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Research Paper

FR-900098, an antimalarial development candidate that inhibits the non-mevalonate isoprenoid biosynthesis pathway, shows no evidence of acute toxicity and genotoxicity

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Pages 718-728 | Received 08 Feb 2016, Accepted 24 May 2016, Published online: 22 Jun 2016

References

  • Wiesner J, Reichenberg A, Heinrich S, Schlitzer M, Jomaa H. The plastid-like organelle of apicomplexan parasites as drug target. Curr Pharm Des 2008; 14:855-71; PMID:18473835; http://dx.doi.org/10.2174/138161208784041105
  • Kuzuyama T, Shizimu T, Takahashi S, Seto H. Fosmidomycin, a specific inhibitor of 1-deoxy-d-xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway of isoprenoidbiosynthesis. Tetrahedron Lett 1998; 39:7913-6; http://dx.doi.org/10.1016/S0040-4039(98)01755-9
  • Zeidler J, Schwender J, Müller C, Wiesner J, Weidemeyer C, Beck E, Jomaa H, Lichtenthaler HK. Inhibition of the non-mevalonate 1-deoxy-D-xylulose-5-phosphate pathway of plant isoprenoid biosynthesis by fosmidomycin. Z Naturforsch C 1998; 53:980-6
  • Jomaa H, Wiesner J, Sanderbrand S, Altincicek B, Weidemeyer C, Hintz M, Türbachova I, Eberl E, Zeidler J, Lichtenthaler HK, Soldati D, Beck E. Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs. Science 1999; 285:1573-6; PMID:10477522; http://dx.doi.org/10.1126/science.285.5433.1573
  • Tahar R, Basco LK. 2007. Molecular epidemiology of malaria in Cameroon. XXV. In vitro activity of fosmidomycin and its derivatives against fresh clinical isolates of Plasmodium falciparum and sequence analysis of 1-deoxy-d-xylulose 5-phosphate reductoisomerase. Am J Trop Med Hyg 2007; 77:214-20; PMID:17690389
  • Reichenberg A, Wiesner J, Weidemeyer C, Dreiseidler E, Sanderbrand S, Altincicek B, Beck E, Schlitzer M, Jomaa H. Diaryl ester prodrugs of FR900098 with improved in vivo antimalarial activity. Bioorg Med Chem Lett 2001; 11:833-5; PMID:11277531; http://dx.doi.org/10.1016/S0960-894X(01)00075-0
  • Giessmann D, Heidler P, Haemers T, Van Calenbergh S, Reichenberg A, Jomaa H, Weidemeye C, Sanderbrand S, Wiesner J, Link A. Towards new antimalarial drugs: synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy-d-xylulose-5-phosphate reductoisomerase inhibitors. Chem Biodivers 2008; 5:643-56; PMID:18421757; http://dx.doi.org/10.1002/cbdv.200890060
  • Umeda T, Tanaka N, Kusakabe Y, Nakanishi M, Kitade Y, Nakamura KT. Molecular basis of fosmidomycin's action on the human malaria parasite Plasmodium falciparum. Sci Rep 2011; 1:9; PMID:22355528; http://dx.doi.org/10.1038/srep00009
  • Horbach S, Sahm H, Welle R. Isoprenoid biosynthesis in bacteria: two different pathways? FEMS Microbiol Lett 1993; 111:135-40; PMID:8405922; http://dx.doi.org/10.1111/j.1574-6968.1993.tb06375.x
  • Sprenger GA, Schorken U, Wiegert T, Grolle S, de Graaf AA, Taylor SV, Begley TP, Bringer-Meyer S, Sahm H. Identification of a thiamin-dependent synthase in Escherichia coli required for the formation of the 1-deoxy-d-xylulose 5-phosphate precursor to isoprenoids, thiamin, and pyridoxol. Proc Natl Acad Sci USA 1997; 94:12857-62; PMID:9371765; http://dx.doi.org/10.1073/pnas.94.24.12857
  • Okuhara M, Kuroda Y, Goto T, Okamoto M, Terano H, Kohsaka M, Aoki H, Imanaka H. Studies on new phosphonic acid antibiotics. I. FR-900098, isolation and characterization. J Antibiot (Tokyo) 1980; 33:13-7; PMID:6768704; http://dx.doi.org/10.7164/antibiotics.33.13
  • Okuhara M, Kuroda Y, Goto T, Okamoto M, Terano H, Kohsaka M, Aoki H, Imanaka H. Studies on new phosphonic acid antibiotics. III. Isolation and characterization of FR-31564, FR-32863 and FR-33289. J Antibiot (Tokyo) 1980; 33:24-8; PMID:6768705; http://dx.doi.org/10.7164/antibiotics.33.24
