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Volumn 79, Issue 5, 2012, Pages 819-834

Prodrugs of Acyclovir - A Computational Approach

Author keywords

Acyclovir prodrugs; Bioavailability of acyclovir; Density functional theory calculations; Intramolecular amide hydrolysis; Maleamic acid amides

Indexed keywords

ACICLOVIR; AMIDE; CARBON; PRODRUG; WATER;

EID: 84859420858     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01335.x     Document Type: Article
Times cited : (26)

References (51)
  • 1
    • 30344486584 scopus 로고    scopus 로고
    • Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy
    • de Clercq E., Field H.J. (2006) Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br J Pharmacol;147:1-11.
    • (2006) Br J Pharmacol , vol.147 , pp. 1-11
    • de Clercq, E.1    Field, H.J.2
  • 2
    • 0021089633 scopus 로고
    • Pharmacokinetics of acyclovir after intravenous and oral administration
    • de Miranda P., Blum M.R. (1983) Pharmacokinetics of acyclovir after intravenous and oral administration. J Antimicrob Chemother;12(Suppl. B):29-37.
    • (1983) J Antimicrob Chemother , vol.12 , Issue.SUPPL. B , pp. 29-37
    • de Miranda, P.1    Blum, M.R.2
  • 3
    • 0019919014 scopus 로고
    • Overview of acyclovir pharmacokinetic disposition in adults and children
    • Blum M.R., Liao S.H.T., de Miranda P. (1982) Overview of acyclovir pharmacokinetic disposition in adults and children. Am J Med;73(Suppl. 1A):186-192.
    • (1982) Am J Med , vol.73 , Issue.SUPPL. 1A , pp. 186-192
    • Blum, M.R.1    Liao, S.H.T.2    de Miranda, P.3
  • 4
    • 0036891949 scopus 로고    scopus 로고
    • Preliminary pharmacokinetic study to different preparations of acyclovir with β-cyclodextrin
    • Luengo J., Aranguiz T., Sepulveda J. (2002) Preliminary pharmacokinetic study to different preparations of acyclovir with β-cyclodextrin. J Pharm Sci;91:2593-2598.
    • (2002) J Pharm Sci , vol.91 , pp. 2593-2598
    • Luengo, J.1    Aranguiz, T.2    Sepulveda, J.3
  • 5
    • 37549034654 scopus 로고    scopus 로고
    • Influence of a niosomal formulation on the oral bioavailability of acyclovir in rabbits
    • Article 106. DOI:
    • Attia I.A., El-Gizawy S.A., Fouda M.A., Donia A.M. (2007) Influence of a niosomal formulation on the oral bioavailability of acyclovir in rabbits. AAPS Pharm Sci Tech; 8: Article 106. DOI:
    • (2007) AAPS Pharm Sci Tech , vol.8
    • Attia, I.A.1    El-Gizawy, S.A.2    Fouda, M.A.3    Donia, A.M.4
  • 6
    • 84859428411 scopus 로고    scopus 로고
    • Formulation and in vitro and in vivo characterization of acyclovir loaded mucoadhesive microspheres
    • Yadav S., Jain S., Prajapati S., Motwani M., Kumar S. (2011) Formulation and in vitro and in vivo characterization of acyclovir loaded mucoadhesive microspheres. J Pharm Sci Tech;3:441-447.
    • (2011) J Pharm Sci Tech , vol.3 , pp. 441-447
    • Yadav, S.1    Jain, S.2    Prajapati, S.3    Motwani, M.4    Kumar, S.5
  • 7
    • 0028883462 scopus 로고
    • Absolute bioavailability and metabolic disposition of valaciclovir, the l-valyl ester of acyclovir, following oral administration to humans
    • Soul-Lawton J., Seaber E., On N., Wootton R., Rolan P., Posner J. (1995) Absolute bioavailability and metabolic disposition of valaciclovir, the l-valyl ester of acyclovir, following oral administration to humans. Antimicrob Agents Chemother;39:2759-2764.
    • (1995) Antimicrob Agents Chemother , vol.39 , pp. 2759-2764
    • Soul-Lawton, J.1    Seaber, E.2    On, N.3    Wootton, R.4    Rolan, P.5    Posner, J.6
  • 8
  • 9
    • 50049105721 scopus 로고    scopus 로고
    • Analysis of Menger's spatiotemporal hypothesis
    • Karaman R. (2008) Analysis of Menger's spatiotemporal hypothesis. Tetrahedron Lett;49:5998-6002.
