The Thermodynamic Dissociation Constants of Azathioprine by the Nonlinear Regression and Factor Analysis of Multiwavelength Spectrophotometric pH-Titration Data

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References

[1] “Azathioprine,” Encyclopedia Britannica, 2009. http://www. britan-nica.com/EBchecked/topic/46740/azathioprine

[2]
G. E. Cheney, H. Freiser and Q. Fernando, “Metal Com-plexes of Purine and some of its Derivatives,” Journal of the American Chemical Society, Vol. 81, No. 11, 1959, pp. 2611-2615.

[3]
D. E. Duggan and E. Titus, “6-Chloropurine and 6- Chlorouric Acid as Substrates and Inhibitors of Purine- Oxidizing Enzymes,” Journal of Biological Chemistry, Vol. 234, No. 8, 1959, pp. 2100-2104.

[4]
J. D. Davidson, “Studies on the Mechanism of Action of 6-Mercaptopurine in Sensitive and Resistant L1210 Leu-kemia in Vitro,” Cancer Research, Vol. 20, No. 2, 1960, pp. 225-232.

[5]
U. Kela and R. Vijayvargiya, “Studies on the Mechanism of Action of 6-Mercaptopurine,” Biochemistry Journal, Vol. 193, No. 3, 1981, pp. 799-803.

[6]
E. Mavioglu, S. Arzik and A. S. Celebi: Potentric Deter-mination of the Stability Constants of Ni(II), Co(II), Cu(II) and Zn(II) Complexes of Hypoxanthine at Physiological Conditions. JFS 27 (2004), 1-19

[7]
M. J. Robins and G. L. Basom, “Nucleic Acid Related Compounds. 8. Direct Conversion of 2’-Deoxyinosine to 6-Chloropurine 2’-Deoxyriboside and Selected 6-Substitued Deoxynucleosides and their Evaluation as Substrates of Adenosine Deaminase,” Canadian Journal of Chemistry, Vol. 51, No. 19, 1973, pp. 3161-3169

[8]
O. Bibi, J. Schwartz, Y. Eilam, E. Shohami and Z. I. Ca-bantchik, “Nucleoside Transport in Mammalian Cell. IV. Organomercurials and Organomercurial-Mercaptonucleo- side Complexes as Probes for Nucleoside Transport Sys-tems in Hamster Cells,” Journal of Membrane Biology, Vol. 39, No. 2-3, 1978, pp. 159-183

[9]
M. Meloun, J. Čapek, P. Mikšík and R. G. Brereton, “Critical of Methods Predicting the Number of Compo-nents in Spectroscopic Data,” Analytica Chimica Acta, Vol. 423, No. 1, 2000, pp. 51-68.

[10]
M. Meloun and M. Pluhařová, “Thermodynamic Dissoci-ation Constants of Codeine, Ethylmorphine and Homa-tropine by Regression Analysis of Potentiometric Titration Data, Analytica Chimica Acta, Vol. 416, No. 1, 2000 pp. 55-68.

[11]
M. Meloun and P. Černohorský, “Thermodynamic Dis-sociation Constants of Isocaine, Physostigmine and Pilo-carpine by Regression Analysis of Potentiometric Data,” Talanta, Vol. 52, No. 5, 2000, pp. 931-945.

[12]
M. Meloun, D. Burkoňová, T. Syrový and A. Vrána: The Thermodynamic Dissociation Constants of Silychristin, Silybin, Silydianin and Mycophenolate by the Regression Analysis of Spectrophotometric Data, Analytica Chimica Acta, Vol. 486, No. 1, 2003, pp. 125-141.

[13]
M. Meloun, T. Syrový and A. Vrána, “Determination of the Number of Light-Absorbing Species in the Protonation Equilibria of Selected Drugs,” Analytica Chimica Acta, Vol. 489, No. 2, 2003, pp. 137-151.

[14]
M. Meloun, T. Syrový and A. Vrána, “The Thermody-namic Dissociation Constants of Ambroxol, Antazoline, Naphazoline, Oxymetazoline and Ranitidine by the Re-gression Analysis of Spectrophotometric Data,” Talanta, Vol. 62, No. 3, 2004, pp. 511-522.

[15]
M. Meloun, T. Syrový and A. Vrána, “The Thermody-namic Dissociation Constants of Losartan, Paracetamol, Phenylephrine and Quinine by the Regression Analysis of Spectrophotometric Data,” Analytica Chimica Acta, Vol. 533, No. 1, 2005, pp. 97-110.

