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Volumn 53, Issue 8, 2010, Pages 3214-3226

Antimalarial versus cytotoxic properties of dual drugs derived from 4-aminoquinolines and mannich bases: Interaction with DNA

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; AMODIAQUINE; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; BETA HEMATIN; CHLOROQUINE; CYTOSINE; DEETHYLAMODIAQUINE; FERROQUINE; GUANINE; HEMATIN; HEME; IRON DERIVATIVE; MANNICH BASE; N [(7 CHLOROQUINOLIN 4 YL)ETHYL] N' (1 HEXAZIN 1 YL 3 PIPERIDIN 1 YLPROPYL)ETHANE 1,2 DIAMINE; N1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] N3,N3 DIMETHYL 1 PHENYLPROPANE 1,3 DIAMINE; PROTEIN INHIBITOR; QUININE; SR 97193; UNCLASSIFIED DRUG;

EID: 77951143202     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9018383     Document Type: Article
Times cited : (68)

References (52)
  • 2
    • 0035830368 scopus 로고    scopus 로고
    • The mechanism of beta-hematin formation in acetate solution. Parallels between hemozoin formation and biomineralization processes
    • Egan, T. J.; Mavuso, W. W.; Ncokazi, K. K. The mechanism of beta-hematin formation in acetate solution. Parallels between hemozoin formation and biomineralization processes Biochemistry 2001, 40, 204-213
    • (2001) Biochemistry , vol.40 , pp. 204-213
    • Egan, T.J.1    Mavuso, W.W.2    Ncokazi, K.K.3
  • 3
    • 0022548386 scopus 로고
    • Digestion of the host erythrocyte by malaria parasites is the primary target for quinoline-containing antimalarials
    • Zarchin, S; Krugliak, M; Ginsburg, H. Digestion of the host erythrocyte by malaria parasites is the primary target for quinoline-containing antimalarials Biochem. Pharmacol. 1986, 35, 2435-2442
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 2435-2442
    • Zarchin, S.1    Krugliak, M.2    Ginsburg, H.3
  • 5
    • 42049124049 scopus 로고    scopus 로고
    • Recent advances in understanding the mechanism of hemozoin (malaria pigment) formation
    • Egan, T. J. Recent advances in understanding the mechanism of hemozoin (malaria pigment) formation J. Inorg. Biochem. 2008, 102, 1288-1299
    • (2008) J. Inorg. Biochem. , vol.102 , pp. 1288-1299
    • Egan, T.J.1
  • 6
    • 0026863045 scopus 로고
    • Malaria pigment
    • Slater, A. F. G. Malaria Pigment Exp. Parasitol. 1992, 74, 362-365
    • (1992) Exp. Parasitol. , vol.74 , pp. 362-365
    • Slater, A.F.G.1
  • 7
    • 0042573722 scopus 로고    scopus 로고
    • Trans stimulation provides evidence for a drug efflux carrier as the mechanism of chloroquine resistance in Plasmodium falciparum
    • Sanchez, C. P.; Stein, W.; Lanzer, M. Trans stimulation provides evidence for a drug efflux carrier as the mechanism of chloroquine resistance in Plasmodium falciparum Biochemistry 2003, 42, 9383-9394
    • (2003) Biochemistry , vol.42 , pp. 9383-9394
    • Sanchez, C.P.1    Stein, W.2    Lanzer, M.3
  • 8
    • 11144279334 scopus 로고    scopus 로고
    • Evidence for a substrate specific and inhibitable drug efflux system in chloroquine resistant Plasmodium falciparum strains
    • Sanchez, C. P.; McLean, J. E.; Stein, W.; Lanzer, M. Evidence for a substrate specific and inhibitable drug efflux system in chloroquine resistant Plasmodium falciparum strains Biochemistry 2004, 43, 16365-16373
    • (2004) Biochemistry , vol.43 , pp. 16365-16373
    • Sanchez, C.P.1    McLean, J.E.2    Stein, W.3    Lanzer, M.4
