메뉴 건너뛰기




Volumn 94, Issue , 2014, Pages 180-187

The simultaneous determination of hydrophobicity and dissociation constant by liquid chromatography-mass spectrometry

Author keywords

Acidity; Gradient RP HPLC; Hydrophobicity; PH organic modifier; Throughput analysis

Indexed keywords

AMINOPHENAZONE; AMITRIPTYLINE; AMMONIUM ACETATE; AMMONIUM FORMATE; BUFFER; CHLORPHENIRAMINE; CIMETIDINE; CLONIDINE; COCAINE; DICLOFENAC; DIPHENHYDRAMINE; IMIPRAMINE; LIDOCAINE; METOCLOPRAMIDE; METOPROLOL; METRONIDAZOLE; NICOTINE; NORTRIPTYLINE; PARACETAMOL; PHENOBARBITAL; PHENYLBUTAZONE; PINDOLOL; PROCAINAMIDE; PROCAINE; PROMETHAZINE; SALICYLIC ACID; TETRACAINE; THEOPHYLLINE; UNINDEXED DRUG; WARFARIN;

EID: 84896807902     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2014.01.038     Document Type: Article
Times cited : (27)

References (43)
  • 1
    • 79955599163 scopus 로고    scopus 로고
    • Lipophilicity and its relationship with passive drug permeation
    • Liu X.L., Testa B., Fahr A. Lipophilicity and its relationship with passive drug permeation. Pharmaceut. Res. 2011, 28:962-977.
    • (2011) Pharmaceut. Res. , vol.28 , pp. 962-977
    • Liu, X.L.1    Testa, B.2    Fahr, A.3
  • 2
    • 80052415183 scopus 로고    scopus 로고
    • Gradient reversed-phase high-performance chromatography of ionogenic analytes
    • Kaliszan R., Wiczling P. Gradient reversed-phase high-performance chromatography of ionogenic analytes. Trend. Anal. Chem. 2011, 30:1372-1381.
    • (2011) Trend. Anal. Chem. , vol.30 , pp. 1372-1381
    • Kaliszan, R.1    Wiczling, P.2
  • 3
    • 0036809320 scopus 로고    scopus 로고
    • Physicochemical profiling in drug research: a brief survey of the state-of-the-art of experimental techniques
    • Avdeef A., Testa B. Physicochemical profiling in drug research: a brief survey of the state-of-the-art of experimental techniques. Cell Mol. Life Sci. 2002, 59:1681-1689.
    • (2002) Cell Mol. Life Sci. , vol.59 , pp. 1681-1689
    • Avdeef, A.1    Testa, B.2
  • 4
    • 0037278031 scopus 로고    scopus 로고
    • Chromatographic retention parameters in medicinal chemistry and molecular pharmacology
    • Nasal A., Siluk D., Kaliszan R. Chromatographic retention parameters in medicinal chemistry and molecular pharmacology. Curr. Med. Chem. 2003, 10:381-426.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 381-426
    • Nasal, A.1    Siluk, D.2    Kaliszan, R.3
  • 5
    • 34247556082 scopus 로고    scopus 로고
    • Mechanistic approaches to volume of distribution predictions: understanding the processes
    • Rodgers T., Rowland M. Mechanistic approaches to volume of distribution predictions: understanding the processes. Pharmaceut. Res. 2007, 24:918-933.
    • (2007) Pharmaceut. Res. , vol.24 , pp. 918-933
    • Rodgers, T.1    Rowland, M.2
  • 7
    • 35948978100 scopus 로고    scopus 로고
    • Current state of the art in HPLC methodology for lipophilicity assessment of basic drugs. A review
    • Giaginis C., Tsantili-Kakoulidou A. Current state of the art in HPLC methodology for lipophilicity assessment of basic drugs. A review. J. Liq. Chromatogr. Relat. Technol. 2008, 31:79-96.