  • Mine Y, Kamimura T, Nonoyama S, Nishida M, Goto S, Kuwahara S. In vitro and in vivo antibacterial activities of FR-31564, a new phosphonic acid antibiotic. J Antibiot (Tokyo) 1980; 33:36-43; PMID:7372548; http://dx.doi.org/10.7164/antibiotics.33.36
  • Kuemmerle HP, Murakawa T, Soneoka K, Konishi T. Fosmidomycin: a new phosphonic acid antibiotic. Part I: Phase I tolerance studies. Int J Clin Pharmacol Ther Toxicol 1985; 23:515-20; PMID:4066075
  • Kuemmerle HP, Murakawa T, Sakamoto H, Sato N, Konishi T, De Santis F. Fosmidomycin, a new phosphonic acid antibiotic. Part II: 1. Human pharmacokinetics. 2. Preliminary early phase IIa clinical studies. Int J Clin Pharmacol Ther Toxicol 1985; 23:521-528; PMID:4066076
  • Missinou MA, Borrmann S, Schindler A, Issifou S, Adegnika AA, Matsiegui PB, Binder R, Lell B, Wiesner J, Baranek T, Jomaa H, Kremsner PG. Fosmidomycin for malaria. Lancet 2002; 360:1941-2; PMID:12493263; http://dx.doi.org/10.1016/S0140-6736(02)11860-5
  • Lell B, Ruangweerayut R, Wiesner J, Missinou MA, Schindler A, Baranek T, Hintz M, Hutchinson D, Jomaa H, Kremsner PG. Fosmidomycin, a novel chemotherapeutic agent for malaria. Antimicrob Agents Chemother 2003; 47:735-8; PMID:12543685; http://dx.doi.org/10.1128/AAC.47.2.735-738.2003
  • Lell B, Kremsner PG. Clindamycin as an antimalarial drug: review of clinical trials. Antimicrob Agents Chemother 20002; 46:2315-20; PMID:12121898; http://dx.doi.org/10.1128/AAC.46.8.2315-2320.2002
  • Borrmann S, Issifou S, Esser G, Adegnik AA, Ramharter M, Matsiegui PB, Oyakhirome S, Mawili-Mboumba PD, Missinou MA, Kun JF, et al. Fosmidomycin-clindamycin for the treatment of Plasmodium falciparum malaria. J Infect Dis 2004; 190:1534-40; PMID:15478056; http://dx.doi.org/10.1086/424603
  • Borrmann S, Lundgren I, Oyakhirome S, Impouma B, Matsiegui PB, Adegnika A, Issifou S, Kun JF, Hutchinson D, Wiesner J, et al. Fosmidomycin plus clindamycin for treatment of pediatric patients aged 1 to 14 years with Plasmodium falciparum malaria. Antimicrob Agents Chemother 2006; 50:2713-18; PMID:16870763; http://dx.doi.org/10.1128/AAC.00392-06
  • Oyakhirome S, Issifou S, Pongratz P, Barondi F, Ramharter M, Kun JF, Missinou, Lell B, Kremsner PG. Randomized controlled trial of fosmidomycin-clindamycin versus sulfadoxine-pyrimethamine in the treatment of Plasmodium falciparum malaria. Antimicrob Agents Chemother 2007; 51:1869-1871; PMID:17325227; http://dx.doi.org/10.1128/AAC.01448-06
  • Ruangweerayut R, Looareesuwan S, Hutchinson D, Chauemung A, Banmairuroi V, Na-Bangchang K. Assessment of the pharmacokinetics and dynamics of two combination regimens of fosmidomycin-clindamycin in patients with acute uncomplicated falciparum malaria. Malar J 2008; 7:225; PMID:18973702; http://dx.doi.org/10.1186/1475-2875-7-225
  • Borrmann S, Adegnika AA, Matsiegui PB, Issifou S, Schindler A, Mawili-Mboumba DP, Baranek T, Wiesner J, Jomaa H, Kremsner PG. Fosmidomycin-clindamycin for Plasmodium falciparum Infections in African children. J Infect Dis 2004; 189:901-8; PMID:14976608; http://dx.doi.org/10.1086/381785
  • Na-Bangchang K, Ruengweerayut R, Karbwang J, Chauemung A, Hutchinson D. Pharmacokinetics and pharmacodynamics of fosmidomycin monotherapy and combination therapy with clindamycin in the treatment of multidrug resistant falciparum malaria. Malar J 2007; 6:70; PMID:17531088; http://dx.doi.org/10.1186/1475-2875-6-70
  • Lanaspa M, Moraleda C, Machevo S, González R, Serrano B, Macete E, Cisteró P, Mayor A, Hutchinson D, Kremsner PG, Alonso P, Menéndez C, Bassat Q. Inadequate efficacy of a new formulation of fosmidomycin-clindamycin combination in Mozambican children less than three years old with uncomplicated Plasmodium falciparum malaria. Antimicrob Agents Chemother 2012; 56:2923-8; PMID:22430959; http://dx.doi.org/10.1128/AAC.00018-12
