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Volumn 49, Issue 24, 2006, Pages 7227-7233

New orally active derivatives of artemisinin with high efficacy against multidrug-resistant malaria in mice

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEETHER; DIHYDROARTEMISININ DERIVATIVE;

EID: 33845366593     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060826x     Document Type: Article
Times cited : (46)

References (40)
  • 1
    • 33845349706 scopus 로고    scopus 로고
    • CDRI Communication No.: 6999
    • CDRI Communication No.: 6999.
  • 2
    • 0012006323 scopus 로고    scopus 로고
    • W. H. O.
    • W. H. O. Drug Inf. Bull. 1999, 13, 9.
    • (1999) Drug Inf. Bull. , vol.13 , pp. 9
  • 3
    • 0021948029 scopus 로고
    • Qinghaosu (artemisinin): An antimalarial drug from China
    • For reviews on artemisinin and its analogues, see: (a) Klayman, D. L. Qinghaosu (artemisinin): an antimalarial drug from China. Science 1985, 228, 1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 4
    • 0023110445 scopus 로고
    • The chemistry, pharmacology, and clinical applications of qinghaosu (artemisinin) and its derivatives
    • (b) Luo, X. D.; Shen, C. C. The chemistry, pharmacology, and clinical applications of qinghaosu (artemisinin) and its derivatives. Med. Res. Rev. 1987, 7, 29-52.
    • (1987) Med. Res. Rev. , vol.7 , pp. 29-52
    • Luo, X.D.1    Shen, C.C.2
  • 5
    • 0000484009 scopus 로고    scopus 로고
    • Antimalarial activity of artemisinin (qinghaosu) and related trioxanes
    • (c) Cumming, J. N.; Ploypradith, P.; Posner, G. H. Antimalarial activity of artemisinin (qinghaosu) and related trioxanes. Adv. Pharmacol. 1997, 37, 2253-297.
    • (1997) Adv. Pharmacol. , vol.37 , pp. 2253-2297
    • Cumming, J.N.1    Ploypradith, P.2    Posner, G.H.3
  • 6
    • 0033165891 scopus 로고    scopus 로고
    • Recent developments on the chemistry and biological activity of artemisinin and related antimalarials
    • (d) Bhattacharya, A. K.; Sharma, R. P. Recent developments on the chemistry and biological activity of artemisinin and related antimalarials. Heterocycles 1999, 51, 1681-1745.
    • (1999) Heterocycles , vol.51 , pp. 1681-1745
    • Bhattacharya, A.K.1    Sharma, R.P.2
  • 7
    • 0037021402 scopus 로고    scopus 로고
    • Antimalarial chemotherapeutic peroxides: Artemisinin, yingzhaosu A and related compounds
    • (e) Borstnik, K.; Paik, I.; Shapiro, T. A.; Posner, G. H. Antimalarial chemotherapeutic peroxides: artemisinin, yingzhaosu A and related compounds. Int. J. Parasitol. 2002, 32, 1661-1667.
    • (2002) Int. J. Parasitol. , vol.32 , pp. 1661-1667
    • Borstnik, K.1    Paik, I.2    Shapiro, T.A.3    Posner, G.H.4
  • 8
    • 1642442453 scopus 로고    scopus 로고
    • Development of artemisinin and its structurally simplified trioxane derivatives as antimalarial drugs
    • (f) Ploypradith, P. Development of artemisinin and its structurally simplified trioxane derivatives as antimalarial drugs. Acta Trop. 2004, 89, 329-342.
    • (2004) Acta Trop. , vol.89 , pp. 329-342
    • Ploypradith, P.1
  • 9
    • 2542640961 scopus 로고    scopus 로고
    • A Medicinal chemistry perspective on artemisinin and related endoperoxides
    • (g) O'Neill, P. M.; Posner, G. H. A Medicinal chemistry perspective on artemisinin and related endoperoxides. J. Med. Chem. 2004, 47, 2945-2964.
    • (2004) J. Med. Chem. , vol.47 , pp. 2945-2964
    • O'Neill, P.M.1    Posner, G.H.2
  • 10
    • 0003015954 scopus 로고    scopus 로고
    • Current status of the artemisinin derivatives in the treatment of malaria with focus on arteether
    • (a) Asthana, O. P.; Srivastava, J. S.; Valecha, N. Current status of the artemisinin derivatives in the treatment of malaria with focus on arteether. J. Paras. Dis. 1997, 211, 1-12.
