메뉴 건너뛰기




Volumn 26, Issue 12, 2013, Pages 1801-1809

Methemoglobin generation by 8-aminoquinolines: Effect of substitution at 5-position of primaquine

Author keywords

[No Author keywords available]

Indexed keywords

4 (6 METHOXY 8 QUINOLYLAMINO)VALERIC ACID; 5 HYDROXYPRIMAQUINE; 5,6 DIHYDROXYPRIMAQUINE; 6 METHOXY 8 ( N HYDROXY)AMINOQUINOLINE; 8 AMINO 6 METHOXYQUINOLINE; AMINOQUINOLINE DERIVATIVE; ANTIMALARIAL AGENT; METHEMOGLOBIN; NITRIC OXIDE SYNTHASE; PRIMAQUINE DERIVATIVE; UNCLASSIFIED DRUG; 8-AMINOQUINOLINE; PRIMAQUINE;

EID: 84890476905     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400067a     Document Type: Article
Times cited : (6)

References (55)
  • 1
    • 7644226738 scopus 로고    scopus 로고
    • Primaquine therapy for malaria
    • DOI 10.1086/424663
    • Baird, J. K. and Hoffman, S. L. (2004) Primaquine therapy for malaria Clin. Infect. Dis. 39, 1336-1345 (Pubitemid 39458520)
    • (2004) Clinical Infectious Diseases , vol.39 , Issue.9 , pp. 1336-1345
    • Baird, J.K.1    Hoffman, S.L.2
  • 2
    • 84870321438 scopus 로고    scopus 로고
    • Diagnosis and Treatment of Plasmodium vivax Malaria
    • Baird, K. J., Maguire, J. D., and Price, R. N. (2012) Diagnosis and Treatment of Plasmodium vivax Malaria Adv. Parasitol. 80, 203-270
    • (2012) Adv. Parasitol. , vol.80 , pp. 203-270
    • Baird, K.J.1    Maguire, J.D.2    Price, R.N.3
  • 4
    • 83255188683 scopus 로고    scopus 로고
    • Review: Improving the Therapeutic Index of 8-Aminoquinolines by the Use of Drug Combinations: Review of the Literature and Proposal for Future Investigations
    • Myint, H. Y., Berman, J., Walker, L., Pybus, B., Melendez, V., Baird, J. K., and Ohrt, C. (2011) Review: Improving the Therapeutic Index of 8-Aminoquinolines by the Use of Drug Combinations: Review of the Literature and Proposal for Future Investigations Am. J. Trop. Med. Hyg. 85, 1010-1014
    • (2011) Am. J. Trop. Med. Hyg. , vol.85 , pp. 1010-1014
    • Myint, H.Y.1    Berman, J.2    Walker, L.3    Pybus, B.4    Melendez, V.5    Baird, J.K.6    Ohrt, C.7
  • 5
    • 60549099364 scopus 로고    scopus 로고
    • Primaquine revisited six decades after its discovery
    • Vale, N., Moreira, R., and Gomes, P. (2009) Primaquine revisited six decades after its discovery Eur. J. Med. Chem. 44, 937-953
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 937-953
    • Vale, N.1    Moreira, R.2    Gomes, P.3
  • 6
    • 0034118394 scopus 로고    scopus 로고
    • A simple and rapid evaluation of methemoglobin toxicity of 8- aminoquinolines and related compounds
    • DOI 10.1006/eesa.1999.1868
    • Srivastava, P., Singh, S., Jain, G. K., Puri, S. K., and Pandey, V. C. (2000) A Simple and Rapid Evaluation of Methemoglobin Toxicity of 8-Aminoquinolines and Related Compounds Ecotoxicol. Environ. Saf. 45, 236-239 (Pubitemid 30154585)
    • (2000) Ecotoxicology and Environmental Safety , vol.45 , Issue.3 , pp. 236-239
    • Srivastava, P.1    Singh, S.2    Jain, G.K.3    Puri, S.K.4    Pandey, V.C.5
  • 8
    • 1642292958 scopus 로고    scopus 로고
    • Primaquine-Induced Hemolytic Anemia: Susceptibility of Normal versus Glutathione-Depleted Rat Erythrocytes to 5-Hydroxyprimaquine
    • DOI 10.1124/jpet.103.062984
