메뉴 건너뛰기




Volumn 6, Issue 1, 2012, Pages 15-25

Comparative analysis of in vitro rat liver metabolism of the antimalarial primaquine and a derived imidazoquine

Author keywords

Drug metabolism; Imidazoquines; Malaria; Microsomes; Peptidomimetic; Primaquine; Vivax

Indexed keywords

IMIDAZOQUINE; PRIMAQUINE; PRIMAQUINE DERIVATIVE; UNCLASSIFIED DRUG; ANTIMALARIAL AGENT; DRUG DERIVATIVE; IMIDAZOLIDINE DERIVATIVE;

EID: 84864935570     PISSN: 18723128     EISSN: None     Source Type: Journal    
DOI: 10.2174/187231212800229273     Document Type: Article
Times cited : (4)

References (60)
  • 1
    • 60549099364 scopus 로고    scopus 로고
    • Primaquine revisited: Six decades after its discovery
    • Vale, N.; Moreira, R.; Gomes, P. Primaquine revisited: six decades after its discovery, Eur. J. Med. Chem., 2009, 44, 937-953.
    • (2009) Eur. J. Med. Chem , vol.44 , pp. 937-953
    • Vale, N.1    Moreira, R.2    Gomes, P.3
  • 2
    • 0036592710 scopus 로고    scopus 로고
    • Short report: Therapeutic efficacy of chloroquine combined with primaquine against Plasmodium falciparum in northeastern Papua, Indonesia
    • Baird, J.K.; Wiady, I.; Sutanihardja, A.; Suradi; Purnmo; Basri, H.; Sekartuti; Ayomi, E.; Fryauff, D.J.; Hoffman, S.L. Short report: therapeutic efficacy of chloroquine combined with primaquine against Plasmodium falciparum in northeastern Papua, Indonesia. Am. J. Trop. Med. Hyg., 2002, 66, 659-660.
    • (2002) Am. J. Trop. Med. Hyg , vol.66 , pp. 659-660
    • Baird, J.K.1    Wiady, I.2    Sutanihardja, A.3    Suradi4    Purnmo5    Basri, H.6    Sekartuti7    Ayomi, E.8    Fryauff, D.J.9    Hoffman, S.L.10
  • 4
    • 0442307497 scopus 로고    scopus 로고
    • Antimalarial drug toxicity: A review
    • Taylor, W.R.; White, N.J. Antimalarial drug toxicity: a review, Drug Saf., 2004, 27, 25-61.
    • (2004) Drug Saf , vol.27 , pp. 25-61
    • Taylor, W.R.1    White, N.J.2
  • 7
    • 0014425983 scopus 로고
    • Methemoglobinemia provoked by antimalarial chemoprophylaxis in Vietnam
    • Cohen, R.J.; sachs, J.R.; Wicker, D.J.; Contrad, M.E.; Methemoglobinemia provoked by antimalarial chemoprophylaxis in Vietnam, N. Engl. J. Med., 1968, 279, 1127-1131.
    • (1968) N. Engl. J. Med , vol.279 , pp. 1127-1131
    • Cohen, R.J.1    Sachs, J.R.2    Wicker, D.J.3    Contrad, M.E.4
  • 8
    • 0029945526 scopus 로고    scopus 로고
    • Drug-induced methemoglobinemia. Treatment issues
    • Coleman, M.D.; Coleman, N.A., Drug-induced methemoglobinemia. Treatment issues. Drug Saf. 1996, 14, 394-405.
    • (1996) Drug Saf , vol.14 , pp. 394-405
    • Coleman, M.D.1    Coleman, N.A.2
  • 11
    • 0032781772 scopus 로고    scopus 로고
    • Metabolism of primaquine by liver homogenate fractions. Evidence for monoamine oxidase and cytochrome P450 involvement in the oxidative deamination of primaquine to carboxyprimaquine
    • Constantino, L.; Paixão, P.; Moreira, R.; Portela, M.J.; Do Rosário, V.E.; Iley, J. Metabolism of primaquine by liver homogenate fractions. Evidence for monoamine oxidase and cytochrome P450 involvement in the oxidative deamination of primaquine to carboxyprimaquine. Exp. Toxicol. Pathol., 1999, 51, 299-303.