[16]
M. Meloun, T. Syrový and A. Vrána, “The Thermodynamic Dissociation Constants of Haemanthamine, Lisuride, Metergoline and Nicergoline by the Regression Analysis of Spectrophotometric Data, Analytica Chimica Acta, Vol. 543, No. 1-2, 2005, pp. 254-266.

[17]
M. Meloun, M. Javůrek and J. Militký, “Computer Esti-mation of Dissociation Constants. Part V: Regression Analysis of Extended Debye-Hückel Law,” Microchimica Acta, Vol. 109, No. 2-3, 1992, pp. 221-231.

[18]
M. Meloun, J. Havel and E. Högfeldt, “Computation of Solution Equilibria,” Ellis Horwood, Chichester, 1988.

[19]
M. Meloun and J. Havel, “Computation of Solution equi-libria, Part 1: Spectrophotometry,” Folia Facultatis Scientarum Naturalium Universitatis Purkynianae, Brno 1984.

[20]
M. Meloun and J. Havel, “Computation of Solution equi-libria, Part 2: Potentiometry,” Folia Facultatis Scientarum Naturalium Universitatis Purkynianae, Brno 1985.

[21]
M. Meloun, S. Bordovská, T. Syrový and A. Vrána, “Tu-torial on Chemical Model Building and Testing to Spec-troscopic Data with Least-Squares Regression,” Analytica Chimica Acta, Vol. 580, No. 1, 2006, pp. 107-121.

[22]
M. Meloun, S. Bordovská and T. Syrový, “A Novel Computational Strategy for the pKa Estimation of Drugs by Nonlinear Regression of Multiwavelength Spectro-photometric pH-Titration Data Exhibiting Small Changes,” Journal of Physical Organic Chemistry, Vol. 20, 2007, pp. 690-701.

[23]
M. Meloun, S. Bordovská and L. Galla, “The Thermody-namic Dissociation Constants of Four Non-Steroidal An-ti-Inflammatory Drugs by the Least-Squares Nonlinear Regression of Multiwavelength Spectrophotometric pH- Titration Data,” Journal of the Pharmaceutical and Bio-medical Analysis, Vol. 45, No. 4, 2007, pp. 552-564.

[24]
M. Meloun, S. Bordovská, Benchmarking and Validating Algorithms that Estimate pKa Values of Drugs Based on their Molecular Structures,” Analytical and Bioanalytical Chemistry, Vol. 389, No. 4, 2007, pp. 1267-1281.

[25]
M. Meloun, S. Bordovská and A. Vrána, “The Thermo-dynamic Dissociation Constants of the Anticancer Drugs Camptothecine, 7-Ethyl-10-Hydroxycamptothecine, 10- Hydroxycamptothecine, and 7-Ethylcamptothecine by the Least-Squares Nonlinear Regression of Multiwavelength Spectrophotometric pH-Titration Data, Analytica Chimica Acta, Vol. 584, No. 2, 2007, pp. 419-432.

[26]
M. Meloun, T. Syrový, S. Bordovská and A. Vrána, Re-liability and Uncertainty in the Estimation of pKa by the Least Squares Nonlinear Regression Analysis of Multi-wavelength Spectrophotometric pH Titration Data,” Ana-lytical and Bioanalytical Chemistry, Vol. 387, No. 3, 2007, pp. 941-955.

[27]
L. G. Sillén and B. Warnqvist, “Equilibrium Constants and Model Testing from Spectrophotometric Data, Using LETAGROP,” Acta Chemica Scandinavia, Vol. 22, 1968, pp. 3032-3034.

[28]
D. J. Leggett, “Computational Methods for the Determi-nation of Formation Constants,” In: D. J. Leggett, Ed., Plenum Press, New York, 1985.

[29]
J. Havel and M. Meloun, “Computational Methods for the Determination of Formation Constants,” In: D. J. Leggett, Ed., Plenum Press, New York, 1985.

[30]
M. Meloun, M. Javůrek and J. Havel, “Multiparametric curve Fitting-X. A Structural Classification of Program for Analysing Multicomponent Spectra and their Use in Equilibrium-Model Determination,” Talanta, Vol. 33, No. 6, 1986, pp. 513-524.

