메뉴 건너뛰기




Volumn 51, Issue 8, 2007, Pages 2842-2847

2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization

Author keywords

[No Author keywords available]

Indexed keywords

2 TERT BUTYL 8 QUINOLINAMINE DERIVATIVE; HEMOZOIN; PRIMAQUINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34547626993     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.00288-07     Document Type: Article
Times cited : (23)

References (42)
  • 1
    • 0029953812 scopus 로고    scopus 로고
    • The iron environment in heme and heme-antimalarial complexes of pharmacological interest
    • Adams, P. A., P. A. Herman, T. J. Egan, P. J. Marsh, and J. Silver. 1996. The iron environment in heme and heme-antimalarial complexes of pharmacological interest. J. Inorg. Biochem. 63:69-77.
    • (1996) J. Inorg. Biochem , vol.63 , pp. 69-77
    • Adams, P.A.1    Herman, P.A.2    Egan, T.J.3    Marsh, P.J.4    Silver, J.5
  • 4
    • 0028828562 scopus 로고
    • Heme degradation in the presence of glutathione. A proposed mechanism to account for the high levels of non-heme iron found in the membranes of hemoglobinopathic red blood cells
    • Atamna, H., and H. Ginsburg. 1995. Heme degradation in the presence of glutathione. A proposed mechanism to account for the high levels of non-heme iron found in the membranes of hemoglobinopathic red blood cells. J. Biol. Chem. 270:24876-24883.
    • (1995) J. Biol. Chem , vol.270 , pp. 24876-24883
    • Atamna, H.1    Ginsburg, H.2
  • 6
    • 0036478819 scopus 로고    scopus 로고
    • Alcohol-water as a novel medium for beta-hematin preparation
    • Blauer, G., and M. Akkawi. 2002. Alcohol-water as a novel medium for beta-hematin preparation. Arch. Biochem. Biophys. 398:7-11.
    • (2002) Arch. Biochem. Biophys , vol.398 , pp. 7-11
    • Blauer, G.1    Akkawi, M.2
  • 7
    • 0031021734 scopus 로고    scopus 로고
    • Characterization of the products of the heme detoxification pathway in malarial late trophozoites by X-ray diffraction
    • Bohle, D. S., R. E. Dinnebier, S. K. Madsen, and P. W. Stephens. 1997. Characterization of the products of the heme detoxification pathway in malarial late trophozoites by X-ray diffraction. J. Biol. Chem. 272:713-716.
    • (1997) J. Biol. Chem , vol.272 , pp. 713-716
    • Bohle, D.S.1    Dinnebier, R.E.2    Madsen, S.K.3    Stephens, P.W.4
  • 8
    • 0033973854 scopus 로고    scopus 로고
    • Malaria: New ideas, old problems, new technologies
    • Butcher, G. A., R. E. Sinden, and C. Curtis. 2000. Malaria: new ideas, old problems, new technologies. Parasitol. Today 16:43-44.
    • (2000) Parasitol. Today , vol.16 , pp. 43-44
    • Butcher, G.A.1    Sinden, R.E.2    Curtis, C.3
  • 9
    • 0028947372 scopus 로고
    • Malarial haemozoin/beta-haematin supports haem polymerization in the absence of protein
    • Dorn, A., R. Stoffel, H. Matile, A. Bubendorf, and R. G. Ridley. 1995. Malarial haemozoin/beta-haematin supports haem polymerization in the absence of protein. Nature 374:269-271.
    • (1995) Nature , vol.374 , pp. 269-271
    • Dorn, A.1    Stoffel, R.2    Matile, H.3    Bubendorf, A.4    Ridley, R.G.5
  • 10
    • 0032520664 scopus 로고    scopus 로고
    • An assessment of drug-haematin binding as a mechanism for inhibition of haematin polymerisation by quinoline antimalarials
    • Dorn, A., S. R. Vippagunta, H. Matile, C. Jaquet, J. L. Vennerstrom, and R. G. Ridley. 1998. An assessment of drug-haematin binding as a mechanism for inhibition of haematin polymerisation by quinoline antimalarials. Biochem. Pharmacol. 55:727-736.
    • (1998) Biochem. Pharmacol , vol.55 , pp. 727-736
    • Dorn, A.1    Vippagunta, S.R.2    Matile, H.3    Jaquet, C.4    Vennerstrom, J.L.5    Ridley, R.G.6