    • Bowman, Z. S., Oatis, J. E., Whelan, J. L., Jollow, D. J., and McMillan, D. C. (2004) Primaquine-Induced Hemolytic Anemia: Susceptibility of Normal versus Glutathione-Depleted Rat Erythrocytes to 5-Hydroxyprimaquine J. Pharmacol. Exp. Ther. 309, 79-85 (Pubitemid 38393117)
    • (2004) Journal of Pharmacology and Experimental Therapeutics , vol.309 , Issue.1 , pp. 79-85
    • Bowman, Z.S.1    Oatis Jr., J.E.2    Whelan, J.L.3    Jollow, D.J.4    McMillan, D.C.5
  • 9
    • 27744536997 scopus 로고    scopus 로고
    • Primaquine-induced hemolytic anemia: Role of splenic macrophages in the fate of 5-hydroxyprimaquine-treated rat erythrocytes
    • DOI 10.1124/jpet.105.090407
    • Bowman, Z. S., Jollow, D. J., and McMillan, D. C. (2005) Primaquine-Induced Hemolytic Anemia: Role of Splenic Macrophages in the Fate of 5-Hydroxyprimaquine-Treated Rat Erythrocytes J. Pharmacol. Exp. Ther. 315, 980-986 (Pubitemid 41635383)
    • (2005) Journal of Pharmacology and Experimental Therapeutics , vol.315 , Issue.3 , pp. 980-986
    • Bowman, Z.S.1    Jollow, D.J.2    McMillan, D.C.3
  • 10
    • 0026630568 scopus 로고
    • Hydroxylated metabolites of the antimalarial drug primaquine. Oxidation and redox cycling
    • Vasquez-Vivar, J. and Augusto, O. (1992) Hydroxylated metabolites of the antimalarial drug primaquine. Oxidation and redox cycling J. Biol. Chem. 267, 6848-6854
    • (1992) J. Biol. Chem. , vol.267 , pp. 6848-6854
    • Vasquez-Vivar, J.1    Augusto, O.2
  • 11
    • 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., and Jollow, D. J. (2001) Primaquine-Induced Hemolytic Anemia: Formation and Hemotoxicity of the Arylhydroxylamine Metabolite 6-Methoxy-8-hydroxylaminoquinoline J. Pharmacol. Exp. Ther. 297, 509-515 (Pubitemid 32377979)
    • (2001) Journal of Pharmacology and Experimental Therapeutics , vol.297 , Issue.2 , pp. 509-515
    • Bolchoz, L.J.C.1    Budinsky, R.A.2    Mcmillan, D.C.3    Jollow, D.J.4
  • 12
    • 0036896929 scopus 로고    scopus 로고
    • Primaquine-induced hemolytic anemia: Formation of free radicals in rat erythrocytes exposed to 6-methoxy-8-hydroxylaminoquinoline
    • DOI 10.1124/jpet.102.041459
    • Bolchoz, L. J. C., Gelasco, A. K., Jollow, D. J., and McMillan, D. C. (2002) Primaquine-Induced Hemolytic Anemia: Formation of Free Radicals in Rat Erythrocytes Exposed to 6-Methoxy-8-hydroxylaminoquinoline J. Pharmacol. Exp. Ther. 303, 1121-1129 (Pubitemid 35424397)
    • (2002) Journal of Pharmacology and Experimental Therapeutics , vol.303 , Issue.3 , pp. 1121-1129
    • Bolchoz, L.J.C.1    Gelasco, A.K.2    Jollow, D.J.3    McMillan, D.C.4
  • 13
    • 0028047135 scopus 로고
    • Oxidative activity of primaquine metabolites on rat erythrocytes in vitro and in vivo
    • DOI 10.1016/0006-2952(94)90022-1
    • Vásquez-Vivar, J. and Augusto, O. (1994) Oxidative activity of primaquine metabolites on rat erythrocytes in vitro and in vivo Biochem. Pharmacol. 47, 309-316 (Pubitemid 24050889)
    • (1994) Biochemical Pharmacology , vol.47 , Issue.2 , pp. 309-316
    • Vasquez-Vivar, J.1    Augusto, O.2
  • 14