    • (2008) J. Liq. Chromatogr. Relat. Technol. , vol.31 , pp. 79-96
    • Giaginis, C.1    Tsantili-Kakoulidou, A.2
  • 8
    • 0000607945 scopus 로고    scopus 로고
    • Chromatographic hydrophobicity index by fast-gradient RP HPLC: a high-throughput alternative to logP logD
    • Valko 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
    • Valko, K.1    Bevan, C.2    Reynolds, D.3
  • 9
    • 47349111077 scopus 로고    scopus 로고
    • LogD: lipophilicity for ionisable compounds
    • Kah M., Brown C.D. LogD: lipophilicity for ionisable compounds. Chemosphere 2008, 72:1401-1408.
    • (2008) Chemosphere , vol.72 , pp. 1401-1408
    • Kah, M.1    Brown, C.D.2
  • 11
    • 30044448754 scopus 로고    scopus 로고
    • Simultaneous determination of pKa and lipophilicity by gradient RP HPLC
    • Wiczling P., Kawczak P., Nasal A., Kaliszan R. Simultaneous determination of pKa and lipophilicity by gradient RP HPLC. Anal. Chem. 2006, 78:239-249.
    • (2006) Anal. Chem. , vol.78 , pp. 239-249
    • Wiczling, P.1    Kawczak, P.2    Nasal, A.3    Kaliszan, R.4
  • 14
    • 26944468690 scopus 로고    scopus 로고
    • Searching for robust HPLC methods - Csaba Horvath and the solvophobic theory
    • Molnar I. Searching for robust HPLC methods - Csaba Horvath and the solvophobic theory. Chromatographia 2005, 62:S7-S17.
    • (2005) Chromatographia , vol.62
    • Molnar, I.1
  • 15
    • 9644295485 scopus 로고
    • Solvophobic interactions in liquid-chromatography with nonpolar stationary phases
    • Horvath C., Melander W., Molnar I. Solvophobic interactions in liquid-chromatography with nonpolar stationary phases. J. Chromatogr. 1976, 125:129-156.
    • (1976) J. Chromatogr. , vol.125 , pp. 129-156
    • Horvath, C.1    Melander, W.2    Molnar, I.3
  • 16
    • 84872424550 scopus 로고    scopus 로고
    • The contribution of the hydrogen bond acidity on the lipophilicity of drugs estimated from chromatographic measurements
    • Pallicer J.M., Pascual R., Port A., Roses M., Rafols C., Bosch E. The contribution of the hydrogen bond acidity on the lipophilicity of drugs estimated from chromatographic measurements. Eur. J. Pharm. Sci. 2013, 48:484-493.
    • (2013) Eur. J. Pharm. Sci. , vol.48 , pp. 484-493
    • Pallicer, J.M.1    Pascual, R.2    Port, A.3    Roses, M.4    Rafols, C.5    Bosch, E.6
  • 17
    • 0027982335 scopus 로고
    • Hydrogen-bonding. 32. An analysis of water-octanol and water-alkane partitioning and the delta-log-P parameter of seiler
    • Abraham M.H., Chadha H.S., Whiting G.S., Mitchell R.C. Hydrogen-bonding. 32. An analysis of water-octanol and water-alkane partitioning and the delta-log-P parameter of seiler. J. Pharm. Sci. 1994, 83:1085-1100.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1085-1100
    • Abraham, M.H.1    Chadha, H.S.2    Whiting, G.S.3    Mitchell, R.C.4
  • 18
    • 0035742979 scopus 로고    scopus 로고
    • Gradient HPLC in the determination of drug lipophilicity and acidity
    • Kaliszan R., Haber P., Baczek T., Siluk D. Gradient HPLC in the determination of drug lipophilicity and acidity. Pure Appl. Chem. 2001, 73:1465-1475.
    • (2001) Pure Appl. Chem. , vol.73 , pp. 1465-1475
    • Kaliszan, R.1    Haber, P.2    Baczek, T.3    Siluk, D.4
  • 19
    • 0037008235 scopus 로고    scopus 로고
    • Lipophilicity and pKa estimates from gradient high-performance liquid chromatography
    • Kaliszan R., Haber P., Baczek T., Siluk D., Valko K. Lipophilicity and pKa estimates from gradient high-performance liquid chromatography. J. Chromatogr. A 2002, 965:117-127.