    • (2008) Tetrahedron Lett , vol.49 , pp. 5998-6002
    • Karaman, R.1
  • 10
    • 68049127782 scopus 로고    scopus 로고
    • Cleavage of Menger's aliphatic amide: a model for peptidase enzyme solely explained by proximity orientation in intramolecular proton transfer
    • Karaman R. (2009) Cleavage of Menger's aliphatic amide: a model for peptidase enzyme solely explained by proximity orientation in intramolecular proton transfer. J Mol Struct;910:27-33.
    • (2009) J Mol Struct , vol.910 , pp. 27-33
    • Karaman, R.1
  • 11
    • 77949489830 scopus 로고    scopus 로고
    • The efficiency of proton transfer in Kirby's enzyme model, a computational approach
    • Karaman R. (2010) The efficiency of proton transfer in Kirby's enzyme model, a computational approach. Tetrahedron Lett;51:2130-2135.
    • (2010) Tetrahedron Lett , vol.51 , pp. 2130-2135
    • Karaman, R.1
  • 12
    • 78049329519 scopus 로고    scopus 로고
    • A computational analysis of intramolecularity in proton transfer reactions
    • Karaman R., Pascal R. (2010) A computational analysis of intramolecularity in proton transfer reactions. Org Biomol Chem;8:5174-5178.
    • (2010) Org Biomol Chem , vol.8 , pp. 5174-5178
    • Karaman, R.1    Pascal, R.2
  • 13
    • 77956414921 scopus 로고    scopus 로고
    • Anti-malarial pro-drugs- a computational aided design
    • Karaman R., Hallak H. (2010) Anti-malarial pro-drugs- a computational aided design. Chem Biol Drug Des;76:350-360.
    • (2010) Chem Biol Drug Des , vol.76 , pp. 350-360
    • Karaman, R.1    Hallak, H.2
  • 14
    • 77956229171 scopus 로고    scopus 로고
    • A general equation correlating intramolecular rates with attack" parameters: distance and angle
    • Karaman R. (2010) A general equation correlating intramolecular rates with attack" parameters: distance and angle. Tetrahedron Lett;51:5185-5190.
    • (2010) Tetrahedron Lett , vol.51 , pp. 5185-5190
    • Karaman, R.1
  • 15
    • 78651287394 scopus 로고    scopus 로고
    • Prodrugs of Aza nucleosides based on proton transfer reactions
    • Karaman R. (2010) Prodrugs of Aza nucleosides based on proton transfer reactions. J Comput Aided Mol Des;24:961-970.
    • (2010) J Comput Aided Mol Des , vol.24 , pp. 961-970
    • Karaman, R.1
  • 16
    • 79251596024 scopus 로고    scopus 로고
    • Analyzing the efficiency of proton transfer to carbon in Kirby's enzyme model - a computational approach
    • Karaman R. (2011) Analyzing the efficiency of proton transfer to carbon in Kirby's enzyme model - a computational approach. Tetrahedron Lett;52:699-704.
    • (2011) Tetrahedron Lett , vol.52 , pp. 699-704
    • Karaman, R.1
  • 17
    • 84856259611 scopus 로고    scopus 로고
    • Computer-assisted design for paracetamol masking bitter taste prodrugs
    • Hejaz H., Karaman R., Khamis M. (2012) Computer-assisted design for paracetamol masking bitter taste prodrugs. J Mol Model;18:103-114.
    • (2012) J Mol Model , vol.18 , pp. 103-114
    • Hejaz, H.1    Karaman, R.2    Khamis, M.3
  • 18
    • 37049077509 scopus 로고
    • Most efficient intramolecular general acid catalysis of acetal hydrolysis by the carboxyl group
    • Kirby A.J., Parkinson A. (1994) Most efficient intramolecular general acid catalysis of acetal hydrolysis by the carboxyl group. J Chem Soc Chem Commun;707-708.
    • (1994) J Chem Soc Chem Commun , pp. 707-708
    • Kirby, A.J.1    Parkinson, A.2
  • 19
    • 0000689285 scopus 로고    scopus 로고
    • Efficiency of proton transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of dialkyl acetals of benzaldehyde
    • Brown C.J., Kirby A.J. (1997) Efficiency of proton transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of dialkyl acetals of benzaldehyde. J Chem Soc Perkin Trans;2:1081-1093.