    • 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., Paixao, P., Moreira, R., Portela, M. J., Do Rosario, V. E., and Iley, J. (1999) 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. 51, 299-303 (Pubitemid 29334356)
    • (1999) Experimental and Toxicologic Pathology , vol.51 , Issue.4-5 , pp. 299-303
    • Constantino, L.1    Paixao, P.2    Moreira, R.3    Portela, M.J.4    Do Rosario, V.E.5    Iley, J.6
  • 15
    • 0025916444 scopus 로고
    • The conversion of primaquine into primaquine-aldehyde, primaquine-alcohol, and carboxyprimaquine, a major plasma metabolite
    • Frischer, H., Mellovitz, R. L., Ahmad, T., and Nora, M. V. (1991) The conversion of primaquine into primaquine-aldehyde, primaquine-alcohol, and carboxyprimaquine, a major plasma metabolite J. Lab. Clin. Med. 117, 468-476
    • (1991) J. Lab. Clin. Med. , vol.117 , pp. 468-476
    • Frischer, H.1    Mellovitz, R.L.2    Ahmad, T.3    Nora, M.V.4
  • 16
    • 0022342389 scopus 로고
    • Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolysates
    • DOI 10.1016/0041-008X(85)90155-3
    • Link, C. M., Theoharides, A. D., Anders, J. C., Chung, H., and Canfield, C. J. (1985) Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolysates Toxicol. Appl. Pharmacol. 81, 192-202 (Pubitemid 16204105)
    • (1985) Toxicology and Applied Pharmacology , vol.81 , Issue.2 , pp. 192-202
    • Link, C.M.1    Theoharides, A.D.2    Anders, J.C.3
  • 17
    • 79953906869 scopus 로고    scopus 로고
    • Extended side chain analogues of 8-aminoquinolines: Synthesis and evaluation of antiprotozoal, antimicrobial, β-hematin inhibition, and cytotoxic activities
    • Kaur, K., Jain, M., Khan, S. I., Jacob, M. R., Tekwani, B. L., Singh, S., Singh, P. P., and Jain, R. (2011) Extended side chain analogues of 8-aminoquinolines: Synthesis and evaluation of antiprotozoal, antimicrobial, β-hematin inhibition, and cytotoxic activities MedChemComm 2, 300-307
    • (2011) MedChemComm , vol.2 , pp. 300-307
    • Kaur, K.1    Jain, M.2    Khan, S.I.3    Jacob, M.R.4    Tekwani, B.L.5    Singh, S.6    Singh, P.P.7    Jain, R.8
  • 19
    • 44449113132 scopus 로고    scopus 로고
    • Antiparasitic activities and toxicities of individual enantiomers of the 8-aminoquinoline 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3,4- dichlorophenoxy]quinoline succinate
    • DOI 10.1128/AAC.00645-07
    • Nanayakkara, N. P. D., Ager, A. L., Jr., Bartlett, M. S., Yardley, V., Croft, S. L., Khan, I. A., McChesney, J. D., and Walker, L. A. (2008) Antiparasitic Activities and Toxicities of Individual Enantiomers of the 8-Aminoquinoline 8-[(4-Amino-1-Methylbutyl)Amino]-6-Methoxy-4-Methyl-5-[3,4- Dichlorophenoxy]Quinoline Succinate Antimicrob. Agents Chemother. 52, 2130-2137 (Pubitemid 351758550)
    • (2008) Antimicrobial Agents and Chemotherapy , vol.52 , Issue.6 , pp. 2130-2137
    • Nanayakkara, N.P.D.1    Ager Jr., A.L.2    Bartlett, M.S.3    Yardley, V.4    Croft, S.L.5    Khan, I.A.6    McChesney, J.D.7    Walker, L.A.8
  • 24
    • 79952804083 scopus 로고    scopus 로고
    • Road Towards New Antimalarials - Overview of the Strategies and their Chemical Progress
    • Wu, T., Nagle, A. S., and Chatterjee, A. K. (2011) Road Towards New Antimalarials-Overview of the Strategies and their Chemical Progress Curr. Med. Chem. 18, 853-871
