Cytisine basicity, solvation, log P, and log D theoretical determination as tool for bioavailability prediction

Journal of Molecular Graphics and Modelling

Volumn 63, Issue , 2016, Pages 15-21

  Pieńko, Tomasz ^a,c   Grudzień, Monika ^a   Taciak, Przemysław Paweł ^a   Mazurek, Aleksander Paweł ^a,b  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

^b NATIONAL MEDICINES INSTITUTE   (Poland)

^c UNIVERSITY OF WARSAW   (Poland)

Author keywords

Acidic dissociation constant (pKa); Distribution coefficient (log D); Gibbs free energy of solvation; Partition coefficient (log P)

Indexed keywords

ALCOHOLS; ALKALINITY; BIOCHEMISTRY; CONTINUUM MECHANICS; DISSOCIATION; FREE ENERGY; GIBBS FREE ENERGY; QUANTUM CHEMISTRY;

ACIDIC DISSOCIATION; DISTRIBUTION COEFFICIENT; ENERGY OF SOLVATION; GASTROINTESTINAL TRACT; LIPOPHILIC CHARACTER; PARTITION COEFFICIENT; PHYSICOCHEMICAL PARAMETERS; QUANTUM-CHEMICAL METHODS;

SOLVATION;

CYTISINE; OCTANOL; WATER; ALKALOID; AZOCINE DERIVATIVE; NICOTINE; NICOTINE GUM; PROTON; QUINOLIZINE DERIVATIVE; SOLUTION AND SOLUBILITY;

AB INITIO CALCULATION; ACID DISSOCIATION CONSTANT; ARTICLE; BASE DISSOCIATION CONSTANT; DENSITY FUNCTIONAL THEORY; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; HUMAN; HYDROPHILICITY; LIPOPHILICITY; MEMBRANE PERMEABILITY; PARTITION COEFFICIENT; PH; PHYSICAL CHEMISTRY; PREDICTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; SOLVATION; THEORETICAL MODEL; ANTAGONISTS AND INHIBITORS; BIOAVAILABILITY; CHEMICAL MODEL; CHEMICAL PHENOMENA; CHEMISTRY; KINETICS; METABOLISM; MOLECULAR MODEL; MUCOSA; PERMEABILITY; SOLUBILITY; SOLUTION AND SOLUBILITY; THERMODYNAMICS;

ALKALOIDS; AZOCINES; BIOLOGICAL AVAILABILITY; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; MUCOUS MEMBRANE; NICOTINE; PERMEABILITY; PROTONS; QUINOLIZINES; SOLUBILITY; SOLUTIONS; THERMODYNAMICS; TOBACCO USE CESSATION PRODUCTS;

EID: 84947461470     PISSN: 10933263     EISSN: 18734243     Source Type: Journal    
DOI: 10.1016/j.jmgm.2015.11.003     Document Type: Article

References (29)

