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Review

The search for new DHFR inhibitors: a review of patents, January 2001 – February 2005

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Pages 967-986 | Published online: 04 Aug 2005

Bibliography

  • SCARSELLI M, GIULIANI MM, ADU-BOBIE J: The impact of genomics on vaccine design. Trends Biotechnol (2005) 23 (2): 84–92.
  • RIDLEY RG: The need for new approaches to tropical disease: drug discovery and development for improved control strategies. In: Drugs Against Parasitic Diseases: RdD Methodologies and Issues. Fairlamb AH, Ridley RG, Vial HJ (Eds), Copyright© World Health Organization on behalf of the Special Program for Research and Training in Tropical Diseases (2003):13–21.
  • BANERJEE D, MAYER-KUCKUK P, CAPIAUX G et al.: Novel aspects of resistance to drugs targeted to dihydrofolate reductase and thymidylate synthase. Biochim. Biophys. Acta (2002) 1587:164–173.
  • VIAL HJ, RIDLEY RG, FAIRLAMB AH: Discoveries and drug development. In: Drugs Against Parasitic Diseases: RdD Methodologies and Issues. Fairlamb AH, Ridley RG, Vial HJ (Eds), Copyright© World Health Organization on behalf of the Special Program for Research and Training in Tropical Diseases (2003):5–7.
  • ••A very comprehensive review onantiparasitic drugs and on the need for control strategies.
  • BLANEY JM, HANSCH C, SILIPO C, VITTORIA A: Structure-activity relationships of dihydrofolate reductase inhibitors. Chem. Rev. (1984) 84:333–407.
  • MCINTOSH EM, HAYNES RH: dUTP pyrophosphatase as a potential target for chemotherapeutic drug development. Acta. Biochim. Pol. (1997) 44:159–171.
  • CUMMINS PL, GREATBANKS SP, RENDELL AP et al.: Computational methods for the study of enzyme reaction mechanisms 1. Application to the hydride. j. Phys. Chem. B. (2002) 106(38):9934–9944.
  • DELFINO RT, SANTOS-FILHO OA, FIGUEROA-VILLAR JD: Type 2 antifolate in the chemotherapy of fakiparum malaria. J. Braz. Chem. Soc. (2002) 13(6):727–741.
  • DA CUNHA EFF, RAIVIALHO TC, MAIA ER, DE ALENCANTRO RB: Interactions of 5-deazapteridine derivatives with Mycobacterium tuberculosis and with human dihydrofolate reductases. J. Biomol. Struct. Dynamics (2004) 22(2):119–130.
  • CUMMINS PL, GREADY JE: Energetically most likely substrate and active-site protonation sites and pathways in the catalytic mechanism of dihydrofolate reductase. J. Am. Chem. Soc. (2001) 123(15):3418–3428.
  • BERTINO JR: Karnofsky Memorial Lecture: Ode to methotrexate. J. Clin. Oncol (1993) 11:15–14.
  • COSTI MP, FERRARI S: Update on antifolate drugs targets. Curr. Drug Targets (2001) 2(2):135–166.
  • OLLIARO P: Mode of action and mechanisms of resistance for antimalarial drugs. Pharmacol Therap. (2001) 89:207-219. This paper describes how antimalarial drugs work and how resistance emerges.
  • ROSOWSKY k PT523 and other aminopterin analogs with a hemiphthaloyl-L-ornithine side chain: exceptionally tight-binding inhibitors of dihydrofolate reductase which are transported by the reduced folate carrier but cannot form polyglutamates. Curr. Med. Chem. (1999) 6:329–252.
  • ROSOWSKY A, BADER H, CUCCHI CA et al.: Methotrexate analogues. N8-Acyl-N'-(4-amino-4-deoxypteroy1)-L-ornithine derivatives: Synthesis and in vitro antitumor activity. j. Med. Chem. (1988) 31(7):1332–1337.
  • ROSOWSKY A. BADER H, FORSCH RA Synthesis of the folylpolyglutamate synthetase inhibitor N'-pteroyl-L-ornithine and its 1\18-benzoyl and N8-hemiphthaloyl derivatives, and an improved synthesis of N'-(4-amino-4-deoxypteroy1)-N8-hemiphthaloyl-L-deoxypteroy1)-N8-hemiphthaloyl-L-ornithine. Pteridines (1989) 1:91–98.
  • ROSOWSKY A, RHEE MS, GALIVAN J, WRIGHT JE: Biochemical studies on PT523, a potent nonpolyglutamatable antifolate, in cultured cells. Md. Pharmacol (1994) 45:783–791.
  • ROSOWSKY A, BADER H, WRIGHT JE et al.: Synthesis and biological-activity of N-co-hemiphthaloyl-a co-diaminoalkanoic acid anlogs of aminopterin and 3,5-dichloroaminopterin. J. Med. Chem. (1994) 37(102167–2174.
  • ROSOWSKY A, CHEN G, WRIGHT JE: Dihydrofolate reductase binding and cellular uptake of nonpolyglutamatable antifolates: correlates of cytotoxicity toward methotrexate-sensitive and -resistant human head and neck squamous carcinoma cells. Md. Pharmacol (1995) 48:758–765.