    • (1997) J. Paras. Dis. , vol.211 , pp. 1-12
    • Asthana, O.P.1    Srivastava, J.S.2    Valecha, N.3
  • 12
    • 0029894037 scopus 로고    scopus 로고
    • Artemisinin and the Antimalarial Endoperoxides: From Herbal Remedy to Targeted Chemotherapy
    • Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Artemisinin and the Antimalarial Endoperoxides: From Herbal Remedy to Targeted Chemotherapy. Microbiol. Rev. 1996, 60, 301-315.
    • (1996) Microbiol. Rev. , vol.60 , pp. 301-315
    • Meshnick, S.R.1    Taylor, T.E.2    Kamchonwongpaisan, S.3
  • 13
    • 0037186497 scopus 로고    scopus 로고
    • Mechanism-Based Design of Parasite-Targeted Artemisinin Derivatives: Synthesis and Antimalarial Activity of New Diamine Containing Analogues
    • (a) Hindley, S.; Ward, S. A.; Storr, R. C.; Searle, N. L.; Bray, P. G.; Park, B. K.; Davies, J.; O'Neill, P. M. Mechanism-Based Design of Parasite-Targeted Artemisinin Derivatives: Synthesis and Antimalarial Activity of New Diamine Containing Analogues. J. Med. Chem. 2002, 45, 1052-1063.
    • (2002) J. Med. Chem. , vol.45 , pp. 1052-1063
    • Hindley, S.1    Ward, S.A.2    Storr, R.C.3    Searle, N.L.4    Bray, P.G.5    Park, B.K.6    Davies, J.7    O'Neill, P.M.8
  • 14
    • 0037068498 scopus 로고    scopus 로고
    • Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and in Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates
    • (b) Avery, M. A.; Alvim-Gaston, M.; Vroman, J. A.; Wu, B.; Ager, A.; Peters, W.; Robinson, B. L.; Charman, W. Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and in Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates. J. Med. Chem. 2002, 45, 4321-4335.
    • (2002) J. Med. Chem. , vol.45 , pp. 4321-4335
    • Avery, M.A.1    Alvim-Gaston, M.2    Vroman, J.A.3    Wu, B.4    Ager, A.5    Peters, W.6    Robinson, B.L.7    Charman, W.8
  • 15
    • 0037435053 scopus 로고    scopus 로고
    • Orally Active, Antimalarial, Anticancer, Artemisinin-Derived Trioxane Dimers with High Stability and Efficacy
    • (c) Posner, G. H.; Paik, I.-H.; Sur, S.; McRiner, A. J.; Borstnik, K.; Xie, S.; Shapiro, T. A. Orally Active, Antimalarial, Anticancer, Artemisinin-Derived Trioxane Dimers with High Stability and Efficacy. J. Med. Chem. 2003, 46, 1060-1065.
    • (2003) J. Med. Chem. , vol.46 , pp. 1060-1065
    • Posner, G.H.1    Paik, I.-H.2    Sur, S.3    McRiner, A.J.4    Borstnik, K.5    Xie, S.6    Shapiro, T.A.7
  • 17
    • 33646461526 scopus 로고    scopus 로고
    • Second Generation, Orally Active, Antimalarial, Artemisinin-Derived Trioxane Dimers with High Stability, Efficacy, and Anticancer Activity
    • (e) Paik, I.-H.; Xie, S.; Shapiro, T. A.; Labonte, T.; Narducci Sarjeant, A. A.; Baege, A. C.; Posner, G. H. Second Generation, Orally Active, Antimalarial, Artemisinin-Derived Trioxane Dimers with High Stability, Efficacy, and Anticancer Activity J. Med. Chem. 2006, 49(9), 2731-2734.