    • (1999) Exp. Toxicol. Pathol , vol.51 , pp. 299-303
    • Constantino, L.1    Paixão, P.2    Moreira, R.3    Portela, M.J.4    Do Rosário, V.E.5    Iley, J.6
  • 12
    • 0021229470 scopus 로고
    • Pharmacokinetic of primaquine in man: Identification of the carboxylic acid derivative as a major plasma metabolite
    • Mihaly, G.W.; Ward, S.A.; Edwards, G.; L'E Orme, M.; Breckenridge, A.M. Pharmacokinetic of primaquine in man: identification of the carboxylic acid derivative as a major plasma metabolite. Braz. J. Clin. Pharmacol. 1984, 17, 441-446.
    • (1984) Braz. J. Clin. Pharmacol , vol.17 , pp. 441-446
    • Mihaly, G.W.1    Ward, S.A.2    Edwards, G.3    Orme, L.E.M.4    Breckenridge, A.M.5
  • 13
    • 0020287584 scopus 로고
    • Highperformance liquid chromatographic analysis of the metabolism of primaquine and the identification of a new mammalian metabolite
    • Baker, J.K.; McChesney, J.D.; Hufford, C.D.; Clarck, A.M. Highperformance liquid chromatographic analysis of the metabolism of primaquine and the identification of a new mammalian metabolite. J. Chromatogr. 1982, 230, 69-77.
    • (1982) J. Chromatogr , vol.230 , pp. 69-77
    • Baker, J.K.1    McChesney, J.D.2    Hufford, C.D.3    Clarck, A.M.4
  • 15
    • 0021181651 scopus 로고
    • Highperformance liquid chromatographic ultraviolet determination of primaquine and its metabolites in human plasma and urine
    • Parkhurst, G.W.; Nora, M.V.; Thomas, R.W.; Carson, P.E. Highperformance liquid chromatographic ultraviolet determination of primaquine and its metabolites in human plasma and urine. J. Pharm. Sci., 1984, 73, 1329-1331.
    • (1984) J. Pharm. Sci , vol.73 , pp. 1329-1331
    • Parkhurst, G.W.1    Nora, M.V.2    Thomas, R.W.3    Carson, P.E.4
  • 16
    • 0021229470 scopus 로고
    • Pharmacokinetics of primaquine: Identification of the carboxylic acid derivative as a major plasma metabolite
    • Mihaly, G.W.; Ward, S.A.; Edwards, G.; Breckenridge, A.M. Pharmacokinetics of primaquine: identification of the carboxylic acid derivative as a major plasma metabolite. Br. J. Clin. Pharmacol., 1984, 17, 441-446.
    • (1984) Br. J. Clin. Pharmacol , vol.17 , pp. 441-446
    • Mihaly, G.W.1    Ward, S.A.2    Edwards, G.3    Breckenridge, A.M.4
  • 17
    • 0021176348 scopus 로고
    • Highperformance liquid chromatographic-electrochemical assay method for primaquine in plasma and urine
    • Nora, M.V.; Parkhurst, G.W.; Thomas, R.W.; Carson, P.E. Highperformance liquid chromatographic-electrochemical assay method for primaquine in plasma and urine. J. Chromatogr., 1984, 307, 451-456.
    • (1984) J. Chromatogr , vol.307 , pp. 451-456
    • Nora, M.V.1    Parkhurst, G.W.2    Thomas, R.W.3    Carson, P.E.4
  • 18
    • 0022005525 scopus 로고
    • Excretion of metabolites in bile following the administration of primaquine to rats
    • Baker, J.K.; McChesney, J.D.; Walker, L.A. Excretion of metabolites in bile following the administration of primaquine to rats. Pharm. Res., 1985, 2, 231-233.
    • (1985) Pharm. Res , vol.2 , pp. 231-233
    • Baker, J.K.1    McChesney, J.D.2    Walker, L.A.3
  • 19
    • 0025916444 scopus 로고
    • The conversion of primaquine into primaquine-aldehyde, primaquinealcohol, and carboxyprimaquine, a major plasma metabolite
    • Frischer, H.; Mellovity, R.L.; Ahmad, T.; Nora, M.V. The conversion of primaquine into primaquine-aldehyde, primaquinealcohol, and carboxyprimaquine, a major plasma metabolite. J. Lab. Clin. Med., 1991, 117, 468-476.