  • 9
    • 22744436592 scopus 로고    scopus 로고
    • Evidence for a pfcrt-associated chloroquine efflux system in the human malarial parasite Plasmodium falciparum
    • Sanchez, C. P.; McLean, J. E.; Rohrbach, P.; Fidock, D. A.; Stein, W. D.; Lanzer, M. Evidence for a pfcrt-associated chloroquine efflux system in the human malarial parasite Plasmodium falciparum Biochemistry 2005, 44, 9862-9870
    • (2005) Biochemistry , vol.44 , pp. 9862-9870
    • Sanchez, C.P.1    McLean, J.E.2    Rohrbach, P.3    Fidock, D.A.4    Stein, W.D.5    Lanzer, M.6
  • 10
    • 34247364130 scopus 로고    scopus 로고
    • Differences in trans-stimulated chloroquine efflux kinetics are linked to PfCRT in Plasmodium falciparum
    • Sanchez, C. P.; Rohrbach, P.; McLean, J. E.; Fidock, D. A.; Stein, W. D.; Lanzer, M. Differences in trans-stimulated chloroquine efflux kinetics are linked to PfCRT in Plasmodium falciparum Mol. Microbiol. 2007, 64, 407-420
    • (2007) Mol. Microbiol. , vol.64 , pp. 407-420
    • Sanchez, C.P.1    Rohrbach, P.2    McLean, J.E.3    Fidock, D.A.4    Stein, W.D.5    Lanzer, M.6
  • 11
    • 0034655152 scopus 로고    scopus 로고
    • Deletion of the parasite-specific insertions and mutation of the catalytic triad in glutathione reductase from chloroquine-sensitive Plasmodium falciparum 3D7
    • Gilberger, T.-W.; Schirmer, R. H.; Walter, R. D.; Müller, S. Deletion of the parasite-specific insertions and mutation of the catalytic triad in glutathione reductase from chloroquine-sensitive Plasmodium falciparum 3D7 Mol. Biochem. Parasitol. 2000, 107, 169-179
    • (2000) Mol. Biochem. Parasitol. , vol.107 , pp. 169-179
    • Gilberger, T.-W.1    Schirmer, R.H.2    Walter, R.D.3    Müller, S.4
  • 12
    • 0037115759 scopus 로고    scopus 로고
    • Regulation of intracellular glutathione levels in erythrocytes infected with chloroquine-sensitive and chloroquine-resistant
    • Meierjohann, S.; Walter, R. D.; Müller, S. Regulation of intracellular glutathione levels in erythrocytes infected with chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum. Biochem J. 2002, 368, 761-768
    • (2002) Plasmodium Falciparum. Biochem J. , vol.368 , pp. 761-768
    • Meierjohann, S.1    Walter, R.D.2    Müller, S.3
  • 13
    • 71849091387 scopus 로고    scopus 로고
    • Antimalarial antimalarial activities of ferroquine conjugates with either glutathione reductase inhibitors or glutathione depletors via a hydrolyzable amide linker
    • Chavain, N.; Davioud-Charvet, E.; Trivelli, X.; Mbeki, L.; Rottmann, M.; Brun, R.; Biot, C. Antimalarial antimalarial activities of ferroquine conjugates with either glutathione reductase inhibitors or glutathione depletors via a hydrolyzable amide linker Bioorg. Med. Chem. 2009, 17, 8048-8059
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 8048-8059
    • Chavain, N.1    Davioud-Charvet, E.2    Trivelli, X.3    Mbeki, L.4    Rottmann, M.5    Brun, R.6    Biot, C.7
  • 16
    • 1942439085 scopus 로고    scopus 로고
    • Biomimetic chemical catalysts in the oxidative activation of drugs
    • Bernadou, J.; Meunier, B. Biomimetic chemical catalysts in the oxidative activation of drugs Adv. Synth. Catal. 2004, 346, 171-184
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 171-184
    • Bernadou, J.1    Meunier, B.2
  • 17
    • 38949125112 scopus 로고    scopus 로고
    • Hybrid molecules with a dual mode of action: Dream or reality?