  • Fernandes JF, Lell B, Agnandji ST, Obiang RM, Bassat Q, Kremsner PG, Mordmüller B, Grobusch MP. Fosmidomycin as an antimalarial drug: a meta-analysis of clinical trials. Future Microbiol 2015; 10:1375-90; PMID:26228767; http://dx.doi.org/10.2217/FMB.15.60
  • Ames BN, McCann J, Yamasaki E. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutat Res 1975; 31:347-64; PMID:768755; http://dx.doi.org/10.1016/0165-1161(75)90046-1
  • Honma M, Hayashi M, Shimada H, Tanaka N, Wakuri S, Awogi T, Yamamoto KI, Kodani NU, Nishi Y, Nakadate M, Sofuni T. Evaluation of the mouse lymphoma tk assay (microwell method) as an alternative to the in vitro chromosomal aberration test. Mutagenesis 1999; 14:5-22; PMID:10474816; http://dx.doi.org/10.1093/mutage/14.1.5
  • Moore MM, Honma M, Clements J, Bolcsfoldi G, Burlinson B, Cifone M, Clarke J, Delongchamp R, Durward R, Fellows M, et al. Mouse lymphoma thymidine kinase gene mutation assay: follow-up meeting of the International Workshop on Genotoxicity Testing–Aberdeen, Scotland, 2003–Assay acceptance criteria, positive controls, and data evaluation. Environ Mol Mutagen 2006; 47(1):1-5; PMID:15991242; http://dx.doi.org/10.1002/em.20159
  • Moore MM, Honma M, Clements J, Bolcsfoldi G, Cifone M, Delongchamp R, Fellows M, Gollapudi B, Jenkinson P, Kirby P, et al. Mouse lymphoma assay workgroup. 2003. mouse lymphoma thymidine kinase gene mutation assay: international workshop on genotoxicity tests workgroup report–plymouth, UK 2002. Mutat Res 2003; 540:127-40; PMID:14550497; http://dx.doi.org/10.1016/j.mrgentox.2003.07.003
  • Storer RD, Kraynak AR, McKelvey TW, Elia MC, Goodrow TL, DeLuca JG. The mouse lymphoma L5178Y Tk+/− cell line is heterozygous for a codon 170 mutation in the p53 tumor suppressor gene. Mutat Res 1997; 373(2):157-65; PMID:9042396; http://dx.doi.org/10.1016/S0027-5107(96)00227-8
  • Hayashi M, Tice RR, MacGregor JT, Anderson D, Blakey DH, Kirsch-Volders M, Oleson FB Jr, Pacchierotti F, Romagna F, Shimada H, et al. In vivo rodent erythrocyte micronucleus assay. Mutat Res 1994; 312:293-304; PMID:7514741; http://dx.doi.org/10.1016/0165-1161(94)90039-6
  • Baumeister S, Wiesner J, Reichenberg A, Hintz M, Bietz S, Harb OS, Roos DS, Kordes M, Friesen J, Matuschewski K, et al. Fosmidomycin uptake into Plasmodium and Babesia-infected erythrocytes is facilitated by parasite-induced new permeability pathways. PLoS One 2011; 6:e19334; PMID:21573242; http://dx.doi.org/10.1371/journal.pone.0019334
  • Kamiya T, Hashimoto M, Hemmi K, Takeno H. Hydroxyaminohydrocarbon-phosphonic acids. Fujisawa Pharmaceutical Co. Ltd. U.S. Patent Application No. 4,206,156, 3 June 1980.
  • Öhler E, Kanzler S. Regioselective palladium(0) catalyzed amination of carbonates of allylic a-hydroxyphosphonates with hydroxylamine derivatives: A convenient route to phosphonic acids related to the antibiotic fosmidomycin. Synthesis 1995;539-43
  • Maron DM, Ames BN. Revised methods for the Salmonella mutagenicity test. Mutat Res 1983; 113:173-215; PMID:6341825; http://dx.doi.org/10.1016/0165-1161(83)90010-9
  • Clive D, Spector JF. Laboratory procedure for assessing specific locus mutations at the TK locus in cultured L5178Y mouse lymphoma cells. Mutat Res 1975; 31:17-29; PMID:1093012; http://dx.doi.org/10.1016/0165-1161(75)90059-X
  • Schmid W. The micronucleus test for cytogenetic analysis. In Chemical mutagens, principle and methods for their detection A. Hollaender (ed.), vol. 1. Plenum Press: New York, NY. 1976; pp. 31-53.
  • Heddle JA, Stuart E, Salamone MF. 1984. The bone marrow micronucleus test, In G. J. Kilbey, et al. (ed.) Handbook of mutagenicity test procedures, 2nd ed. Elsevier: Amsterdam. p. 441-457.
  • Mavournin KH, Blakey DH, Cimino MC, Salamone MF, Heddle JA. The in vivo micronucleus assay in mammalian bone marrow and peripheral blood. A report of the U.S. environmental protection agency gene-tox program. Mutat Res 1990; 239:29-80; PMID:2195332; http://dx.doi.org/10.1016/0165-1110(90)90030-F