    • (1991) J. Lab. Clin. Med , vol.117 , pp. 468-476
    • Frischer, H.1    Mellovity, R.L.2    Ahmad, T.3    Nora, M.V.4
  • 21
    • 0021336555 scopus 로고
    • In vitro metabolism of the antimalarial agent primaquine by mouse liver enzymes and identification of a methemoglobin-forming metabolite
    • Strother, A.; Allahyari, R.; Buchholz, J.; Fraser, I.M.; Tilton, B.E. In vitro metabolism of the antimalarial agent primaquine by mouse liver enzymes and identification of a methemoglobin-forming metabolite. Drug Metab. Dispos. 1984, 12, 35-44.
    • (1984) Drug Metab. Dispos , vol.12 , pp. 35-44
    • Strother, A.1    Allahyari, R.2    Buchholz, J.3    Fraser, I.M.4    Tilton, B.E.5
  • 22
    • 0023924545 scopus 로고
    • Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine
    • Fletcher, K.A.; Barton, P.F.; Kelly, J.A. Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine. Biochem. Pharmacol. 1988, 37, 2683-2690.
    • (1988) Biochem. Pharmacol , vol.37 , pp. 2683-2690
    • Fletcher, K.A.1    Barton, P.F.2    Kelly, J.A.3
  • 23
    • 0022342389 scopus 로고
    • Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolyzates
    • Link, C.M.; Theoharides, A.D.; Anders, J.C.; Chung, H.; Canfield, C.J. Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolyzates. Toxicol. Appl. Pharmacol., 1985, 81,192-202.
    • (1985) Toxicol. Appl. Pharmacol , vol.81 , pp. 192-202
    • Link, C.M.1    Theoharides, A.D.2    Anders, J.C.3    Chung, H.4    Canfield, C.J.5
  • 24
    • 0021320710 scopus 로고
    • Synthesis of certain hydroxy analogs of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes
    • Allahyari, R.; Strother, A.; Fraser, I.M.; Verbiscar, A.J. Synthesis of certain hydroxy analogs of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes. J. Med. Chem., 1984, 27, 407-410.
    • (1984) J. Med. Chem , vol.27 , pp. 407-410
    • Allahyari, R.1    Strother, A.2    Fraser, I.M.3    Verbiscar, A.J.4
  • 25
    • 0022453810 scopus 로고
    • Oxidative activity of hydroxylated primaquine analogs. Non-toxicity to glucose-6-phosphate dehydrogenase-deficient human red blood cells in vitro
    • Baird, J.K.; Davidson, D.E., Jr.; Decker-Jackson, J.E. Oxidative activity of hydroxylated primaquine analogs. Non-toxicity to glucose-6-phosphate dehydrogenase-deficient human red blood cells in vitro. Biochem. Pharmacol., 1986, 1, 1091-1098.
    • (1986) Biochem. Pharmacol , vol.1 , pp. 1091-1098
    • Baird, J.K.1    Davidson Jr., D.E.2    Decker-Jackson, J.E.3
  • 26
    • 0025962234 scopus 로고
    • Susceptibility of glucose-6-phosphate dehydrogenase deficient red cells to primaquine, primaquine enantiomers, and its two putative metabolites. II. Effect on red blood cell membrane, lipid peroxidation, MC-540 staining, and scanning electron microscopic studies
    • Agarwal, S.; Gupta, U.R.; Daniel, C.S.; Gupta, R.C.; Anand, N.; Agarwal, S.S., Susceptibility of glucose-6-phosphate dehydrogenase deficient red cells to primaquine, primaquine enantiomers, and its two putative metabolites. II. Effect on red blood cell membrane, lipid peroxidation, MC-540 staining, and scanning electron microscopic studies. Biochem Pharmacol., 1991, 41, 17-21.
    • (1991) Biochem Pharmacol , vol.41 , pp. 17-21
    • Agarwal, S.1    Gupta, U.R.2    Daniel, C.S.3    Gupta, R.C.4    Anand, N.5    Agarwal, S.S.6
  • 27
    • 0026630568 scopus 로고
    • Hydroxylated metabolites of the antimalarial drug primaquine
    • Vásquez-Vivar, J.; Augusto, O. Hydroxylated metabolites of the antimalarial drug primaquine. J. Biol. Chem., 1992, 267, 6848-6854.