    • (1997) J Chem Soc Perkin Trans , vol.2 , pp. 1081-1093
    • Brown, C.J.1    Kirby, A.J.2
  • 20
    • 2942723715 scopus 로고
    • The hydrolysis of substituted 2-methoxymethoxybenzoic acids
    • Craze G.-A., Kirby A.J. (1974) The hydrolysis of substituted 2-methoxymethoxybenzoic acids. J Chem Soc Perkin Trans;2:61-66.
    • (1974) J Chem Soc Perkin Trans , vol.2 , pp. 61-66
    • Craze, G.-A.1    Kirby, A.J.2
  • 21
    • 0033305805 scopus 로고    scopus 로고
    • A mechanism for efficient proton-transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of 1-arylethyl ethers of salicylic acid
    • Barber S.E., Dean K.E.S., Kirby A.J. (1999) A mechanism for efficient proton-transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of 1-arylethyl ethers of salicylic acid. Can J Chem;792-801.
    • (1999) Can J Chem , pp. 792-801
    • Barber, S.E.1    Dean, K.E.S.2    Kirby, A.J.3
  • 22
    • 33845919294 scopus 로고    scopus 로고
    • Efficient intramolecular general acid catalysis of nucleophilic attack on a phosphodiester
    • Kirby A.J., de Silva M.F., Lima D., Roussev C.D., Nome F. (2006) Efficient intramolecular general acid catalysis of nucleophilic attack on a phosphodiester. J Am Chem Soc;128:16944-16952.
    • (2006) J Am Chem Soc , vol.128 , pp. 16944-16952
    • Kirby, A.J.1    de Silva, M.F.2    Lima, D.3    Roussev, C.D.4    Nome, F.5
  • 23
    • 0006648814 scopus 로고
    • Efficient intramolecular general acid catalysis of enol ether hydrolysis. Hydrogen-bonding stabilization of the transition state for proton transfer to carbon
    • Kirby A.J., Williams N.H. (1994) Efficient intramolecular general acid catalysis of enol ether hydrolysis. Hydrogen-bonding stabilization of the transition state for proton transfer to carbon. J Chem Soc Perkin Trans;2:643-648.
    • (1994) J Chem Soc Perkin Trans , vol.2 , pp. 643-648
    • Kirby, A.J.1    Williams, N.H.2
  • 24
    • 37049067165 scopus 로고
    • Efficient intramolecular general acid catalysis of vinyl ether hydrolysis by the neighbouring carboxylic acid group
    • Kirby A.J., Williams N.H. (1991) Efficient intramolecular general acid catalysis of vinyl ether hydrolysis by the neighbouring carboxylic acid group. J Chem Soc Chem Commun;1643-1644.
    • (1991) J Chem Soc Chem Commun , pp. 1643-1644
    • Kirby, A.J.1    Williams, N.H.2
  • 25
    • 0034721416 scopus 로고    scopus 로고
    • Exploring the limits of efficiency of proton-transfer catalysis in models and enzymes
    • Hartwell E., Hodgson D.R.W., Kirby A.J. (2000) Exploring the limits of efficiency of proton-transfer catalysis in models and enzymes. J Am Chem Soc;122:9326-9327.
    • (2000) J Am Chem Soc , vol.122 , pp. 9326-9327
    • Hartwell, E.1    Hodgson, D.R.W.2    Kirby, A.J.3
  • 26
    • 0001461840 scopus 로고    scopus 로고
    • Efficiency of proton transfer catalysis in models and enzymes
    • Kirby A.J. (1997) Efficiency of proton transfer catalysis in models and enzymes. Acc Chem Res;30:290-296.
    • (1997) Acc Chem Res , vol.30 , pp. 290-296
    • Kirby, A.J.1
  • 27
    • 12444319339 scopus 로고    scopus 로고
    • The search for efficient intramolecular proton transfer from carbon: the kinetically silent intramolecular general base-catalysed elimination reaction of o-phenyl 8-dimethylamino-1-naphthaldoximes
    • Asaad N., Davies J.E., Hodgson D.R.W., Kirby A.J. (2005) The search for efficient intramolecular proton transfer from carbon: the kinetically silent intramolecular general base-catalysed elimination reaction of o-phenyl 8-dimethylamino-1-naphthaldoximes. J Phys Org Chem;18:101-109.
