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Volumn 52, Issue 4, 2010, Pages 508-516

Hydrophobicity/hydrophilicity descriptors obtained from extrapolated chromatographic retention data as modeling tools for biological distribution: Application to some oxime-type acetylcholinesterase reactivators

Author keywords

Chromatographic retention data; Descriptor correlation; Extrapolated retention; Hydrophobicity hydrophilicity descriptors; Modeling of biological partition

Indexed keywords

1 (4 CARBAMOYLPYRIDINIO) 1' (2 HYDROXYIMINOMETHYLPYRIDINIO)DIMETHYL ETHER; 1 [2,4 BIS(HYDROXYIMINOMETHYL)PYRIDINIO] 1' (4 CARBAMOYLPYRIDINIO)DIMETHYL ETHER DIIODIDE; 1 METHYL 3 (3 OXO 1 AZA BICYCLO[2.2.2]OCTANE 1 YLMETHYOXYMETHYL) 1H IMIDAZOLE 2 CARBALDEHYDE OXIME; 2 (HYDROXYIMINOMETHYL) 1,3 DIMETHYL 3H IMIDAZOL 1 IUM; CHOLINESTERASE INHIBITOR; CHOLINESTERASE REACTIVATOR; DIMETHYL CARBAMIC ACID 1 [2 (HYDROXYIMINOMETHYL) 3 METHYL 3H IMIDAZOL 1 YLMETHOXYMETHYL] 1 AZA BICYCLO[2.2.2]OCTANE 3 YL ESTER; ESTER DERIVATIVE; GLYCOPROTEIN; OBIDOXIME; ORGANIC SOLVENT; ORGANOPHOSPHORUS COMPOUND; OXIME; PRALIDOXIME; PYRIDINIUM DERIVATIVE; PYRIDOSTIGMINE; SODIUM CHLORIDE; UNCLASSIFIED DRUG; ACETYLCHOLINESTERASE;

EID: 77950371053     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.02.004     Document Type: Article
Times cited : (24)