    • (1992) J. Biol. Chem , vol.267 , pp. 6848-6854
    • Vásquez-Vivar, J.1    Augusto, O.2
  • 28
    • 84987425635 scopus 로고
    • The identification of 6-methoxy 8-aminoquinoline as a metabolite of primaquine in man
    • Baty, J.D.; Price-Evans, D.A.; Robinson, P.A. The identification of 6-methoxy 8-aminoquinoline as a metabolite of primaquine in man. Biomed. Mass Spectrom., 1975, 2, 304-306.
    • (1975) Biomed. Mass Spectrom , vol.2 , pp. 304-306
    • Baty, J.D.1    Price-Evans, D.A.2    Robinson, P.A.3
  • 29
    • 0035028874 scopus 로고    scopus 로고
    • Primaquine-induced hemolytic anemia: Formation and hemotoxicity of the arylhydroxylamine metabolite 6-methoxy-8-hydroxylaminoquinoline
    • Bolchoz, L.J.C.; Budinsky, R.A.; McMillan, D.C.; Jollow, D.J. Primaquine-induced hemolytic anemia: formation and hemotoxicity of the arylhydroxylamine metabolite 6-methoxy-8-hydroxylaminoquinoline. J. Pharmacol. Exp. Ther., 2001, 297, 509-515.
    • (2001) J. Pharmacol. Exp. Ther , vol.297 , pp. 509-515
    • Bolchoz, L.J.C.1    Budinsky, R.A.2    McMillan, D.C.3    Jollow, D.J.4
  • 31
    • 54549090856 scopus 로고    scopus 로고
    • 1-acylation of imidazolidin-4-one derivatives of the antimalarial drug primaquine
    • 1-acylation of imidazolidin-4-one derivatives of the antimalarial drug primaquine. Tetrahedron, 2008, 64, 11144-11149.
    • (2008) Tetrahedron , vol.64 , pp. 11144-11149
    • Vale, N.1    Matos, J.2    Moreira, R.3    Gomes, P.4
  • 33
    • 71849088617 scopus 로고    scopus 로고
    • Anti-tumoral activity of imidazoquines, a new class of antimalarials derived from primaquine
    • Fernandes, I.; Vale, N.; de Freitas, V.; Moreira, R.; Mateus, N.; Gomes, P. Anti-tumoral activity of imidazoquines, a new class of antimalarials derived from primaquine. Bioorg. Med. Chem. Lett., 2009, 19, 6914-6917.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 6914-6917
    • Fernandes, I.1    Vale, N.2    de Freitas, V.3    Moreira, R.4    Mateus, N.5    Gomes, P.6
  • 34
    • 0038278508 scopus 로고    scopus 로고
    • An update on in vitro test methods in human hepatic drug biotransformation research: Pros and cons
    • Brandon, E.F.; Raap, C.D.; Meijerman, I.; Beijnen, J.H.; Schellens, J.H. An update on in vitro test methods in human hepatic drug biotransformation research: pros and cons. Toxicol. Appl. Pharmacol., 2003, 189, 233-246.
    • (2003) Toxicol. Appl. Pharmacol , vol.189 , pp. 233-246
    • Brandon, E.F.1    Raap, C.D.2    Meijerman, I.3    Beijnen, J.H.4    Schellens, J.H.5
  • 35
    • 0031735953 scopus 로고    scopus 로고
    • Sex-and strain-specific expression of cytochrome P450s in ochratoxin A-induced genotoxicity and carcinogenicity in rats
    • Pfohl-Leszkowicz, A.; Pinelli, E.; Bartsch, H.; Mohr, U.; Castegnaro, M., Sex-and strain-specific expression of cytochrome P450s in ochratoxin A-induced genotoxicity and carcinogenicity in rats. Mol. Carcinog., 1998, 23, 76-85.
    • (1998) Mol. Carcinog , vol.23 , pp. 76-85
    • Pfohl-Leszkowicz, A.1    Pinelli, E.2    Bartsch, H.3    Mohr, U.4    Castegnaro, M.5
  • 36
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding
    • Bradford, M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding. Anal. Biochem., 1976, 72, 248-54.