  • ROSOWSKY A, WRIGHT JE, VAIDYA CM et al: Synthesis and potent antifolate activity and cytotoxicity of B-ring deaza analogues of the nonpolyglutamatable dihydrofolate reductase inhibitor N'-(4-amino-4-deoxypteroy1)-1\18-hemiphthaloyl-L-amino-4-deoxypteroy1)-1\18-hemiphthaloyl-L-ornithine (PT523). J. Med. Chem. (1998) 41(261:5310–5319.
  • KOIZUMI S, CURT GA, FINE RL et al: Formation of methotrexate polyglutamates in purified myeloid precursor cells from normal human bone marrow. J. Clin. Invest. (1985) 75:1008–1014.
  • FRY DW, ANDERSON LA, BORST M, GOLDMAN ID: Analysis of the role of membrane transport and polyglutamylation of methotrexate in the gut and Ehrlich tumor in vivo as factors in drug sensitivity and selectivity Cancer Res. (1983) 43:1087–1092.
  • WRIGHT JE, VAIDYA CM, CHEN Y, ROSOWSKY k Efficient utilization of the reduced folate carrier in CCRF-CEM human leukemic lymphoblasts by the potent antifolate N-a-(4-amino-4-deoxypteroy1)-N-8-hemiphthaloyl-L-ornithine (PT523) and its B-ring analogues. Biochem. Pharmacol (2000) 60:41–46.
  • WRIGHT JE, YURASEK GK, CHEN Y et al.: Further studies on the interaction of nonpolyglutamatable aminopterin analogs with dihydrofolate reductase and the reduced folate carrier as determinants of in vitro antitumor activity Biochem. Pharmacol (2003) 65(9):1427–1433.
  • JACOBUS DP, JENSEN NP, AGER AL et al.: Phenoxypropoxybiguanides, prodrugs of DHFR-inhibiting diaminotriazine antimalarials. J. Med. Chem. (2001) 44(23):3925–3931.
  • ROSOWSKY A, FORSCH RA, QUEENER SF: Inhibition of Pneumocystis caring Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductases by 2,4-diamino-542-methoxy-5-(c0-carboxyalkyloxy)-benzyil pyrimidines: marked improvement in potency relative to trimethoprim and species selectivity relative to piritrexim. J. Med. Chem. (2002) 45(1):233–241.
  • ROSOWSKYA, FORSCH RA, SIBLEY CH et al.: New 2,4-diamino-5-(2',5'-substituted-benzyl)pyrimidines as potential drugs against opportunistic infections of AIDS and other immune disorders, synthesis and species-dependent antifolate activity. J. Med. Chem. (2004) 47(61:1475–1486.
  • HALLBERG A, GRAFFNER-NORDBERG M, KOLMODIN K, ÂQVIST J, QUEENER F et al: Design, synthesis, computational prediction, and biological evaluation of ester soft drugs as inhibitors of dihydrofolate reductase from Pneumocystis carinii. J. Med. Chem. (2001) 44(15):2391–2402.
  • HALLBERG A, GRAFFNER-NORDBERG M, KOLMODIN K et al: Design, synthesis, and computational affinity prediction of ester soft drugs as inhibitors of dihydrofolate reductase from Pneumocystis carinii. Eur. j Pharm. Sci. (2004) 22(1):43–53.
  • BODOR N, BUCHWALD P: Soft drug design: general principles and recent applications. Med. Res. Rev. (2000) 20:58–101.
  • RUDIN M, BECKMANN N, PORSZASZ R et al: In vivo magnetic resonance methods in pharmaceutical research: current status and perspectives. NMR Biomed. (1999) 12:69–97.
  • WOLF W, VALUCH V, PRESANT CA: Non-invasive 19F-NMRS of 5-fluorouracil in pharmacokinetics and pharmacodynamic studies. NMR Biomed. (1998) 11:380–387.
  • BORNMANN W, SPEES -WM, YANG G et al.: A fluorine-labeled methotrexate as a probe for monitoring tumor antifolate pharmacokinetics: synthesis, in vitro cytotoxicity, and pilot in vivo 19F-magnetic resonance spectra. Mol Cancer Ther. (2003) 2(10):933–939.
  • HENKIN J, WASHTIEN WL: Novel fluorinated antifolates. Enzyme inhibition and cytotoxicity studies on 2'- and 3'-fluoroaminopterin. J. Med. Chem., (1983) 26(8):1193–1196.
  • GALIVAN J, INGLESE J, MCGUIRE JJ et al.: Fluoromethotrexate: synthesis and biological activity of a potent inhibitor of dihydrofolate reductase with greatly diminished ability to form polyglutamates. Proc. Nail. Acad. Sci. USA (1985) 82:2598–2602.
  • ZOLLI-JURAN M, CECHETTO JD, HARTLEN R et al: High throughput screening identies novel inhibitors of Escherichia coli dihydrofolate reductase that are competitive with dihydrofolate. Bioorg Med. Chem. Lett. (2003) 13:2493–2496.