  • 13
    • 0032919280 scopus 로고    scopus 로고
    • Characterisation of synthetic beta-haematin and effects of the antimalarial drugs quinidine, halofantrine, desbutylhalofantrine and mefloquine on its formation
    • Egan, T. J., E. Hempelmann, and W. W. Mavuso. 1999. Characterisation of synthetic beta-haematin and effects of the antimalarial drugs quinidine, halofantrine, desbutylhalofantrine and mefloquine on its formation. J. Inorg. Biochem. 73:101-107.
    • (1999) J. Inorg. Biochem , vol.73 , pp. 101-107
    • Egan, T.J.1    Hempelmann, E.2    Mavuso, W.W.3
  • 14
    • 0034719487 scopus 로고    scopus 로고
    • Structure-function relationships in aminoquinolines: Effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of beta-hematin formation, and antiplasmodial activity
    • Egan, T. J., R. Hunter, C. H. Kaschula, H. M. Marques, A. Misplon, and J. Walden. 2000. Structure-function relationships in aminoquinolines: effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of beta-hematin formation, and antiplasmodial activity. J. Med. Chem. 43:283-291.
    • (2000) J. Med. Chem , vol.43 , pp. 283-291
    • Egan, T.J.1    Hunter, R.2    Kaschula, C.H.3    Marques, H.M.4    Misplon, A.5    Walden, J.6
  • 15
    • 0030870923 scopus 로고    scopus 로고
    • Thermo dynamic factors controlling the interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX
    • Egan, T. J., W. W. Mavuso, D. C. Ross, and H. M. Marques. 1997. Thermo dynamic factors controlling the interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX. J. Inorg. Biochem. 68:137-145.
    • (1997) J. Inorg. Biochem , vol.68 , pp. 137-145
    • Egan, T.J.1    Mavuso, W.W.2    Ross, D.C.3    Marques, H.M.4
  • 16
    • 1142297431 scopus 로고    scopus 로고
    • Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs
    • Fitch, C. D. 2004. Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 74:1957-1972.
    • (2004) Life Sci , vol.74 , pp. 1957-1972
    • Fitch, C.D.1
  • 17
    • 0030879653 scopus 로고    scopus 로고
    • Hemoglobin metabolism in the malaria parasite Plasmodium falciparum
    • Francis, S. E., D. J. Sullivan, Jr., and D. E. Goldberg. 1997. Hemoglobin metabolism in the malaria parasite Plasmodium falciparum. Annu. Rev. Microbiol. 51:97-123.
    • (1997) Annu. Rev. Microbiol , vol.51 , pp. 97-123
    • Francis, S.E.1    Sullivan Jr., D.J.2    Goldberg, D.E.3
  • 18
    • 0020578902 scopus 로고
    • The effect of ferriprotoporphyrin IX and chloroquine on phospholipid monolayers and the possible implications to antimalarial activity
    • Ginsburg, H., and R. A. Demel. 1983. The effect of ferriprotoporphyrin IX and chloroquine on phospholipid monolayers and the possible implications to antimalarial activity. Biochim. Biophys. Acta 732:316-319.
    • (1983) Biochim. Biophys. Acta , vol.732 , pp. 316-319
    • Ginsburg, H.1    Demel, R.A.2
  • 20
    • 0037040221 scopus 로고    scopus 로고
    • Clotrimazole binds to heme and enhances hemedependent hemolysis: Proposed antimalarial mechanism of clotrimazole
    • Huy, N. T., K. Kamei, T. Yamamoto, Y. Kondo, K. Kanaori, R. Takano, K. Tajima, and S. Hara. 2002. Clotrimazole binds to heme and enhances hemedependent hemolysis: proposed antimalarial mechanism of clotrimazole. J. Biol. Chem. 277:4152-4158.
    • (2002) J. Biol. Chem , vol.277 , pp. 4152-4158
    • Huy, N.T.1    Kamei, K.2    Yamamoto, T.3    Kondo, Y.4    Kanaori, K.5    Takano, R.6    Tajima, K.7    Hara, S.8
  • 21
    • 33847641516 scopus 로고    scopus 로고
    • Alcohols induce beta-hematin formation via the dissociation of aggregated heme and reduction in interfacial tension of the solution