    • (2006) J. Med. Chem. , vol.49 , Issue.9 , pp. 2731-2734
    • Paik, I.-H.1    Xie, S.2    Shapiro, T.A.3    Labonte, T.4    Narducci Sarjeant, A.A.5    Baege, A.C.6    Posner, G.H.7
  • 18
    • 33845352781 scopus 로고    scopus 로고
    • Novel lipophilic ether derivatives of dihydroartemisinin as antimalarials
    • Indian Patent application. No. 0201 DEL 2004, Filing Date 14-02-2005
    • This work has been covered in a patent: Singh, C.; Chaudhary, S.; Puri, S. K. Novel lipophilic ether derivatives of dihydroartemisinin as antimalarials. Indian Patent application. No. 0201 DEL 2004, Filing Date 14-02-2005.
    • Singh, C.1    Chaudhary, S.2    Puri, S.K.3
  • 20
    • 0040263311 scopus 로고
    • Techniques for the study of drug response in experimental malaria
    • Academic Press: London
    • (a) Peters, W. Techniques for the study of drug response in experimental malaria. In Chemotherapy and drug resistance in malaria; Academic Press: London, 1970; pp 64-136.
    • (1970) Chemotherapy and Drug Resistance in Malaria , pp. 64-136
    • Peters, W.1
  • 21
    • 33845361504 scopus 로고    scopus 로고
    • note
    • 16 Mice treated with β-arteether served as positive control.
  • 22
    • 0028951562 scopus 로고
    • Antimalarial activity of new Dihydroartemisinin derivatives. 6. α-Alkylbenzylic Ethers
    • Lin, A. J.; Miller, R. E. Antimalarial activity of new Dihydroartemisinin derivatives. 6. α-Alkylbenzylic Ethers. J. Med. Chem. 1995, 38, 764-770.
    • (1995) J. Med. Chem. , vol.38 , pp. 764-770
    • Lin, A.J.1    Miller, R.E.2
  • 23
    • 4744374690 scopus 로고    scopus 로고
    • Synthesis of new 6-alkylvinyl/ arylalkylvinyl substituted 1, 2, 4-trioxanes active against multidrug-resistant malaria in mice
    • (a) Singh, C.; Gupta, N.; Puri, S. K. Synthesis of new 6-alkylvinyl/ arylalkylvinyl substituted 1, 2, 4-trioxanes active against multidrug-resistant malaria in mice. Bioorg. Med. Chem. 2004, 12, 5553-5562.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 5553-5562
    • Singh, C.1    Gupta, N.2    Puri, S.K.3
  • 24
    • 33845363105 scopus 로고    scopus 로고
    • Substituted 1,2,4-trioxanes useful as antimalarial agents and a process for the preparation thereof
    • US Patent 6737438 B2, dated May 18
    • (b) Singh, C.; Tiwari, P.; Puri, S. K. Substituted 1,2,4-trioxanes useful as antimalarial agents and a process for the preparation thereof. US Patent 6737438 B2, dated May 18, 2004.
    • (2004)
    • Singh, C.1    Tiwari, P.2    Puri, S.K.3
  • 25
    • 33845350595 scopus 로고    scopus 로고
    • Novel substituted 1, 2, 4-trioxanes as antimalarial agents
    • Indian Patent application. No. 1554 DEL 99, filing date Dec 12
    • (c) Singh, C.; Kanchan, R.; Puri, S. K. Novel substituted 1, 2, 4-trioxanes as antimalarial agents. Indian Patent application. No. 1554 DEL 99, filing date Dec 12, 1999.
    • (1999)
    • Singh, C.1    Kanchan, R.2    Puri, S.K.3
  • 26
    • 0000611178 scopus 로고
    • Drug Compendium
    • Mansch, C.; Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press.; Oxford, UK
    • (a) Craig, P. N. Drug Compendium. In Comprehensive Medicinal Chemistry, 1st ed.; Vol. 6. Mansch, C.; Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press.; Oxford, UK, 1990; pp 237-965.
    • (1990) Comprehensive Medicinal Chemistry, 1st Ed. , vol.6 , pp. 237-965
    • Craig, P.N.1
  • 32
    • 30444443786 scopus 로고    scopus 로고
    • Novel 4-Oxo-1, 4-dihydroquinoline-3-carboxamide Derivatives as New CB2 Cannabinoid Receptors Agonists: Synthesis, Pharmacological Properties and Molecular Modeling
    • (g) Stern, E.; Muccioli, G. G.; Millet, R.; Goossens, J.-F.; Farce, A.; Chavatte, P.; Poupaert, J. H.; Lambert, D. M.; Depreux, P.; Hénichart, J.-P. Novel 4-Oxo-1, 4-dihydroquinoline-3-carboxamide Derivatives as New CB2 Cannabinoid Receptors Agonists: Synthesis, Pharmacological Properties and Molecular Modeling. J. Med. Chem. 2006, 49(1), 70-79.