  • CHAN JH, HONG JS, KUYPER LF et aL:Selective inhibitors of Candida albi cans dihydrofolate reductase - activity and selectivity of 5-(arylthio)-2,4-diaminoquinazoline. J. Med. Chem. (1995) 38(18):3608–3616.
  • WHITLOW M, HOWARD AJ, STEWART D. et al: X-Ray crystal structures of Candida albicans dihydrofolate reductase: high resolution ternary complexes in which the dihydronicotinamide moiety of NADPH is displaced by an inhibitor. Med. Chem. (2001) 44:2928–2932.
  • DURAND R, SAVEL J: Dihydrofolate reductase inhibitors: new development in antiparasitic chemotherapy. Expert. Opin. Ther. Patents (2001) 11:1285-1290. This paper is an interesting review on DHFR inhibitor patents.
  • ANDERSON AC: Targeting DHFR in parasitic protozoa. Drug Discov. Today (2005) 10(2):121–128.
  • KOMPIS IM, ISLAM K, THEN RL: DNA and RNA synthesis: antifolates. Chem. Rev. (2005) 105:593–620.
  • TRAORÉ M: Role of endemic countries in research and development. In: Drugs against parasitic diseases: R&D methodologies and issues Discoveries. Vial HJ, Ridley RG, Fairlamb AH (Eds) Copyright C) World Health Organization on behalf of the Special Program for Research and Training in Tropical Diseases (2003):31–34.
  • YUVANIYAMA J et al: Insights into antifolate resistance from malarial DHFR-TS structures. Nat. Struct. Biol (2003) 10:357–365.
  • ARMSTRONG C, SMITH CC.: Cydization and N-dealkylation of chloroguanide by rabbit and rat hepatic microsomes. Toxicol Appl Pharmacol (1974) 29:90.
  • BUSHBY SRM, HITCHINGS GH: Trimethoprim, a sulphonamide potentiator. Pharmacol (1968) 33:72–90.
  • HUOVINEN P: Resistance to trimethoprim-sulfamethoxazole. Clin. Infect. Dis. (2001) 32:1608–1614.
  • ROTH B et al: 2,4-Diamino-5- entrance: benzylpyrimidines as antibacterial agents. 7. Analysis of the effect of 3,5-dialkyl substiment size and shape on binding to four different dihydrofolate reductase enzymes. J. Med. Chem. (1987) 30(2):348–356.
  • DALE GE, BROGER C, D'ARCY A et al: A single amino acid substitution in Staphylococcus aureus dihydrofolate reductase determines trimethoprim resistance. J. Mol BioL (1997) 266:23–30.
  • PIKIS A, DONKERSLOOT JA, RODRIQUEZ WJ, KEITH JM: A conservative amino acid mutation in the chromosome-encoded dihydrofolate reductase confers trimethoprim resistance in Streptococcus pneumoniae. J. Infect. Dis. (1998) 178:700–706.
  • DE GROOT R, SLUIJTER M, DE BRUYN A et al.: Genetic characterization of trimethoprim resistance in Haemophilus influenzae. Antimicrob. Agents Chemother. (1996) 40:2131–2136.
  • RAVIGLIONE MC, ZINDER DE, KOCHI k Global epidemiology of TB. Morbidity and mortality of a worldwide epidemic. JAMA (1995) 273:220–245.
  • ZHANG Y, AMZEL LM: Tuberculosis drug targets. Curr. Drug Targets (2002) 3:131–154.
  • •This paper is an excellent review on tuberculosis.
  • HUDSON A, IMAMURA T, GUTTERIDGE Wet al.: The current anti-TB drug research and development pipeline. Copyright© World Health Organization on behalf of the Special Program for Research and Training in Tropical Diseases (2003):1–44.
  • LI R, SIRAWARAPORN R, CHITNUMSUB P, SIRAWARAPORN W et al.: Three-dimensional structure of M tuberculosis dihydrofolate reductase reveals opportunities for the design of novel tuberculosis drugs. J. Mo/. Bid. (2000) 295:307–317.
  • SULING WJ, REYNOLDS RC, BARROW EW et al: Susceptibilities of Mycobacterium tuberculosis and Mycobacterium avium complex to lipophilic deazapteridine derivatives, inhibitors of dihydrofolate reductase. J. Antimicrob Chemother. (1998) 42:811–825.
  • SULING WJ, SEITZ LE, PATHAK V et al: Antimycobacterial activities of 2,4-diamino-5-deazapteridine derivatives and effects on mycobacterial dihydrofolate reductase. Antimicrob. Agents Chemother. (2000) 44(10):2784–2796.
  • SULING WJ, JOSEPH A: Maddry antimycobacterial activity of 1-deaza-7,8-dihydropteridine derivatives against Mycobacterium tuberculosis and Mycobacterium avium complex in vitro. Antimicrob. Chemother. (2001) 47(4):451.
  • HOLTJE H.-D; FOLKERS G: Molecular Modeling Basic Principles and Applications. Mannhold R, Kubinyi H, Timmerman H (Eds) VCH, Weinheim (1997).
  • HUENNEKENS FM: In search of dihydrofolate reductase. Protein Sci. (1996) 5:1201-1208. Patents

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