    • (1976) Anal. Biochem , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 38
    • 36949024918 scopus 로고    scopus 로고
    • The conduct of drug metabolism studies considered good practice (II): In vitro experiments
    • Jia, L.; X. Liu. The conduct of drug metabolism studies considered good practice (II): in vitro experiments. Curr. Drug Metabol., 2007, 8, 822-829.
    • (2007) Curr. Drug Metabol , vol.8 , pp. 822-829
    • Jia, L.1    Liu, X.2
  • 39
    • 0016829492 scopus 로고
    • Catechol-O-methyl transferase: Pharmacological aspects and physiological role
    • Guldberg, H.C.; Marsden, C.A., Catechol-O-methyl transferase: pharmacological aspects and physiological role. Pharmacol. Rev., 1975, 27, 135-206.
    • (1975) Pharmacol. Rev , vol.27 , pp. 135-206
    • Guldberg, H.C.1    Marsden, C.A.2
  • 40
    • 0025978802 scopus 로고
    • Purification and partial sequence analysis of the soluble catechol-O-methyltransferase from human placenta: Comparison to the rat liver enzyme
    • Tilgmann, C.; Kalkkinen, N., Purification and partial sequence analysis of the soluble catechol-O-methyltransferase from human placenta: Comparison to the rat liver enzyme. Biochem. Biophys. Res. Commun., 1991, 174, 995-1002.
    • (1991) Biochem. Biophys. Res. Commun , vol.174 , pp. 995-1002
    • Tilgmann, C.1    Kalkkinen, N.2
  • 43
    • 0026486256 scopus 로고
    • Characteristics of catechol O-methyltransferase (COMT) and properties of selective COMT inhibitors
    • Maennistoe, P. T.; Ulmanen, I.; Lundstroem, K.; Taskinen, J. Characteristics of catechol O-methyltransferase (COMT) and properties of selective COMT inhibitors. Prog. Drug Res., 1992, 39, 291.
    • (1992) Prog. Drug Res , vol.39 , pp. 291
    • Maennistoe, P.T.1    Ulmanen, I.2    Lundstroem, K.3    Taskinen, J.4
  • 44
    • 0025284207 scopus 로고
    • UDP-glucuronosyltransferases: A family of detoxifying enzymes
    • Tephly, T. R.; Burchell, B. UDP-glucuronosyltransferases: a family of detoxifying enzymes. Trends Pharmacol. Sci., 1990, 11, 276-279.
    • (1990) Trends Pharmacol. Sci , vol.11 , pp. 276-279
    • Tephly, T.R.1    Burchell, B.2
  • 47
    • 0022969280 scopus 로고
    • Characterization of the urine metabolites of primaquine in rats
    • Baker, J.K.; McChesney, J.D.; Jorge, L.F. Characterization of the urine metabolites of primaquine in rats. Pharm. Res. 1986, 3, 132-141.
    • (1986) Pharm. Res , vol.3 , pp. 132-141
    • Baker, J.K.1    McChesney, J.D.2    Jorge, L.F.3
  • 48
    • 11144271522 scopus 로고    scopus 로고
    • Characterization of afloqualone Nglucuronidation: Species differences and identification of human UDP-glucuronosyltransferase isoform(s)
    • Kaji, H.; Kume, T. Characterization of afloqualone Nglucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s). Drug Metabol. Dispos., 2005, 33, 60-67.
    • (2005) Drug Metabol. Dispos , vol.33 , pp. 60-67
    • Kaji, H.1    Kume, T.2
  • 49
    • 0032869568 scopus 로고    scopus 로고
    • Glucuronidation of benzidine and its metabolites by cDNA-expressed human UDP-glucuronosyltransferases and pH stability of glucoronides
    • Ciotti, M.; Lakshmi, V.M.; Basu, N.; Davis, B.B.; Owens, I.S.; Zenser, T.V.; Glucuronidation of benzidine and its metabolites by cDNA-expressed human UDP-glucuronosyltransferases and pH stability of glucoronides. Carcinogenesis, 1999, 20, 1963-1969.