    • (2005) J Phys Org Chem , vol.18 , pp. 101-109
    • Asaad, N.1    Davies, J.E.2    Hodgson, D.R.W.3    Kirby, A.J.4
  • 28
    • 0025332917 scopus 로고
    • Remote enzyme-coupled amine release
    • Menger F.M., Ladika M. (1990) Remote enzyme-coupled amine release. J Org Chem;35:3006-3007.
    • (1990) J Org Chem , vol.35 , pp. 3006-3007
    • Menger, F.M.1    Ladika, M.2
  • 29
    • 33845279420 scopus 로고
    • Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model
    • Menger F.M., Ladika M. (1988) Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model. J Am Chem Soc;110:6794-6796.
    • (1988) J Am Chem Soc , vol.110 , pp. 6794-6796
    • Menger, F.M.1    Ladika, M.2
  • 30
    • 0001617183 scopus 로고
    • On the source of intramolecular and enzymatic reactivity
    • Menger F.M. (1985) On the source of intramolecular and enzymatic reactivity. Acc Chem Res;18:128-134.
    • (1985) Acc Chem Res , vol.18 , pp. 128-134
    • Menger, F.M.1
  • 31
    • 0020793406 scopus 로고
    • Directionality of proton transfer in solution. Three systems of known angularity
    • Menger F.M., Chow J.F., Kaiserman H., Vasquez P.C. (1983) Directionality of proton transfer in solution. Three systems of known angularity. J Am Chem Soc;105:4996-5002.
    • (1983) J Am Chem Soc , vol.105 , pp. 4996-5002
    • Menger, F.M.1    Chow, J.F.2    Kaiserman, H.3    Vasquez, P.C.4
  • 32
    • 0000004640 scopus 로고
    • Directionality of organic reactions in solution
    • Menger F.M. (1983) Directionality of organic reactions in solution. Tetrahedron;39:1013-1040.
    • (1983) Tetrahedron , vol.39 , pp. 1013-1040
    • Menger, F.M.1
  • 33
    • 2142675204 scopus 로고
    • Transition-state pliability in nitrogen-to-nitrogen proton transfer
    • Menger F.M., Grosssman J., Liotta D.C. (1983) Transition-state pliability in nitrogen-to-nitrogen proton transfer. J Org Chem;48:905-907.
    • (1983) J Org Chem , vol.48 , pp. 905-907
    • Menger, F.M.1    Grosssman, J.2    Liotta, D.C.3
  • 35
    • 28544453067 scopus 로고    scopus 로고
    • An alternative view of enzyme catalysis
    • references therein.
    • Menger F.M. (2005) An alternative view of enzyme catalysis. Pure Appl Chem;77:1873-1876 and references therein.
    • (2005) Pure Appl Chem , vol.77 , pp. 1873-1876
    • Menger, F.M.1
  • 36
    • 37049120339 scopus 로고
    • Structure and efficiency in intramolecular and enzymatic catalysis. Catalysis of amide hydrolysis by the carboxy-group of substituted maleamic acids
    • Kirby A.J., Lancaster P.W. (1972) Structure and efficiency in intramolecular and enzymatic catalysis. Catalysis of amide hydrolysis by the carboxy-group of substituted maleamic acids. J Chem Soc Perkin Trans;2:1206-1214.
    • (1972) J Chem Soc Perkin Trans , vol.2 , pp. 1206-1214
    • Kirby, A.J.1    Lancaster, P.W.2
  • 38
    • 0039968228 scopus 로고
    • Application of a universal force field to main group compounds
    • Casewit C.J., Colwell K.S., Rappe' A.K. (1992) Application of a universal force field to main group compounds. J Am Chem Soc;114:10046-10053.
    • (1992) J Am Chem Soc , vol.114 , pp. 10046-10053
    • Casewit, C.J.1    Colwell, K.S.2    Rappe', A.K.3
  • 39
    • 65249096094 scopus 로고    scopus 로고
    • The DBH24/08 database and its use to assess electronic structure model chemistries for chemical reaction barrier heights
    • Zheng J., Zhao Y., Truhlar D.G. (2009) The DBH24/08 database and its use to assess electronic structure model chemistries for chemical reaction barrier heights. J Chem Theory Comput;5:808-821.