    • (2002) J. Chromatogr. A , vol.965 , pp. 117-127
    • Kaliszan, R.1    Haber, P.2    Baczek, T.3    Siluk, D.4    Valko, K.5
  • 20
    • 9644280960 scopus 로고    scopus 로고
    • PH gradient high-performance liquid chromatography: theory and applications
    • Kaliszan R., Wiczling P., Markuszewski M.J. pH gradient high-performance liquid chromatography: theory and applications. J. Chromatogr. A 2004, 1060:165-175.
    • (2004) J. Chromatogr. A , vol.1060 , pp. 165-175
    • Kaliszan, R.1    Wiczling, P.2    Markuszewski, M.J.3
  • 22
    • 0033969755 scopus 로고    scopus 로고
    • Modelling retention in liquid chromatography as a function of solvent composition and pH of the mobile phase
    • Berges R., Sanz-Nebot V., Barbosa J. Modelling retention in liquid chromatography as a function of solvent composition and pH of the mobile phase. J. Chromatogr. A 2000, 869:27-39.
    • (2000) J. Chromatogr. A , vol.869 , pp. 27-39
    • Berges, R.1    Sanz-Nebot, V.2    Barbosa, J.3
  • 23
    • 0031666177 scopus 로고    scopus 로고
    • Determination of dissociation constants of polyprotic acids from chromatographic data
    • Hardcastle J.E., Jano I. Determination of dissociation constants of polyprotic acids from chromatographic data. J. Chromatogr. B 1998, 717:39-56.
    • (1998) J. Chromatogr. B , vol.717 , pp. 39-56
    • Hardcastle, J.E.1    Jano, I.2
  • 24
    • 0037144240 scopus 로고    scopus 로고
    • New equations describing the combined effect of pH and organic modifier concentration on the retention in reversed-phase liquid chromatography
    • Nikitas P., Pappa-Louisi A. New equations describing the combined effect of pH and organic modifier concentration on the retention in reversed-phase liquid chromatography. J. Chromatogr. A 2002, 971:47-60.
    • (2002) J. Chromatogr. A , vol.971 , pp. 47-60
    • Nikitas, P.1    Pappa-Louisi, A.2
  • 25
    • 59649103562 scopus 로고    scopus 로고
    • Retention models for isocratic and gradient elution in reversed-phase liquid chromatography
    • Nikitas P., Pappa-Louisi A. Retention models for isocratic and gradient elution in reversed-phase liquid chromatography. J. Chromatogr. A 2009, 1216:1737-1755.
    • (2009) J. Chromatogr. A , vol.1216 , pp. 1737-1755
    • Nikitas, P.1    Pappa-Louisi, A.2
  • 26
    • 43449127764 scopus 로고    scopus 로고
    • Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds II: benefits of the simultaneous optimisation
    • Pous-Torres S., Torres-Lapasio J.R., Baeza-Baeza J.J., Garcia-Alvarez-Coque M.C. Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds II: benefits of the simultaneous optimisation. J. Chromatogr. A 2008, 1193:117-128.
    • (2008) J. Chromatogr. A , vol.1193 , pp. 117-128
    • Pous-Torres, S.1    Torres-Lapasio, J.R.2    Baeza-Baeza, J.J.3    Garcia-Alvarez-Coque, M.C.4
  • 27
    • 84864612021 scopus 로고    scopus 로고
    • PH-gradient reversed-phase liquid chromatography of ionogenic analytes revisited
    • Nikitas P., Pappa-Louisi A., Zisi C. pH-gradient reversed-phase liquid chromatography of ionogenic analytes revisited. Anal. Chem. 2012, 84:6611-6618.
    • (2012) Anal. Chem. , vol.84 , pp. 6611-6618
    • Nikitas, P.1    Pappa-Louisi, A.2    Zisi, C.3
  • 28
    • 84878694715 scopus 로고    scopus 로고
    • Retention modeling in combined pH/organic solvent gradient reversed-phase HPLC
    • Zisi C., Fasoula S., Nikitas P., Pappa-Louisi A. Retention modeling in combined pH/organic solvent gradient reversed-phase HPLC. Analyst 2013, 138:3771-3777.