References (40)
  • 2
    • 0036844787 scopus 로고    scopus 로고
    • Predicting blood-brain barrier partitioning of organic molecules using membrane interaction QSAR analysis
    • Iyer M., Mishra R., Han Y., Hopfinger A.J. Predicting blood-brain barrier partitioning of organic molecules using membrane interaction QSAR analysis. Pharm. Res. 2002, 19:1611-1621.
    • (2002) Pharm. Res. , vol.19 , pp. 1611-1621
    • Iyer, M.1    Mishra, R.2    Han, Y.3    Hopfinger, A.J.4
  • 3
    • 0031048588 scopus 로고    scopus 로고
    • On the partition of ampholytes: application to blood-brain distribution
    • Abraham M.H., Takacs-Novak K., Mitchell R.C. On the partition of ampholytes: application to blood-brain distribution. J. Pharm. Sci. 1997, 86:310-315.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 310-315
    • Abraham, M.H.1    Takacs-Novak, K.2    Mitchell, R.C.3
  • 4
    • 1642384018 scopus 로고    scopus 로고
    • The factors that influence permeation across the blood-brain barrier
    • Abraham M.H. The factors that influence permeation across the blood-brain barrier. Eur. J. Med. Chem. 2004, 39:235-240.
    • (2004) Eur. J. Med. Chem. , vol.39 , pp. 235-240
    • Abraham, M.H.1
  • 5
    • 25844495011 scopus 로고    scopus 로고
    • Medicinal chemical properties of successful central nervous system drugs
    • Pajouhesh H., Lenz G.R. Medicinal chemical properties of successful central nervous system drugs. J. Am. Soc. Exp. Neurother. 2005, 2:541-553.
    • (2005) J. Am. Soc. Exp. Neurother. , vol.2 , pp. 541-553
    • Pajouhesh, H.1    Lenz, G.R.2
  • 6
    • 52949094246 scopus 로고    scopus 로고
    • Predicting blood-brain barrier penetration from molecular weight and number of polar atoms
    • Fu X.C., Wang G.P., Shan H.L., Liang W.Q., Gao J.Q. Predicting blood-brain barrier penetration from molecular weight and number of polar atoms. Eur. J. Pharm. Biopharm. 2008, 70:462-466.
    • (2008) Eur. J. Pharm. Biopharm. , vol.70 , pp. 462-466
    • Fu, X.C.1    Wang, G.P.2    Shan, H.L.3    Liang, W.Q.4    Gao, J.Q.5
  • 7
    • 0032714220 scopus 로고    scopus 로고
    • Polar molecular surface as a dominating determinant for oral adsorption and brain penetration of drugs
    • Kelder J., Grootenhuis P.D.J., Bayada D.M., Delbressine L.P.C., Ploemen J.P. Polar molecular surface as a dominating determinant for oral adsorption and brain penetration of drugs. Pharm. Res. 1999, 16:1514-1519.
    • (1999) Pharm. Res. , vol.16 , pp. 1514-1519
    • Kelder, J.1    Grootenhuis, P.D.J.2    Bayada, D.M.3    Delbressine, L.P.C.4    Ploemen, J.P.5
  • 8
    • 0031695039 scopus 로고    scopus 로고
    • Blood brain barrier permeation: molecular parameters governing passive diffusion
    • Fischer H., Gottschlich R., Seelig A. Blood brain barrier permeation: molecular parameters governing passive diffusion. J. Membr. Biol. 1998, 165:201-211.
    • (1998) J. Membr. Biol. , vol.165 , pp. 201-211
    • Fischer, H.1    Gottschlich, R.2    Seelig, A.3
  • 9
    • 0035950120 scopus 로고    scopus 로고
    • Physicochemical determinants of passive membrane permeability: role of solute hydrogen bonding potential and volume
    • Goodwin J.T., Couradi R.A., Ho N.F.H., Burton P.S. Physicochemical determinants of passive membrane permeability: role of solute hydrogen bonding potential and volume. J. Med. Chem. 2001, 44:3721-3729.
    • (2001) J. Med. Chem. , vol.44 , pp. 3721-3729
    • Goodwin, J.T.1    Couradi, R.A.2    Ho, N.F.H.3    Burton, P.S.4
  • 11
    • 0022272070 scopus 로고
    • Partitioning and lipophilicity in quantitative structure-activity relationships
    • Dearden J.C. Partitioning and lipophilicity in quantitative structure-activity relationships. Environ. Health Perspect. 1985, 61:203-228.
    • (1985) Environ. Health Perspect. , vol.61 , pp. 203-228
    • Dearden, J.C.1
  • 12
    • 14744281423 scopus 로고    scopus 로고
    • Novel hydrophobicity ruler approach for determining the octanol/water partition coefficients of very hydrophobic compounds via their polymer/solvent solution distribution coefficients
    • Kong X.Q., Shea D., Gebreyes W.A., Xia X.R. Novel hydrophobicity ruler approach for determining the octanol/water partition coefficients of very hydrophobic compounds via their polymer/solvent solution distribution coefficients. Anal. Chem. 2005, 77:1275-1281.
    • (2005) Anal. Chem. , vol.77 , pp. 1275-1281
    • Kong, X.Q.1    Shea, D.2    Gebreyes, W.A.3    Xia, X.R.4
  • 13
    • 0034131971 scopus 로고    scopus 로고
    • Absorption of hydrophobic compounds into poly(dimethylsiloxane) coating of solid phase microextraction fibers: high partition coefficients and fluorescence microscopy images