    • Huy, N. T., A. Maeda, D. T. Uyen, D. T. Trang, M. Sasai, T. Shiono, T. Oida, S. Harada, and K. Kamei. 2007. Alcohols induce beta-hematin formation via the dissociation of aggregated heme and reduction in interfacial tension of the solution. Acta Trop. 101:130-138.
    • (2007) Acta Trop , vol.101 , pp. 130-138
    • Huy, N.T.1    Maeda, A.2    Uyen, D.T.3    Trang, D.T.4    Sasai, M.5    Shiono, T.6    Oida, T.7    Harada, S.8    Kamei, K.9
  • 23
    • 12744256288 scopus 로고    scopus 로고
    • Enhancement of heme-induced membrane damage by the anti-malarial clotrimazole: The role of colloid-osmotic forces
    • Huy, N. T., R. Takano, S. Hara, and K. Kamei. 2004. Enhancement of heme-induced membrane damage by the anti-malarial clotrimazole: the role of colloid-osmotic forces. Biol. Pharm. Bull. 27:361-365.
    • (2004) Biol. Pharm. Bull , vol.27 , pp. 361-365
    • Huy, N.T.1    Takano, R.2    Hara, S.3    Kamei, K.4
  • 24
    • 33845983685 scopus 로고    scopus 로고
    • Simple colorimetric inhibition assay of heme crystallization for high-throughput screening of antimalarial compounds
    • Huy, N. T., D. T. Uyen, A. Maeda, D. T. Trang, T. Oida, S. Harada, and K. Kamei. 2007. Simple colorimetric inhibition assay of heme crystallization for high-throughput screening of antimalarial compounds. Antimicrob. Agents Chemother. 51:350-353.
    • (2007) Antimicrob. Agents Chemother , vol.51 , pp. 350-353
    • Huy, N.T.1    Uyen, D.T.2    Maeda, A.3    Trang, D.T.4    Oida, T.5    Harada, S.6    Kamei, K.7
  • 25
    • 33745214879 scopus 로고    scopus 로고
    • A simple and rapid colorimetric method to measure hemozoin crystal growth in vitro
    • Huy, N. T., D. T. Uyen, M. Sasai, D. T. Trang, T. Shiono, S. Harada, and K. Kamei. 2006. A simple and rapid colorimetric method to measure hemozoin crystal growth in vitro. Anal. Biochem. 354:305-307.
    • (2006) Anal. Biochem , vol.354 , pp. 305-307
    • Huy, N.T.1    Uyen, D.T.2    Sasai, M.3    Trang, D.T.4    Shiono, T.5    Harada, S.6    Kamei, K.7
  • 26
    • 1342279560 scopus 로고    scopus 로고
    • Synthesis and blood-schizontocidal antimalarial activities of 2-substituted/2,5- disubstituted-8-quinolinamines and some of their amino acid conjugates
    • Jain, M., S. Vangapandu, S. Sachdeva, and R. Jain. 2004. Synthesis and blood-schizontocidal antimalarial activities of 2-substituted/2,5- disubstituted-8-quinolinamines and some of their amino acid conjugates. Bioorg. Med. Chem. 12:1003-1010.
    • (2004) Bioorg. Med. Chem , vol.12 , pp. 1003-1010
    • Jain, M.1    Vangapandu, S.2    Sachdeva, S.3    Jain, R.4
  • 27
    • 9144273190 scopus 로고    scopus 로고
    • Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity
    • Jain, M., S. Vangapandu, S. Sachdeva, S. Singh, P. P. Singh, G. B. Jena, K. Tikoo, P. Ramarao, C. L. Kaul, and R. Jain. 2004. Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity. J. Med. Chem. 47:285-287.
    • (2004) J. Med. Chem , vol.47 , pp. 285-287
    • Jain, M.1    Vangapandu, S.2    Sachdeva, S.3    Singh, S.4    Singh, P.P.5    Jena, G.B.6    Tikoo, K.7    Ramarao, P.8    Kaul, C.L.9    Jain, R.10
  • 29
    • 0020384171 scopus 로고
    • Antimalarials. 14. 5-(Aryloxy)-4-methylprimaquine analogues. A highly effective series of blood and tissue schizonticidal agents
    • LaMontagne, M. P., P. Blumbergs, and R. E. Strube. 1982. Antimalarials. 14. 5-(Aryloxy)-4-methylprimaquine analogues. A highly effective series of blood and tissue schizonticidal agents. J. Med. Chem. 25:1094-1097.
    • (1982) J. Med. Chem , vol.25 , pp. 1094-1097
    • LaMontagne, M.P.1    Blumbergs, P.2    Strube, R.E.3
  • 31
    • 16244365509 scopus 로고    scopus 로고
    • Destabilisation and subsequent lysis of human erythrocytes induced by Plasmodium falciparum haem products