[31]
D. J. Leggett and W. A. E. McBryde, “General Computer Program for the Computation of Stability Constants from Absorbance Data,” Analytical Chemistry, Vol. 47, No. 7, 1975, pp. 1065-1070.

[32]
D. J. Leggett, “Numerical Analysis of Multicomponent Spectra,” Analytical Chemistry, Vol. 49, No. 2, 1977, pp. 276- 281.

[33]
D. J. Leggett, S. L. Kelly, L. R. Shiue, Y. T. Wu, D. Chang and K. M. Kadish, “A Computational Approach to the Spectrophotometric Determination of Stability Con-stants—2: Application to Metalloporphyrin Axial Ligand Interactions in Non-Aqueous Solvents,” Talanta, Vol. 30, No. 8, 1983, pp. 579-586.

[34]
J. J. Kankare, “Computation of Equilibrium Constants for Multicomponent Systems from Spectrophoto-Metric Da-ta,” Analytical Chemistry, Vol. 42, No. 12, 1970, pp. 1322-1326.

[35]
P. Gans, A. Sabatini and A. Vacca, “Investigation of Equilibria in Solution. Determination of Equilibrium Constants with the HYPERQUAD Suite of Programs,” Talanta, Vol. 43, No. 10, 1996, pp. 1739-1753.

[36]
H. Gampp, M. Maeder, C. J. Mayer and A. Zuberbuhler, “Calculation of Equilibrium Constants from Multiwave-length Spectroscopic Data—I: Mathematical Considera-tions, Talanta, Vol. 32, No. 2, 1985, pp. 95-101.

[37]
H. Gampp., M. Maeder, C. J. Meyer and A. Zuberbühler, Calculation of Equilibrium Constants from Multiwave-length Spectroscopic Data—II: Specfit: Two User-Friendly Programs in Basic and Standard Fortran 77,” Talanta, Vol. 32, No. 4, 1985, pp. 251-264.

[38]
H. Gampp., M. Maeder, C. J. Meyer and A. Zuberbühler, “Calculation of Equilibrium Constants from Multiwave-length Spectroscopic Data—III: Model-Free Analysis of Spectrophotometric and ESR Titrations,” Talanta, Vol. 32, No. 12, 1985, pp. 1133-1139.

[39]
H. Gampp., M. Maeder, C. J. Meyer and A. Zuberbühler, “Calculation of Equilibrium Constants from Multiwave-length Spectroscopic Data—IV: Model-Free Least-Squares Refinement by Use of Evolving Factor Analysis, Talanta, Vol. 33, No. 12, 1986, pp. 943-951.

[40]
K. Y. Tam and K. Takács-Novák, “Multi-Wavelength Spectrophotometric Determination of Acid Dissociation Constants: A Validation Study,” Analytica Chimica Acta, Vol. 434, No. 1, 2001, pp. 157-167.

[41]
SPECFIT/32, Spectrum Software Associates, Marlbo-rough, 2004. http://www.bio-logic.info/rapid-kinetics/specfit. html

[42]
T. H. Scheuermann, C. Keeler and M. E. Hodson, “Con-sequences of Binding an S-Adenosylmethionine Analogue on the Structure and Dynamics of the Thiopurine Methyltransferase Protein Backbone, Biochemistry, Vol. 43, No. 38, 2004, pp. 12198-12209.

[43]
Pallas. http://compudrug.com/show.php?id=90. http:// compudrug.com/show.php?id=36.

[44]
M. Meloun, J. Militký and M. Forina, Chemometrics for Analytical Chemistry—Vol. 1. PC-Aided Statistical Data Analysis, Ellis Horwood, Chichester, 1992.

[45]
M. Meloun, J. Militký and M. Forina, Chemometrics for Analytical Chemistry—Vol. 2. PC-Aided Regression and Related Methods, Ellis Horwood, Chichester, 1994.

[46]
ORIGIN, OriginLab Corporation, Northampton.

[47]
M. Meloun, T. Syrový and A. Vrána, “Determination of the Number of Light-Absorbing Species in the Protonation Equilibria of Selected Drugs,” Analytica Chimica Acta, Vol. 489, No. 2, 2003, pp. 137-151.

[48]
S-PLUS. http://www.insightful.com/products/splus

[49]
ADSTAT, ADSTAT 1.25, 2.0, 3.0 (Windows 95), Trilo-Byte Statistical Software Ltd., Pardubice.