1. A. Husemann, and T. Husemann Die Pflanzenstoffe in Chemischer Physiologischer Pharmakologischer und Toxikologischer Hinsicht 1871 Verlag von Julius Springer Berlin 64 68
2. A. Partheil Zur Frage der Identität von Cytisin und Ulexin Arch. Pharm.(Weinheim, Ger.) 232 1894 486
3. N. Walker, C. Howe, M. Glover, H. McRobbie, J. Barnes, V. Nosa, V. Parag, B. Bassett, and Bullen Ch Cytisine versus nicotine for smoking cessation N. Engl. J. Med. 371 2014 2353 2362
4. N.A. Rigotti Cytisine - a tobacco treatment hiding in plain sight N. Engl. J. Med. 371 2014 2429 2430
5. LaMattina, J. Entrepreneur Touts Cheap, Safe Smoking Cessation Drug-But Is It? Forbes 2015.
6. 3H-cytisine Arch. Toxicol. Suppl. 4 1980 312 314
7. H. Astroug, R. Simeonova, L.V. Kassabova, N. Danchev, and D. Svinarov Pharmacokinetics of cytisine after single intravenous and oral administration in rabbits Interdisc. Toxicol. 3 1 2010 15 20
8. A.A. Freer, D.J. Robins, and G.N. Sheldrake Structures of (-)-cytisine and (-)-N-methylcytisine: tricyclic quinolizidine alkaloids Acta Cryst. C43 1987 1119 1122
9. R.B. Barlow, and O. Johnson Relations between structure and nicotine-like activity: X-ray crystal structure analysis of (-)-cytisine and (-)-lobeline hydrochloride and a comparison with (-)-nicotine and other nicotine-like compounds Br. J. Pharmacol. 98 3 1989 799 808
10. L. Zimin, Y. Li, J. Zhongjian, and Jihong Ch Stereochemical study of anagyrine-type quinolizidine alkaloids by 15N and 2D NMR spectroscopy Magn. Res. Chem. 30 6 1992 511 514
11. T. Brukwicki, and W. Wysocka Geometry of tricyclic quinolizidine-piperidine alkaloids in solution by NMR spectroscopy J. Mol. Struct. 474 1999 215 222
12. 13C NMR spectroscopy of tri- and tetracyclic quinolizidine alkaloids: compilation and discussion Magn. Res. Chem. 36 11 1998 779 796
13. E. Górnicka, M. Makowski, M. Darowska, and E.D. Raczyńska Conformational preference in isolated neutral cytisine Polish J. Chem. 75 2001 1483 1491
14. V. Galasso, A.K. Przybył, V. Christov, B. Kovac, F. Asaro, and E. Zangrando Theoretical and experimental studies on the molecular and electronic structures of cytisine and unsaturated ketosparteines Chem. Phys. 325 2006 365 377
15. M. Head-Gordon, J.A. Pople, and M.J. Frisch MP2 energy evaluation by direct methods Chem. Phys. Lett. 153 6 1988 503 506
16. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields J. Phys. Chem. 98 1994 11623 11627
17. S. Grimme, S. Ehrlich, and L. Goerigk Effect of the damping function in dispersion corrected density functional theory J. Comput. Chem. 32 7 2011 1456 1465
18. T. Yanai, D.P. Tew, and N.C. Handy A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Chem. Phys. Lett. 393 1-3 2004 51 57
19. Y. Zhao, and D.G. Truhlar The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Theor. Chem. Acc. 120 2006 215
20. J.M. Tao, J.P. Perdew, V.N. Staroverov, and G.E. Scuseria Climbing the density functional ladder: nonempirical meta-generalized gradient approximation designed for molecules and solids Phys. Rev. Lett. 91 2003 146401
21. T. Van Voorhis, and G.E. Scuseria A never form for the exchange-correlation energy functional J. Chem. Phys. 109 1998 400 410
22. A.V. Marenich, Ch.J. Cramer, and D.G. Truhlar Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 113 18 2009 6378 6396
23. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, and G.A. Petersson Gaussian 09 Revision D.01 2009 Gaussian Inc Wallingford CT
24. N. Sadlej-Sosnowska Calculation of acidic dissociation constants in water: solvation free energy terms. Their accuracy and impact Theor. Chem. Acc. 118 2007 281 293
25. M.D. Tissandier, K.A. Cowen, W.Y. Feng, E. Gundlach, M.H. Cohen, A.D. Earhart, and J.V. Coe The Proton's absolute aqueous enthalpy and gibbs free energy of solvation from cluster-Ion solvation data J. Phys. Chem. A 102 40 1998 7787 7794
26. J.E. Rode, E.D. Raczyńska, E. Górnicka, and J. Dobrowolski Cz Low inversion energy barrier of cytisine NH group - an explanation for the FT-IR bands splitting J. Mol. Struct. 749 1 2005 51 59
27. E.D. Raczyńska, M. Makowski, E. Górnicka, and M. Darowska Ab Initio studies on the preferred site of protonation in cytisine in the gas phase and water Int. J. Mol. Sci. 6 2005 143 156
28. R.B. Barlow, and L.J. Mcleod Some studies on cytisine and its methylated derivatives Br. J. Pharmacol. 35 1969 161 174
29. H. Rollema, A. Shrikhande, K.M. Ward, F.D. Tingley, J.W. Coe, B.T. O'Neill, E. Tseng, E.Q. Wang, R.J. Mather, R.S. Hurst, K.E. Williams, M. de Vries, T. Cremers, S. Bertrand, and D. Bertrand Pre-clinical properties of the alpha4beta2 nicotinic acetylcholine receptor partial agonists varenicline, cytisine and dianicline translate to clinical efficacy for nicotine dependence Br. J. Pharmacol. 160 2010 334