    • (2006) J. Med. Chem. , vol.49 , Issue.1 , pp. 70-79
    • Stern, E.1    Muccioli, G.G.2    Millet, R.3    Goossens, J.-F.4    Farce, A.5    Chavatte, P.6    Poupaert, J.H.7    Lambert, D.M.8    Depreux, P.9    Hénichart, J.-P.10
  • 33
    • 33646737506 scopus 로고    scopus 로고
    • Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G0-G1 Phase and Induces Differentiation in Leukemia Cells
    • (h) Roberti, M.; Pizzirani, D.; Recanatini M.; Simoni, D.; Grimaudo, S.; Cristina, A. D.; Abbadessa, V.; Gebbia, N.; Tolomeo, M.; Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G0-G1 Phase and Induces Differentiation in Leukemia Cells. J. Med. Chem. 2006, 49(10), 3012-3018.
    • (2006) J. Med. Chem. , vol.49 , Issue.10 , pp. 3012-3018
    • Roberti, M.1    Pizzirani, D.2    Recanatini, M.3    Simoni, D.4    Grimaudo, S.5    Cristina, A.D.6    Abbadessa, V.7    Gebbia, N.8    Tolomeo, M.9
  • 37
    • 0024360869 scopus 로고
    • Antimalarial Activity of New Water-Soluble Dihydroartemisinin Derivatives. 2. Stereospecificity of the Ether Side Chain
    • Compound 7 has been prepared earlier: Lin, A. J.; Lee, M.; Klayman, D. L. Antimalarial Activity of New Water-Soluble Dihydroartemisinin Derivatives. 2. Stereospecificity of the Ether Side Chain. J. Med. Chem. 1989, 32, 1249-1252.
    • (1989) J. Med. Chem. , vol.32 , pp. 1249-1252
    • Lin, A.J.1    Lee, M.2    Klayman, D.L.3
  • 38
    • 15444366107 scopus 로고    scopus 로고
    • Concentration and pH dependent aggregation of hydrophobic drug molecules and relevance to oral bioavailability
    • Frenkel, Y. V.; Clark, A. D., Jr.; Das, K.; Wang, Y.-H, Lewis, P. J.; Janssen, P. A. J.; Arnold, E. Concentration and pH dependent aggregation of hydrophobic drug molecules and relevance to oral bioavailability. J. Med. Chem. 2005, 48, 1974-1983.
    • (2005) J. Med. Chem. , vol.48 , pp. 1974-1983
    • Frenkel, Y.V.1    Clark Jr., A.D.2    Das, K.3    Wang, Y.-H.4    Lewis, P.J.5    Janssen, P.A.J.6    Arnold, E.7
  • 39
    • 33845350090 scopus 로고    scopus 로고
    • note
    • (a) 100% suppression of parasitemia means no parasites were detected in 50 oil immersion microscopic fields (parasites if at all present, are below the detection limit). The parasites present below the detection limit can multiply and eventually can be detected during observation on subsequent days. In such cases, though, the drug is providing near 100% suppression of the parasitaemia on day 4 but will not provide full protection to the treated mice in the 28 day survival assay. Multidrug-resistant Plasmodium yoelii nigeriensis used in this study is resistant to chloroquine, mefloquine, and halofantrine. (b) 100% protection means none of the treated mice developed patent infection during the 28 days observation period and hence were recorded as cured. Similarly, 20% protection means only one out of five mice was cured.
  • 40
    • 0033973112 scopus 로고    scopus 로고
    • Azithromycin: Antimalarial profile against blood- And sporozite-induced infections in mice and monkeys
    • Puri, S. K.; Singh, N. Azithromycin: antimalarial profile against blood- and sporozite-induced infections in mice and monkeys. Expl. Parasitol. 2000, 94, 8-14.
    • (2000) Expl. Parasitol. , vol.94 , pp. 8-14
    • Puri, S.K.1    Singh, N.2


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