    • (2011) Curr. Med. Chem. , vol.18 , pp. 853-871
    • Wu, T.1    Nagle, A.S.2    Chatterjee, A.K.3
  • 25
    • 80053044417 scopus 로고    scopus 로고
    • DFT Study on the Radical Anions Formed by Primaquine and Its Derivatives
    • Liu, H., Walker, L. A., and Doerksen, R. J. (2011) DFT Study on the Radical Anions Formed by Primaquine and Its Derivatives Chem. Res. Toxicol. 24, 1476-1485
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 1476-1485
    • Liu, H.1    Walker, L.A.2    Doerksen, R.J.3
  • 26
    • 84880885931 scopus 로고    scopus 로고
    • Effect of antimalarial drug primaquine and its derivatives on the ionization potential of hemoglobin: A QM/MM study
    • Liu, H., Ding, Y., Walker, L. A., and Doerksen, R. J. (2013) Effect of antimalarial drug primaquine and its derivatives on the ionization potential of hemoglobin: A QM/MM study MedChemComm 4, 1145-1147
    • (2013) MedChemComm , vol.4 , pp. 1145-1147
    • Liu, H.1    Ding, Y.2    Walker, L.A.3    Doerksen, R.J.4
  • 27
    • 79551706067 scopus 로고    scopus 로고
    • Methemoglobinemia Caused by 8-Aminoquinoline Drugs: DFT Calculations Suggest an Analogy to H4B's Role in Nitric Oxide Synthase
    • Liu, H., Walker, L. A., Nanayakkara, N. P. D., and Doerksen, R. J. (2011) Methemoglobinemia Caused by 8-Aminoquinoline Drugs: DFT Calculations Suggest an Analogy to H4B's Role in Nitric Oxide Synthase J. Am. Chem. Soc. 133, 1172-1175
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 1172-1175
    • Liu, H.1    Walker, L.A.2    Nanayakkara, N.P.D.3    Doerksen, R.J.4
  • 28
    • 0034739024 scopus 로고    scopus 로고
    • The role of tetrahydrobiopterin in the activation of oxygen by nitric-oxide synthase
    • Bec, N., Gorren, A. F. C., Mayer, B., Schmidt, P. P., Andersson, K. K., and Lange, R. (2000) The role of tetrahydrobiopterin in the activation of oxygen by nitric-oxide synthase J. Inorg. Biochem. 81, 207-211
    • (2000) J. Inorg. Biochem. , vol.81 , pp. 207-211
    • Bec, N.1    Gorren, A.F.C.2    Mayer, B.3    Schmidt, P.P.4    Andersson, K.K.5    Lange, R.6
  • 29
    • 61749083669 scopus 로고    scopus 로고
    • First half-reaction mechanism of nitric oxide synthase: The role of proton and oxygen coupled electron transfer in the reaction by quantum mechanics/molecular mechanics
    • Cho, K.-B., Carvajal, M. A., and Shaik, S. (2008) First half-reaction mechanism of nitric oxide synthase: The role of proton and oxygen coupled electron transfer in the reaction by quantum mechanics/molecular mechanics J. Phys. Chem. B 113, 336-346
    • (2008) J. Phys. Chem. B , vol.113 , pp. 336-346
    • Cho, K.-B.1    Carvajal, M.A.2    Shaik, S.3
  • 30
    • 33947386582 scopus 로고    scopus 로고
    • Compound I of nitric oxide synthase: The active site protonation state
    • DOI 10.1021/ja066662r
    • Cho, K.-B., Derat, E., and Shaik, S. (2007) Compound I of nitric oxide synthase: The active site protonation state J. Am. Chem. Soc. 129, 3182-3188 (Pubitemid 46449351)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.11 , pp. 3182-3188
    • Cho, K.-B.1    Derat, E.2    Shaik, S.3
  • 31
    • 0033619713 scopus 로고    scopus 로고