    • Meunier, B. Hybrid molecules with a dual mode of action: dream or reality? Acc. Chem. Res. 2008, 41, 69-77
    • (2008) Acc. Chem. Res. , vol.41 , pp. 69-77
    • Meunier, B.1
  • 19
    • 2142781238 scopus 로고
    • The interaction of antimalarials with nucleic acids
    • Irvin, J. L.; Irvin, E. M.; Parker, F. S. The interaction of antimalarials with nucleic acids Science 1949, 110, 426-428
    • (1949) Science , vol.110 , pp. 426-428
    • Irvin, J.L.1    Irvin, E.M.2    Parker, F.S.3
  • 20
    • 0025261757 scopus 로고
    • Chloroquine as intercalator: A hypothesis revived
    • Meshnick, S. R. Chloroquine as intercalator: a hypothesis revived Parasitol. Today 1990, 6, 77-79
    • (1990) Parasitol. Today , vol.6 , pp. 77-79
    • Meshnick, S.R.1
  • 21
    • 0027497789 scopus 로고
    • Selective toxicity to malaria parasites by non-intercalating DNA-binding ligands
    • DOI 10.1016/0166-6851(93)90085-C
    • Ginsburg, H.; Nissani, E.; Krugliak, M.; Williamson, D. H. Selective toxicity to malaria parasites by non-intercalating DNA-binding ligands Mol. Biochem. Parasitol. 1993, 58, 7-15 (Pubitemid 223039618)
    • (1993) Molecular and Biochemical Parasitology , vol.58 , Issue.1 , pp. 7-15
    • Ginsburg, H.1    Nissani, E.2    Krugliak, M.3    Williamson, D.H.4
  • 22
    • 0000497582 scopus 로고
    • The interaction of chloroquine with nucleic acids and nucleoproteins
    • Parker, F. S.; Irvin, J. L. The interaction of chloroquine with nucleic acids and nucleoproteins J. Biol. Chem. 1952, 199, 897-909
    • (1952) J. Biol. Chem. , vol.199 , pp. 897-909
    • Parker, F.S.1    Irvin, J.L.2
  • 23
    • 0343865596 scopus 로고
    • Antibodies to denaturated deoxyribonucleic acid in lupus erythematosus serum. V. Mechanism of DNA-anti-DNA inhibition by chloroquine
    • Stollar, D.; Levine, L. Antibodies to denaturated deoxyribonucleic acid in lupus erythematosus serum. V. Mechanism of DNA-anti-DNA inhibition by chloroquine Arch. Biochem. Biophys. 1963, 101, 335-341
    • (1963) Arch. Biochem. Biophys. , vol.101 , pp. 335-341
    • Stollar, D.1    Levine, L.2
  • 24
    • 0004856506 scopus 로고
    • Reaction between DNA and quinacrine and other antimalarials
    • Kurnick, N. B.; Radcliffe, I. E. Reaction between DNA and quinacrine and other antimalarials J. Lab. Clin. Med.. 1962, 60, 669-688
    • (1962) J. Lab. Clin. Med. , vol.60 , pp. 669-688
    • Kurnick, N.B.1    Radcliffe, I.E.2
  • 25
    • 0019505452 scopus 로고
    • 19F-NMR chemical-shift and relaxation, optical absorption, and fluorescence studies
    • 19F-NMR chemical-shift and relaxation, optical absorption, and fluorescence studies Biopolymers 1981, 20, 435-449
    • (1981) Biopolymers , vol.20 , pp. 435-449
    • Bolton, P.H.1    Mirau, P.A.2    Shafer, R.H.3    James, T.L.4
  • 26
    • 0008344943 scopus 로고
    • DNA: Reaction with chloroquine
    • Allison, J.-L.; O'Brien, R. L.; Hahn, F. E. DNA: reaction with chloroquine Science 1965, 149, 1111-1113
    • (1965) Science , vol.149 , pp. 1111-1113
    • Allison, J.-L.1    O'Brien, R.L.2    Hahn, F.E.3
