38. Rubinstein LV, Shoemaker RH, Paull KD, Simon RM, Tosini S, Skehan P, Scudiero DA, Monks A, Boyd MRJ (1990) Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. Natl Cancer Inst 82:1113-1117
39. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107-1112
40. Supan C, Mombo-Ngoma G, Dal-Bianco MP, Ospina-Salazar CL, Issifou S, Mazuir F, Filali-Ansary A, Biot C, Ter-Minassian D, Ramharter M, Kremsner PG, Lell B (2012) Pharmacokinetics of ferroquine, a novel 4-aminoquinoline, in asymptomatic carriers of Plasmodium falciparum infections. Antimicrob Agents Chemother 56:3165-3173
41. Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science 193:673-675
42. van Heerden L, Cloete TT, Breytenbach JW, de Kock C, Smith PJ, Breytenbach JC, N'Da DD (2012) Synthesis and in vitro antimalarial activity of a series of bisquinoline and bispyrrolo[1,2a]quinoxaline compounds. Eur J Med Chem 55:335-345
43. WHO (2012); http://www.who.int/mediacentre/factsheets/fs094/en/index.html
44. WHO (World Health Organization) (2011) World malaria report
45. Wu C-C, Li T-K, Farh L, Lin L-Y, Lin T-S, Yu Y-J, Yen T-J, Chiang C-W, Chan N-L (2011) Structural basis of type II topoisomerase inhibition by the anticancer drug etoposide. Science 333:459-462
46. Zhou B, Li J, Feng BJ, Ouyang Y, Liu YN, Zhou F (2012) Syntheses and in vitro antitumor activities of ferrocene-conjugated Arg-Gly-Asp peptides. J Inorg Biochem 116:19-25