    • (1999) Carcinogenesis , vol.20 , pp. 1963-1969
    • Ciotti, M.1    Lakshmi, V.M.2    Basu, N.3    Davis, B.B.4    Owens, I.S.5    Zenser, T.V.6
  • 50
    • 1242294484 scopus 로고    scopus 로고
    • A major fraction of endoplasmic reticulum-located glutathione is present as mixed disulfides with protein
    • Bass, R.; Ruddock, L. W.; Klappa, P.; Freedman, R. B. A major fraction of endoplasmic reticulum-located glutathione is present as mixed disulfides with protein. J. Biol. Chem., 2004, 279, 5257-5262.
    • (2004) J. Biol. Chem , vol.279 , pp. 5257-5262
    • Bass, R.1    Ruddock, L.W.2    Klappa, P.3    Freedman, R.B.4
  • 51
    • 0032864017 scopus 로고    scopus 로고
    • Glutathione conjugation of electrophilic metabolites of 1-nitronaphthalene in rat tracheobronchial airways and liver: Identification by mass spectrometry and proton nuclear magnetic resonance spectrometry
    • Watt, K.C.; Morin, D.M.; Kurth, M.J.; Mercer, R.S.; Plopper, C.G.; Buckpitt, A.R. Glutathione conjugation of electrophilic metabolites of 1-nitronaphthalene in rat tracheobronchial airways and liver: identification by mass spectrometry and proton nuclear magnetic resonance spectrometry. Chem. Res. Toxicol., 1999, 12, 831-839.
    • (1999) Chem. Res. Toxicol , vol.12 , pp. 831-839
    • Watt, K.C.1    Morin, D.M.2    Kurth, M.J.3    Mercer, R.S.4    Plopper, C.G.5    Buckpitt, A.R.6
  • 52
    • 78650521002 scopus 로고    scopus 로고
    • Evidence of the formation of direct covalent adducts of primaquine, 2-tert-butylprimaquine (NP-96) and monohydroxy metabolite of NP-96 with glutathione and N-acetylcysteine
    • Garg, A.; Prasad, B.; Takwani, H.; Jain, M.; Jain, R.; Singh, S. Evidence of the formation of direct covalent adducts of primaquine, 2-tert-butylprimaquine (NP-96) and monohydroxy metabolite of NP-96 with glutathione and N-acetylcysteine. J. Chrom. B, 2011, 879, 1-7.
    • (2011) J. Chrom. B , vol.879 , pp. 1-7
    • Garg, A.1    Prasad, B.2    Takwani, H.3    Jain, M.4    Jain, R.5    Singh, S.6
  • 54
    • 53149103554 scopus 로고    scopus 로고
    • Electrospray ionization-ion trap mass spectrometry study of PQAAPro and PQProAA mimetic derivatives of the antimalarial primaquine
    • Vale, N.; Matos, J.; Moreira, R.; Gomes, P. Electrospray ionization-ion trap mass spectrometry study of PQAAPro and PQProAA mimetic derivatives of the antimalarial primaquine. J. Am. Soc. Mass Spectrom. 2008, 19, 1476-1490.
    • (2008) J. Am. Soc. Mass Spectrom , vol.19 , pp. 1476-1490
    • Vale, N.1    Matos, J.2    Moreira, R.3    Gomes, P.4
  • 55
    • 64249118390 scopus 로고    scopus 로고
    • Primaquine dipeptide derivatives bearing an imidazolidin-4-one moiety at the N-terminus as potential antimalarial prodrugs
    • Vale, N.; Nogueira, F.; do Rosário, V.; Gomes, P.; Moreira, R. Primaquine dipeptide derivatives bearing an imidazolidin-4-one moiety at the N-terminus as potential antimalarial prodrugs. Eur. J. Med. Chem. 2009, 44, 2506-2516.
    • (2009) Eur. J. Med. Chem , vol.44 , pp. 2506-2516
    • Vale, N.1    Nogueira, F.2    do Rosário, V.3    Gomes, P.4    Moreira, R.5
  • 56
    • 34247266100 scopus 로고    scopus 로고
    • Plasmodium vivax in Africa: Hidden in plain sight?
    • Rosenberg, R. Plasmodium vivax in Africa: hidden in plain sight? Trends Parasitol. 2007, 23, 193-196.
    • (2007) Trends Parasitol , vol.23 , pp. 193-196
    • Rosenberg, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.