  • 27
    • 0000029821 scopus 로고
    • Spectrophotometric studies of the interaction of chloroquine with deoxyribonucleic acid
    • Cohen, S. N.; Yielding, K. L. Spectrophotometric studies of the interaction of chloroquine with deoxyribonucleic acid J. Biol. Chem. 1965, 240, 3123-3131
    • (1965) J. Biol. Chem. , vol.240 , pp. 3123-3131
    • Cohen, S.N.1    Yielding, K.L.2
  • 28
    • 33750478347 scopus 로고    scopus 로고
    • Structure-function correlation of chloroquine and analogues as transgene expression enhancers in nonviral gene delivery
    • Cheng, J.; Zeidan, R.; Mishra, S.; Liu, A.; Pun, S. H.; Kulkarni, R. P.; Jensen, G. S.; Bellocq, N. C.; Davis, M. E. Structure-function correlation of chloroquine and analogues as transgene expression enhancers in nonviral gene delivery J. Med. Chem. 2006, 49, 6522-6531
    • (2006) J. Med. Chem. , vol.49 , pp. 6522-6531
    • Cheng, J.1    Zeidan, R.2    Mishra, S.3    Liu, A.4    Pun, S.H.5    Kulkarni, R.P.6    Jensen, G.S.7    Bellocq, N.C.8    Davis, M.E.9
  • 29
    • 0020026684 scopus 로고
    • The genome of Plasmodium falciparum I: DNA base composition
    • Pollack, Y.; Katzen, A. L.; Spira, D. T.; Golenser, J. The genome of Plasmodium falciparum I: DNA base composition Nucleic Acids Res. 1982, 10 (2) 539-546
    • (1982) Nucleic Acids Res. , vol.10 , Issue.2 , pp. 539-546
    • Pollack, Y.1    Katzen, A.L.2    Spira, D.T.3    Golenser, J.4
  • 30
    • 0025070185 scopus 로고
    • Sequence preference of chloroquine binding to DNA and prevention of Z-DNA formation
    • Kwakye-Berko, F.; Meshnick, S. R. Sequence preference of chloroquine binding to DNA and prevention of Z-DNA formation Mol. Biochem. Parasitol. 1990, 39, 275-278
    • (1990) Mol. Biochem. Parasitol. , vol.39 , pp. 275-278
    • Kwakye-Berko, F.1    Meshnick, S.R.2
  • 32
    • 34249938047 scopus 로고    scopus 로고
    • Pharmacogenomic analyses of targeting the AT-rich malaria parasite genome with AT-specific alkylating drugs
    • Woynarowski, J. M.; Krugliak, M.; Ginsburg, H. Pharmacogenomic analyses of targeting the AT-rich malaria parasite genome with AT-specific alkylating drugs Mol. Biochem. Parasitol. 2007, 154, 70-81
    • (2007) Mol. Biochem. Parasitol. , vol.154 , pp. 70-81
    • Woynarowski, J.M.1    Krugliak, M.2    Ginsburg, H.3
  • 33
    • 0011763757 scopus 로고    scopus 로고
    • Reductive aminations of carbonyl compounds with borohydride and borane reducing agents
    • Baxter, E. W.; Reitz, A. B. Reductive aminations of carbonyl compounds with borohydride and borane reducing agents Organic Reactions 2004, 59, 1-57
    • (2004) Organic Reactions , vol.59 , pp. 1-57
    • Baxter, E.W.1    Reitz, A.B.2
  • 34
    • 0031054484 scopus 로고    scopus 로고
    • Enantioselective synthesis of (R)- and (S)-1-ferrocenylalkylamines. Reduction of enantiopure ferrocenylimines obtained from valinol and phenylglycinol
    • Glorian, G.; Maciejewski, L.; Brocard, J.; Agbossou, F. Enantioselective synthesis of (R)- and (S)-1-ferrocenylalkylamines. Reduction of enantiopure ferrocenylimines obtained from valinol and phenylglycinol Tetrahedron: Asymmetry 1997, 8, 355-358