    • Mayer P., Vaes W.H.J., Hermens J.L.M. Absorption of hydrophobic compounds into poly(dimethylsiloxane) coating of solid phase microextraction fibers: high partition coefficients and fluorescence microscopy images. Anal. Chem. 2000, 72:459-464.
    • (2000) Anal. Chem. , vol.72 , pp. 459-464
    • Mayer, P.1    Vaes, W.H.J.2    Hermens, J.L.M.3
  • 14
    • 0038777277 scopus 로고    scopus 로고
    • Solid Phase microextraction fibre-water distribution constants of more hydrophobic organic compounds and their correlation with octanol-water partition coefficients
    • Paschke A., Popp P. Solid Phase microextraction fibre-water distribution constants of more hydrophobic organic compounds and their correlation with octanol-water partition coefficients. J. Chromatogr. A 2003, 99:35-42.
    • (2003) J. Chromatogr. A , vol.99 , pp. 35-42
    • Paschke, A.1    Popp, P.2
  • 15
    • 0000873099 scopus 로고    scopus 로고
    • Solid phase microextraction as a method for estimating the octanol-water partition coefficient
    • Dean J.R., Tomlinson W.R., Makovskaya V., Cumming R., Hetheridge M., Comber M. Solid phase microextraction as a method for estimating the octanol-water partition coefficient. Anal. Chem. 1996, 68:130-133.
    • (1996) Anal. Chem. , vol.68 , pp. 130-133
    • Dean, J.R.1    Tomlinson, W.R.2    Makovskaya, V.3    Cumming, R.4    Hetheridge, M.5    Comber, M.6
  • 16
    • 0034238081 scopus 로고    scopus 로고
    • Determination of distribution coefficients of priority polycyclic aromatic hydrocarbons using solid phase microextraction
    • Dong R., Chang S. Determination of distribution coefficients of priority polycyclic aromatic hydrocarbons using solid phase microextraction. Anal. Chem. 2000, 72:3647-3652.
    • (2000) Anal. Chem. , vol.72 , pp. 3647-3652
    • Dong, R.1    Chang, S.2
  • 17
    • 33846955444 scopus 로고    scopus 로고
    • A high-throughput method for lipophilicity measurement
    • Chen Z., Weber S.G. A high-throughput method for lipophilicity measurement. Anal. Chem. 2007, 79:1043-1049.
    • (2007) Anal. Chem. , vol.79 , pp. 1043-1049
    • Chen, Z.1    Weber, S.G.2
  • 18
    • 2342627370 scopus 로고    scopus 로고
    • Determination of liquid-liquid partition coefficients by separation methods
    • Berthod A., Carda-Brosch S. Determination of liquid-liquid partition coefficients by separation methods. J. Chromatogr. A 2004, 1037:3-14.
    • (2004) J. Chromatogr. A , vol.1037 , pp. 3-14
    • Berthod, A.1    Carda-Brosch, S.2
  • 19
    • 0029947489 scopus 로고    scopus 로고
    • Methods for determiing n-octanol/water partition constants
    • Danielsson L.G., Zhang Y.H. Methods for determiing n-octanol/water partition constants. Trends Anal. Chem. 1996, 15:188-196.
    • (1996) Trends Anal. Chem. , vol.15 , pp. 188-196
    • Danielsson, L.G.1    Zhang, Y.H.2
  • 20
    • 0242663963 scopus 로고    scopus 로고
    • Separation methods for estimating octanol-water partition coefficients
    • Poole S.K., Poole C.F. Separation methods for estimating octanol-water partition coefficients. J. Chromatogr. B 2003, 797:3-19.
    • (2003) J. Chromatogr. B , vol.797 , pp. 3-19
    • Poole, S.K.1    Poole, C.F.2
  • 21
    • 2342635206 scopus 로고    scopus 로고
    • Application of high performance liquid chromatography based measurements of lipophilicity to model biological distribution
    • Valkó K. Application of high performance liquid chromatography based measurements of lipophilicity to model biological distribution. J. Chromatogr. A 2004, 1037:299-310.
    • (2004) J. Chromatogr. A , vol.1037 , pp. 299-310
    • Valkó, K.1
  • 22
    • 0000607945 scopus 로고    scopus 로고
    • Chromatographic hydrophobicity index by fast-gradient RP-HPLC: a high throughput alternative to logP/logD
    • Valkó K., Bevan C., Reynolds D. Chromatographic hydrophobicity index by fast-gradient RP-HPLC: a high throughput alternative to logP/logD. Anal. Chem. 1997, 69:2022-2029.
    • (1997) Anal. Chem. , vol.69 , pp. 2022-2029
    • Valkó, K.1    Bevan, C.2    Reynolds, D.3
  • 24
    • 77950369105 scopus 로고    scopus 로고
    • Prediction of the hydrophilic character of organic compounds (as molecular descriptor) from chromatographic retention data under HILIC partition mechanism
    • Voicu A.V., Medvedovici A., David V. Prediction of the hydrophilic character of organic compounds (as molecular descriptor) from chromatographic retention data under HILIC partition mechanism. Ther. Pharmacol. Clin. Toxicol 2009, 13:27-28.
    • (2009) Ther. Pharmacol. Clin. Toxicol , vol.13 , pp. 27-28
    • Voicu, A.V.1    Medvedovici, A.2    David, V.3