    • Omodeo-Sale, F., A. Motti, A. Dondorp, N. J. White, and D. Taramelli. 2005. Destabilisation and subsequent lysis of human erythrocytes induced by Plasmodium falciparum haem products. Eur. J. Haematol. 74:324-332.
    • (2005) Eur. J. Haematol , vol.74 , pp. 324-332
    • Omodeo-Sale, F.1    Motti, A.2    Dondorp, A.3    White, N.J.4    Taramelli, D.5
  • 36
    • 0037021386 scopus 로고    scopus 로고
    • Theories on malarial pigment formation and quinoline action
    • Sullivan, D. J. 2002. Theories on malarial pigment formation and quinoline action. Int. J. Parasitol. 32:1645-1653.
    • (2002) Int. J. Parasitol , vol.32 , pp. 1645-1653
    • Sullivan, D.J.1
  • 37
    • 0030045312 scopus 로고    scopus 로고
    • Plasmodium hemozoin formation mediated by histidine-rich proteins
    • Sullivan, D. J., Jr., I. Y. Gluzman, and D. E. Goldberg. 1996. Plasmodium hemozoin formation mediated by histidine-rich proteins. Science 271:219-222.
    • (1996) Science , vol.271 , pp. 219-222
    • Sullivan Jr., D.J.1    Gluzman, I.Y.2    Goldberg, D.E.3
  • 38
    • 33750512152 scopus 로고    scopus 로고
    • 8-Aminoquinolines: Future role as antiprotozoal drugs
    • Tekwani, B. L., and L. A. Walker. 2006. 8-Aminoquinolines: future role as antiprotozoal drugs. Curr. Opin. Infect. Dis. 19:623-631.
    • (2006) Curr. Opin. Infect. Dis , vol.19 , pp. 623-631
    • Tekwani, B.L.1    Walker, L.A.2
  • 39
    • 12744273601 scopus 로고    scopus 로고
    • Targeting the hemozoin synthesis pathway for new antimalarial drug discovery: Technologies for in vitro beta-hematin formation assay
    • Tekwani, B. L., and L. A. Walker. 2005. Targeting the hemozoin synthesis pathway for new antimalarial drug discovery: technologies for in vitro beta-hematin formation assay. Comb. Chem. High Throughput Screen. 8:63-79.
    • (2005) Comb. Chem. High Throughput Screen , vol.8 , pp. 63-79
    • Tekwani, B.L.1    Walker, L.A.2
  • 40
    • 31844457268 scopus 로고    scopus 로고
    • Inhibition assay of beta-hematin formation initiated by lecithin for screening new antimalarial drugs
    • Trang, D. T., N. T. Huy, D. T. Uyen, M. Sasai, T. Shiono, S. Harada, and K. Kamei. 2006. Inhibition assay of beta-hematin formation initiated by lecithin for screening new antimalarial drugs. Anal. Biochem. 349:292-296.
    • (2006) Anal. Biochem , vol.349 , pp. 292-296
    • Trang, D.T.1    Huy, N.T.2    Uyen, D.T.3    Sasai, M.4    Shiono, T.5    Harada, S.6    Kamei, K.7
  • 41
    • 0035955435 scopus 로고    scopus 로고
    • In vitro beta-hematin formation assays with plasma of mice infected with Plasmodium yoelii and other parasite preparations: Comparative inhibition with quinoline and endoperoxide antimalarials
    • Tripathi, A. K., A. Gupta, S. K. Garg, and B. L. Tekwani. 2001. In vitro beta-hematin formation assays with plasma of mice infected with Plasmodium yoelii and other parasite preparations: comparative inhibition with quinoline and endoperoxide antimalarials. Life Sci. 69:2725-2733.
    • (2001) Life Sci , vol.69 , pp. 2725-2733
    • Tripathi, A.K.1    Gupta, A.2    Garg, S.K.3    Tekwani, B.L.4
  • 42
    • 0242626690 scopus 로고    scopus 로고
    • Raman imaging of hemozoin within the food vacuole of Plasmodium falciparum trophozoites
    • Wood, B. R., S. J. Langford, B. M. Cooke, F. K. Glenister, J. Lim, and D. McNaughton. 2003. Raman imaging of hemozoin within the food vacuole of Plasmodium falciparum trophozoites. FEBS Lett. 554:247-252.
    • (2003) FEBS Lett , vol.554 , pp. 247-252
    • Wood, B.R.1    Langford, S.J.2    Cooke, B.M.3    Glenister, F.K.4    Lim, J.5    McNaughton, D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.