    • Formation of a Pterin Radical in the Reaction of the Heme Domain of Inducible Nitric Oxide Synthase with Oxygen
    • Hurshman, A. R., Krebs, C., Edmondson, D. E., Huynh, B. H., and Marletta, M. A. (1999) Formation of a Pterin Radical in the Reaction of the Heme Domain of Inducible Nitric Oxide Synthase with Oxygen Biochemistry 38, 15689-15696
    • (1999) Biochemistry , vol.38 , pp. 15689-15696
    • Hurshman, A.R.1    Krebs, C.2    Edmondson, D.E.3    Huynh, B.H.4    Marletta, M.A.5
  • 32
    • 0037066114 scopus 로고    scopus 로고
    • Reactions catalyzed by the heme domain of inducible nitric oxide synthase: Evidence for the involvement of tetrahydrobiopterin in electron transfer
    • DOI 10.1021/bi012002h
    • Hurshman, A. R. and Marletta, M. A. (2002) Reactions Catalyzed by the Heme Domain of Inducible Nitric Oxide Synthase: Evidence for the Involvement of Tetrahydrobiopterin in Electron Transfer Biochemistry 41, 3439-3456 (Pubitemid 34214043)
    • (2002) Biochemistry , vol.41 , Issue.10 , pp. 3439-3456
    • Hurshman, A.R.1    Marletta, M.A.2
  • 34
    • 0035808315 scopus 로고    scopus 로고
    • Rapid kinetic studies link tetrahydrobiopterin radical formation to heme-dioxy reduction and arginine hydroxylation in inducible nitric-oxide synthase
    • DOI 10.1074/jbc.M008441200
    • Wei, C.-C., Wang, Z.-Q., Wang, Q., Meade, A. L., Hemann, C., Hille, R., and Stuehr, D. J. (2001) Rapid Kinetic Studies Link Tetrahydrobiopterin Radical Formation to Heme-dioxy Reduction and Arginine Hydroxylation in Inducible Nitric-oxide Synthase J. Biol. Chem. 276, 315-319 (Pubitemid 32050321)
    • (2001) Journal of Biological Chemistry , vol.276 , Issue.1 , pp. 315-319
    • Wei, C.-C.1    Wang, Z.-Q.2    Wang, Q.3    Meade, A.L.4    Hemann, C.5    Hille, R.6    Stuehr, D.J.7
  • 35
    • 34249821051 scopus 로고    scopus 로고
    • The Janus nature of heme
    • DOI 10.1039/b604195g
    • Poulos, T. L. (2007) The Janus nature of heme Nat. Prod. Rep. 24, 504-510 (Pubitemid 46848714)
    • (2007) Natural Product Reports , vol.24 , Issue.3 , pp. 504-510
    • Poulos, T.L.1
  • 36
    • 77349115125 scopus 로고    scopus 로고
    • P450 Enzymes: Their Structure, Reactivity, and Selectivity - Modeled by QM/MM Calculations
    • Shaik, S., Cohen, S., Wang, Y., Chen, H., Kumar, D., and Thiel, W. (2009) P450 Enzymes: Their Structure, Reactivity, and Selectivity-Modeled by QM/MM Calculations Chem. Rev. 110, 949-1017
    • (2009) Chem. Rev. , vol.110 , pp. 949-1017
    • Shaik, S.1    Cohen, S.2    Wang, Y.3    Chen, H.4    Kumar, D.5    Thiel, W.6
  • 37
    • 21944432511 scopus 로고    scopus 로고
    • Theoretical perspective on the structure and mechanism of cytochrome P450 enzymes
    • DOI 10.1021/cr030722j
    • Shaik, S., Kumar, D., de Visser, S. P., Altun, A., and Thiel, W. (2005) Theoretical Perspective on the Structure and Mechanism of Cytochrome P450 Enzymes Chem. Rev. 105, 2279-2328 (Pubitemid 40947949)
    • (2005) Chemical Reviews , vol.105 , Issue.6 , pp. 2279-2328
    • Shaik, S.1    Kumar, D.2    De Visser, S.P.3    Altun, A.4    Thiel, W.5
  • 38
    • 0034712677 scopus 로고    scopus 로고
    • Structures of the N(ω)-hydroxy-L-arginine complex of inducible nitric oxide synthase oxygenase dimer with active and inactive pterins