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 355-358
    • Glorian, G.1    MacIejewski, L.2    Brocard, J.3    Agbossou, F.4
  • 35
    • 14644443491 scopus 로고    scopus 로고
    • A colorimetric high-throughput β-hematin inhibition screening assay for use in the search for antimalarial compounds
    • Ncokazi, K. K.; Egan, T. E. A colorimetric high-throughput β-hematin inhibition screening assay for use in the search for antimalarial compounds Anal. Biochem. 2005, 338, 306-319
    • (2005) Anal. Biochem. , vol.338 , pp. 306-319
    • Ncokazi, K.K.1    Egan, T.E.2
  • 37
    • 33748768224 scopus 로고    scopus 로고
    • Solvent-Induced Effects: Self-Association of Positively Charged π Systems
    • Buisine, E.; de Villiers, K.; Egan, T. J.; Biot, C. Solvent-Induced Effects: Self-Association of Positively Charged π Systems J. Am. Chem. Soc. 2006, 128, 12122-12128
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 12122-12128
    • Buisine, E.1    De Villiers, K.2    Egan, T.J.3    Biot, C.4
  • 40
    • 0028535425 scopus 로고
    • Gene transfer with a series of lipophilic DNA-binding molecules
    • Remy, J. S.; Sirlin, C.; Vierling, P.; Behr, J. P. Gene transfer with a series of lipophilic DNA-binding molecules Bioconjugate Chem. 1994, 5, 647-654
    • (1994) Bioconjugate Chem. , vol.5 , pp. 647-654
    • Remy, J.S.1    Sirlin, C.2    Vierling, P.3    Behr, J.P.4
  • 42
  • 45
    • 0000100330 scopus 로고    scopus 로고
    • Synthesis of NMP, a fluoxetine (Prozac) precursor, in the introductory organic laboratory
    • Perrine, D. M.; Sabanayagam, N. R.; Reynolds, K. J. Synthesis of NMP, a fluoxetine (Prozac) precursor, in the introductory organic laboratory J. Chem. Educ. 1998, 75, 1266
    • (1998) J. Chem. Educ. , vol.75 , pp. 1266
    • Perrine, D.M.1    Sabanayagam, N.R.2    Reynolds, K.J.3
  • 46
    • 77951140329 scopus 로고
    • Chemotherapeutic drugs against viruses. XXVII. Synthesis and antiviral activity of 1-(p -alkylphenyl)-3-dimethylamino-1-propanol
    • Tsuji, T.; Mizuma, T.; Toyoshima, S. Chemotherapeutic drugs against viruses. XXVII. Synthesis and antiviral activity of 1-(p -alkylphenyl)-3- dimethylamino-1-propanol Chem. Pharm. Bull. 1960, 8, 763-767
    • (1960) Chem. Pharm. Bull. , vol.8 , pp. 763-767
    • Tsuji, T.1    Mizuma, T.2    Toyoshima, S.3
  • 47
    • 0017311840 scopus 로고
    • Human malaria parasites in continuous culture
    • Trager, W.; Jensen, J. B. Human malaria parasites in continuous culture Science 1976, 193, 673-675
    • (1976) Science , vol.193 , pp. 673-675
    • Trager, W.1    Jensen, J.B.2
  • 48
    • 0018606732 scopus 로고
    • Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique
    • Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique Antimicrob. Agents Chemother. 1979, 16, 710-718
    • (1979) Antimicrob. Agents Chemother. , vol.16 , pp. 710-718
    • Desjardins, R.E.1    Canfield, C.J.2    Haynes, J.D.3    Chulay, J.D.4


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