  • 25
    • 0037102534 scopus 로고    scopus 로고
    • Molecular structure, conformational analysis and charge distribution of pralidoxime: ab initio and DFT studies
    • Castro A.T., Figueroa-Villar J.D. Molecular structure, conformational analysis and charge distribution of pralidoxime: ab initio and DFT studies. Int. J. Quantum Chem. 2002, 89:135-146.
    • (2002) Int. J. Quantum Chem. , vol.89 , pp. 135-146
    • Castro, A.T.1    Figueroa-Villar, J.D.2
  • 27
    • 77950368360 scopus 로고    scopus 로고
    • Some oximes PK/PD correlations and therapeutic consequences
    • Voicu A.V. Some oximes PK/PD correlations and therapeutic consequences. Ther. Pharmacol. Clin. Toxicol 2009, 13:23-24.
    • (2009) Ther. Pharmacol. Clin. Toxicol , vol.13 , pp. 23-24
    • Voicu, A.V.1
  • 28
    • 42449115631 scopus 로고    scopus 로고
    • RP-HPLC determination of the lipophilicity of bispyridinium reactivators of acetylcholinesterase bearing a but-2-ene connecting linker
    • Musilek K., Jampilek J., Dohnal J., Jun D., Gunn-Moore F., Dolezal M., Kuca K. RP-HPLC determination of the lipophilicity of bispyridinium reactivators of acetylcholinesterase bearing a but-2-ene connecting linker. Anal. Bioanal. Chem. 2008, 391:367-372.
    • (2008) Anal. Bioanal. Chem. , vol.391 , pp. 367-372
    • Musilek, K.1    Jampilek, J.2    Dohnal, J.3    Jun, D.4    Gunn-Moore, F.5    Dolezal, M.6    Kuca, K.7
  • 29
    • 41649096835 scopus 로고    scopus 로고
    • Evaluation of potency of known oximes (pralidoxime, trimedoxime, HI-6, methoxime, obidoxime) to in-vitro reactivate acetylcholinesterase inhibited by pesticides (chlorpyrifos and methylchlorpyrifos) and nerve agent (Russian VX)
    • Musilek K., Kuca K., Jun D. Evaluation of potency of known oximes (pralidoxime, trimedoxime, HI-6, methoxime, obidoxime) to in-vitro reactivate acetylcholinesterase inhibited by pesticides (chlorpyrifos and methylchlorpyrifos) and nerve agent (Russian VX). Acta Med. 2007, 50:203-206.
    • (2007) Acta Med. , vol.50 , pp. 203-206
    • Musilek, K.1    Kuca, K.2    Jun, D.3
  • 31
    • 33745976170 scopus 로고    scopus 로고
    • High-performance liquid chromatographic determination of the plasma concentration of K-27, a novel oxime-type cholinesterase reactivator
    • Tekes K., Hasan M.Y., Sheen R., Kuca K., Petroianu G., Ludányi K., Kalász H. High-performance liquid chromatographic determination of the plasma concentration of K-27, a novel oxime-type cholinesterase reactivator. J. Chromatogr. A 2006, 1122:84-87.
    • (2006) J. Chromatogr. A , vol.1122 , pp. 84-87
    • Tekes, K.1    Hasan, M.Y.2    Sheen, R.3    Kuca, K.4    Petroianu, G.5    Ludányi, K.6    Kalász, H.7
  • 35
    • 12044255753 scopus 로고
    • Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes
    • Abraham M.H. Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes. Chem. Soc. Rev. 1993, 22:73-84.
    • (1993) Chem. Soc. Rev. , vol.22 , pp. 73-84
    • Abraham, M.H.1
  • 37
    • 0029007493 scopus 로고
    • Relationships between binding of benzodiazepines to alpha-1-acid glycoprotein and human serum albumin and their retention on the protein and octadecylsilane columns
    • Sadlej-Sosnowska N. Relationships between binding of benzodiazepines to alpha-1-acid glycoprotein and human serum albumin and their retention on the protein and octadecylsilane columns. Biomed. Chromatogr. 1995, 9:150-151.
    • (1995) Biomed. Chromatogr. , vol.9 , pp. 150-151
    • Sadlej-Sosnowska, N.1
  • 38
    • 0035975898 scopus 로고    scopus 로고
    • Quantitative structure/retention relationships in affinity chromatography
    • Backek T., Kaliszan R. Quantitative structure/retention relationships in affinity chromatography. J. Biochem. Biophys. Methods 2001, 49:83-98.
    • (2001) J. Biochem. Biophys. Methods , vol.49 , pp. 83-98
    • Backek, T.1    Kaliszan, R.2
  • 39
    • 34547495638 scopus 로고    scopus 로고
    • QSRR: quantitative structure-(chromatographic) retention relationships
    • Kaliszan R. QSRR: quantitative structure-(chromatographic) retention relationships. Chem. Rev. 2007, 107:3212-3246.
    • (2007) Chem. Rev. , vol.107 , pp. 3212-3246
    • Kaliszan, R.1
  • 40
    • 33947122617 scopus 로고    scopus 로고
    • Structure-retention correlation in liquid chromatography for pharmaceutical applications
    • David V., Medvedovici A. Structure-retention correlation in liquid chromatography for pharmaceutical applications. J. Liq. Chromatogr. Rel. Technol. 2007, 30:761-789.
    • (2007) J. Liq. Chromatogr. Rel. Technol. , vol.30 , pp. 761-789
    • David, V.1    Medvedovici, A.2


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