    • DOI 10.1021/bi992409a
    • ω-Hydroxy-L-Arginine Complex of Inducible Nitric Oxide Synthase Oxygenase Dimer with Active and Inactive Pterins Biochemistry 39, 4608-4621 (Pubitemid 30225324)
    • (2000) Biochemistry , vol.39 , Issue.16 , pp. 4608-4621
    • Crane, B.R.1    Arvai, A.S.2    Ghosh, S.3    Getzoff, E.D.4    Stuehr, D.J.5    Tainer, J.A.6
  • 39
    • 33747598937 scopus 로고    scopus 로고
    • The role of tetrahydrobiopterin in catalysis by nitric oxide synthase
    • DOI 10.1039/b607426j
    • Morao, I., Periyasamy, G., Hillier, I. H., and Joule, J. A. (2006) The role of tetrahydrobiopterin in catalysis by nitric oxide synthase Chem. Commun. (Cambridge) 3525-3527 (Pubitemid 44267670)
    • (2006) Chemical Communications , Issue.33 , pp. 3525-3527
    • Morao, I.1    Periyasamy, G.2    Hillier, I.H.3    Joule, J.A.4
  • 40
    • 0037458745 scopus 로고    scopus 로고
    • Redox properties of human endothelial nitric-oxide synthase oxygenase and reductase domains purified from yeast expression system
    • DOI 10.1074/jbc.M209606200
    • Du, M., Yeh, H.-C., Berka, V., Wang, L.-H., and Tsai, A.-L. (2003) Redox Properties of Human Endothelial Nitric-oxide Synthase Oxygenase and Reductase Domains Purified from Yeast Expression System J. Biol. Chem. 278, 6002-6011 (Pubitemid 36800850)
    • (2003) Journal of Biological Chemistry , vol.278 , Issue.8 , pp. 6002-6011
    • Du, M.1    Yeh, H.-C.2    Berka, V.3    Wang, L.-H.4    Tsai, A.-L.5
  • 41
    • 0034852561 scopus 로고    scopus 로고
    • Formation of a protonated trihydrobiopterin radical cation in the first reaction cycle of neuronal and endothelial nitric oxide synthase detected by electron paramagnetic resonance spectroscopy
    • DOI 10.1007/s007750000185
    • Schmidt, P. P., Lange, R., Gorren, A. C. F., Werner, E. R., Mayer, B., and Andersson, K. K. (2001) Formation of a protonated trihydrobiopterin radical cation in the first reaction cycle of neuronal and endothelial nitric oxide synthase detected by electron paramagnetic resonance spectroscopy J. Biol. Inorg. Chem. 6, 151-158 (Pubitemid 32822144)
    • (2001) Journal of Biological Inorganic Chemistry , vol.6 , Issue.2 , pp. 151-158
    • Schmidt, P.P.1    Lange, R.2    Gorren, A.C.F.3    Werner, E.R.4    Mayer, B.5    Andersson, K.K.6
  • 42
    • 77955837630 scopus 로고    scopus 로고
    • Nitric Oxide Synthase Stabilizes the Tetrahydrobiopterin Cofactor Radical by Controlling Its Protonation State
    • Stoll, S., NejatyJahromy, Y., Woodward, J. J., Ozarowski, A., Marletta, M. A., and Britt, R. D. (2010) Nitric Oxide Synthase Stabilizes the Tetrahydrobiopterin Cofactor Radical by Controlling Its Protonation State J. Am. Chem. Soc. 132, 11812-11823
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11812-11823
    • Stoll, S.1    Nejatyjahromy, Y.2    Woodward, J.J.3    Ozarowski, A.4    Marletta, M.A.5    Britt, R.D.6
  • 43
    • 84890509742 scopus 로고    scopus 로고
    • Schrödinger, LLC, New York, NY.
    • (2008) QSite, Schrödinger, LLC, New York, NY.
    • (2008) QSite
  • 44
    • 79954560416 scopus 로고    scopus 로고
    • DFT and Ab Initio Study of Iron-Oxo Porphyrins: May They Have a Low-Lying Iron(V)-Oxo Electromer?