    • (2009) J Chem Theory Comput , vol.5 , pp. 808-821
    • Zheng, J.1    Zhao, Y.2    Truhlar, D.G.3
  • 40
  • 41
    • 0002122384 scopus 로고
    • Reaction paths on multidimensional energy hypersurfaces
    • Muller K. (1980) Reaction paths on multidimensional energy hypersurfaces. Angew Chem Int Ed Engl;19:1-13.
    • (1980) Angew Chem Int Ed Engl , vol.19 , pp. 1-13
    • Muller, K.1
  • 42
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics
    • Cancès M.T., Mennucci B., Tomasi J. (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys;107:3032-3041.
    • (1997) J Chem Phys , vol.107 , pp. 3032-3041
    • Cancès, M.T.1    Mennucci, B.2    Tomasi, J.3
  • 43
    • 84961979198 scopus 로고    scopus 로고
    • Continuum solvation models: a new approach to the problem of solute's charge distribution and cavity boundaries
    • Mennucci B., Tomasi J. (1997) Continuum solvation models: a new approach to the problem of solute's charge distribution and cavity boundaries. J Chem Phys;106:5151.
    • (1997) J Chem Phys , vol.106 , pp. 5151
    • Mennucci, B.1    Tomasi, J.2
  • 44
    • 0031553301 scopus 로고    scopus 로고
    • Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications
    • Mennucci B., Cancès M.T., Tomasi J. (1997) Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications. J Phys Chem B;101:10506-10517.
    • (1997) J Phys Chem B , vol.101 , pp. 10506-10517
    • Mennucci, B.1    Cancès, M.T.2    Tomasi, J.3
  • 45
    • 84962428823 scopus 로고    scopus 로고
    • The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level
    • Tomasi J., Mennucci B., Cancès M.T. (1997) The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J Mol Struct;464:211-226.
    • (1997) J Mol Struct , vol.464 , pp. 211-226
    • Tomasi, J.1    Mennucci, B.2    Cancès, M.T.3
  • 46
    • 0014325267 scopus 로고
    • Reversible blocking of amino groups with citraconic anhydride
    • Dixon H.B.F., Perham R.N. (1968) Reversible blocking of amino groups with citraconic anhydride. Biochem J;109:312-314.
    • (1968) Biochem J , vol.109 , pp. 312-314
    • Dixon, H.B.F.1    Perham, R.N.2
  • 47
    • 0038564213 scopus 로고
    • Carboxylic acid participation in amide hydrolysis. Evidence that separation of a nonbonded complex can be rate determining
    • Kluger R., Chin J. (1982) Carboxylic acid participation in amide hydrolysis. Evidence that separation of a nonbonded complex can be rate determining. J Am Chem Soc;104:2891-2897.
    • (1982) J Am Chem Soc , vol.104 , pp. 2891-2897
    • Kluger, R.1    Chin, J.2
  • 48
    • 84986431729 scopus 로고
    • AM1 study of acid-catalyzed hydrolysis of maleamic (4-amino-4-oxo-2-butenoic) acids
    • Katagi T. (1990) AM1 study of acid-catalyzed hydrolysis of maleamic (4-amino-4-oxo-2-butenoic) acids. J Comb Chem;11:1094-1100.
    • (1990) J Comb Chem , vol.11 , pp. 1094-1100
    • Katagi, T.1
  • 49
    • 84555202654 scopus 로고    scopus 로고
    • Analyzing the efficiency in intramolecular amide hydrolysis of Kirby's N-alkylmaleamic acids - a computational approach
    • Karaman R. (2011) Analyzing the efficiency in intramolecular amide hydrolysis of Kirby's N-alkylmaleamic acids - a computational approach. Comput Theor Chem;974:133-142.
    • (2011) Comput Theor Chem , vol.974 , pp. 133-142
    • Karaman, R.1
  • 51
    • 84855186054 scopus 로고    scopus 로고
    • Effective molarities for intramolecular reactions
    • Kirby A.J. (2005) Effective molarities for intramolecular reactions. J Phys Org Chem;18:101-278.
    • (2005) J Phys Org Chem , vol.18 , pp. 101-278
    • Kirby, A.J.1


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