    • (2013) Analyst , vol.138 , pp. 3771-3777
    • Zisi, C.1    Fasoula, S.2    Nikitas, P.3    Pappa-Louisi, A.4
  • 29
    • 56549101330 scopus 로고    scopus 로고
    • The application of gradient reversed-phase high-performance liquid chromatography to the pK(a) and logk(w) determination of polyprotic analytes
    • Wiczling P., Waszczuk-Jankowska M., Markuszewski M.J., Kaliszan R. The application of gradient reversed-phase high-performance liquid chromatography to the pK(a) and logk(w) determination of polyprotic analytes. J. Chromatogr. A 2008, 1214:109-114.
    • (2008) J. Chromatogr. A , vol.1214 , pp. 109-114
    • Wiczling, P.1    Waszczuk-Jankowska, M.2    Markuszewski, M.J.3    Kaliszan, R.4
  • 30
    • 77952240601 scopus 로고    scopus 로고
    • Retention time and peak width in the combined pH/organic modifier gradient high performance liquid chromatography
    • Wiczling P., Kaliszan R. Retention time and peak width in the combined pH/organic modifier gradient high performance liquid chromatography. J. Chromatogr. A 2010, 1217:3375-3381.
    • (2010) J. Chromatogr. A , vol.1217 , pp. 3375-3381
    • Wiczling, P.1    Kaliszan, R.2
  • 31
    • 84861034420 scopus 로고    scopus 로고
    • A new pH/organic modifier gradient RP HPLC method for convenient determination of lipophilicity and acidity of drugs as applied to established imidazoline agents
    • Wiczling P., Nasal A., Kubik L., Kaliszan R. A new pH/organic modifier gradient RP HPLC method for convenient determination of lipophilicity and acidity of drugs as applied to established imidazoline agents. Eur. J. Pharm. Sci. 2012, 47:1-5.
    • (2012) Eur. J. Pharm. Sci. , vol.47 , pp. 1-5
    • Wiczling, P.1    Nasal, A.2    Kubik, L.3    Kaliszan, R.4
  • 32
    • 0000607945 scopus 로고    scopus 로고
    • Chromatographic hydrophobicity index by fast-gradient RP-HPLC: a high-throughput alternative to logP/logD
    • Valko K. 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
    • Valko, K.1
  • 33
    • 0000855358 scopus 로고    scopus 로고
    • Rapid gradient RP-HPLC method for lipophilicity determination: a solvation equation based comparison with isocratic methods
    • Du C.M., Valko K., Bevan C., Reynolds D., Abraham M.H. Rapid gradient RP-HPLC method for lipophilicity determination: a solvation equation based comparison with isocratic methods. Anal. Chem. 1998, 70:4228-4234.
    • (1998) Anal. Chem. , vol.70 , pp. 4228-4234
    • Du, C.M.1    Valko, K.2    Bevan, C.3    Reynolds, D.4    Abraham, M.H.5
  • 34
    • 29644431671 scopus 로고    scopus 로고
    • Medium throughput pKa determination of drugs and chemicals using an HPLC equipped with a DAD as a flow injection apparatus
    • Chiang P.C., Su C.C., Block K.M., Pretzer D.K. Medium throughput pKa determination of drugs and chemicals using an HPLC equipped with a DAD as a flow injection apparatus. J. Liq. Chromatogr. Relat. Technol. 2005, 28:3035-3043.
    • (2005) J. Liq. Chromatogr. Relat. Technol. , vol.28 , pp. 3035-3043
    • Chiang, P.C.1    Su, C.C.2    Block, K.M.3    Pretzer, D.K.4
  • 36
    • 66649084035 scopus 로고    scopus 로고
    • Retention of ionisable compounds on high-performance liquid chromatography XIX. pH variation in mobile phases containing formic acid, piperazine and Tris as buffering systems and methanol as organic modifier
    • Subirats X., Bosch E., Roses M. Retention of ionisable compounds on high-performance liquid chromatography XIX. pH variation in mobile phases containing formic acid, piperazine and Tris as buffering systems and methanol as organic modifier. J. Chromatogr. A 2009, 1216:5445-5448.