    • Radon, M., Broclawik, E., and Pierloot, K. (2011) DFT and Ab Initio Study of Iron-Oxo Porphyrins: May They Have a Low-Lying Iron(V)-Oxo Electromer? J. Chem. Theory Comput. 7, 898-908
    • (2011) J. Chem. Theory Comput. , vol.7 , pp. 898-908
    • Radon, M.1    Broclawik, E.2    Pierloot, K.3
  • 45
    • 57249092727 scopus 로고    scopus 로고
    • 2 to Heme by Density Functional and Multireference ab Initio Calculations
    • 2 to Heme by Density Functional and Multireference ab Initio Calculations J. Phys. Chem. A 112, 11824-11832
    • (2008) J. Phys. Chem. A , vol.112 , pp. 11824-11832
    • Radon, M.1    Pierloot, K.2
  • 46
    • 76249097183 scopus 로고    scopus 로고
    • 7 Complexes in Heme and Non-Heme Architectures: A Density Functional and Multireference ab Initio Study
    • 7 Complexes in Heme and Non-Heme Architectures: A Density Functional and Multireference ab Initio Study J. Phys. Chem. B 114, 1518-1528
    • (2010) J. Phys. Chem. B , vol.114 , pp. 1518-1528
    • Radon, M.1    Broclawik, E.2    Pierloot, K.3
  • 47
    • 0035836323 scopus 로고    scopus 로고
    • Left-right correlation energy
    • DOI 10.1080/00268970010018431
    • Handy, N. C. and Cohen, A. J. (2001) Left-right correlation energy Mol. Phys. 99, 403-412 (Pubitemid 35227669)
    • (2001) Molecular Physics , vol.99 , Issue.5 , pp. 403-412
    • Handy, N.C.1    Cohen, A.J.2
  • 48
    • 84855634330 scopus 로고    scopus 로고
    • Schrodinger, New York, NY.
    • (2009) MacroModel, Schrodinger, New York, NY.
    • (2009) MacroModel
  • 49
    • 77952415408 scopus 로고    scopus 로고
    • Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field
    • Shivakumar, D., Williams, J., Wu, Y. J., Damm, W., Shelley, J., and Sherman, W. (2010) Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field J. Chem. Theory Comput. 6, 1509-1519
    • (2010) J. Chem. Theory Comput. , vol.6 , pp. 1509-1519
    • Shivakumar, D.1    Williams, J.2    Wu, Y.J.3    Damm, W.4    Shelley, J.5    Sherman, W.6
  • 50
    • 84874892045 scopus 로고    scopus 로고
    • Maestro-Desmond Interoperability Tools, version 3.0, Schrödinger, New York, NY.
    • (2011) Desmond Molecular Dynamics System, version 3.0, Maestro-Desmond Interoperability Tools, version 3.0, Schrödinger, New York, NY.
    • (2011) Desmond Molecular Dynamics System, Version 3.0
  • 52
    • 34250817103 scopus 로고
    • A new mixing of Hartree-Fock and local density-functional theories
    • Becke, A. D. (1993) A new mixing of Hartree-Fock and local density-functional theories J. Chem. Phys. 98, 1372-1377
    • (1993) J. Chem. Phys. , vol.98 , pp. 1372-1377
    • Becke, A.D.1
  • 53
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A. D. (1993) Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98, 5648-5652
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 54
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C., Yang, W., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 37, 785-789
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 55
    • 84857798694 scopus 로고    scopus 로고
    • Understanding the mechanisms for metabolism-linked hemolytic toxicity of primaquine against glucose 6-phosphate dehydrogenase deficient human erythrocytes: Evaluation of eryptotic pathway
    • Ganesan, S., Chaurasiya, N. D., Sahu, R., Walker, L. A., and Tekwani, B. L. (2012) Understanding the mechanisms for metabolism-linked hemolytic toxicity of primaquine against glucose 6-phosphate dehydrogenase deficient human erythrocytes: Evaluation of eryptotic pathway Toxicology 294, 54-60
    • (2012) Toxicology , vol.294 , pp. 54-60
    • Ganesan, S.1    Chaurasiya, N.D.2    Sahu, R.3    Walker, L.A.4    Tekwani, B.L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.