    • (2009) J. Chromatogr. A , vol.1216 , pp. 5445-5448
    • Subirats, X.1    Bosch, E.2    Roses, M.3
  • 37
    • 33845389529 scopus 로고    scopus 로고
    • Retention of ionisable compounds on high-performance liquid chromatography XVII. Estimation of the pH variation of aqueous buffers with the change of the methanol fraction of the mobile phase
    • Subirats X., Bosch E., Roses M. Retention of ionisable compounds on high-performance liquid chromatography XVII. Estimation of the pH variation of aqueous buffers with the change of the methanol fraction of the mobile phase. J. Chromatogr. A 2007, 1138:203-215.
    • (2007) J. Chromatogr. A , vol.1138 , pp. 203-215
    • Subirats, X.1    Bosch, E.2    Roses, M.3
  • 38
    • 2342459080 scopus 로고    scopus 로고
    • Determination of the pH of binary mobile phases for reversed-phase liquid chromatography
    • Roses M. Determination of the pH of binary mobile phases for reversed-phase liquid chromatography. J. Chromatogr. A 2004, 1037:283-298.
    • (2004) J. Chromatogr. A , vol.1037 , pp. 283-298
    • Roses, M.1
  • 39
    • 0037146784 scopus 로고    scopus 로고
    • Influence of mobile phase acid-base equilibria on the chromatographic behaviour of protolytic compounds
    • Roses M., Bosch E. Influence of mobile phase acid-base equilibria on the chromatographic behaviour of protolytic compounds. J. Chromatogr. A 2002, 982:1-30.
    • (2002) J. Chromatogr. A , vol.982 , pp. 1-30
    • Roses, M.1    Bosch, E.2
  • 40
    • 54349098960 scopus 로고    scopus 로고
    • Influence of pH on retention in linear organic modifier gradient RP HPLC
    • Wiczling P., Kaliszan R. Influence of pH on retention in linear organic modifier gradient RP HPLC. Anal. Chem. 2008, 80:7855-7861.
    • (2008) Anal. Chem. , vol.80 , pp. 7855-7861
    • Wiczling, P.1    Kaliszan, R.2
  • 41
    • 0035887259 scopus 로고    scopus 로고
    • Retention of ionizable compounds on HPLC. 8. Influence of mobile-phase pH change on the chromatographic retention of acids and bases during gradient elution
    • Canals I., Valko K., Bosch E., Hill A.P., Roses M. Retention of ionizable compounds on HPLC. 8. Influence of mobile-phase pH change on the chromatographic retention of acids and bases during gradient elution. Anal. Chem. 2001, 73:4937-4945.
    • (2001) Anal. Chem. , vol.73 , pp. 4937-4945
    • Canals, I.1    Valko, K.2    Bosch, E.3    Hill, A.P.4    Roses, M.5
  • 42
    • 0035468033 scopus 로고    scopus 로고
    • Physicochemical profiling (solubility, permeability and charge state)
    • Avdeef A. Physicochemical profiling (solubility, permeability and charge state). Curr. Top. Med. Chem. 2001, 1:277-351.
    • (2001) Curr. Top. Med. Chem. , vol.1 , pp. 277-351
    • Avdeef, A.1
  • 43
    • 0035800677 scopus 로고    scopus 로고
    • Dependence of reversed-phase retention of ionizable analytes on pH, concentration of organic solvent and silanol activity
    • Neue U.D., Phoebe C.H., Tran K., Cheng Y.F., Lu Z. Dependence of reversed-phase retention of ionizable analytes on pH, concentration of organic solvent and silanol activity. J. Chromatogr. A 2001, 925:49-67.
    • (2001) J. Chromatogr. A , vol.925 , pp. 49-67
    • Neue, U.D.1    Phoebe, C.H.2    Tran, K.3    Cheng, Y.F.4    Lu, Z.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.