Polymorphism of paracetamol: A new understanding of molecular flexibility through local methyl dynamics

Molecular Pharmaceutics

Volumn 11, Issue 3, 2014, Pages 1032-1041

  Tsapatsaris, Nikolaos ^a   Kolesov, Boris A ^b,c   Fischer, Jennifer ^d   Boldyreva, Elena V ^c,e   Daemen, Luke ^f   Eckert, Juergen ^f,g   Bordallo, Heloisa N ^a,h  

^a EUROPEAN SPALLATION SOURCE ERIC   (Sweden)

^b ENERGY SYSTEMS INSTITUTE   (Russian Federation)

^c NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^d FORSCHUNGSZENTRUM JÜLICH   (Germany)

^e INSTITUTE OF SOLID STATE CHEMISTRY AND MECHANOCHEMISTRY   (Russian Federation)

^f LOS ALAMOS NATIONAL LABORATORY   (United States)

^g UNIVERSITY OF SOUTH FLORIDA   (United States)

^h UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

DFT calculations; hydrogen bonding; inelastic neutron scattering; methyl rotation; molecular drugs; polymorphism

Indexed keywords

METHYL GROUP; PARACETAMOL;

AB INITIO CALCULATION; ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; DISSOCIATION CONSTANT; DRUG BIOAVAILABILITY; DRUG SOLUBILITY; ENTROPY; GEOMETRY; HYDROGEN BOND; MOLECULAR DYNAMICS; NEUTRON SCATTERING; PRIORITY JOURNAL; SOLID STATE; SOLVATION; STATIC ELECTRICITY; TEMPERATURE DEPENDENCE; THERMODYNAMICS; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; QUANTUM THEORY; SURFACE PROPERTY;

ACETAMINOPHEN; HYDROGEN BONDING; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; QUANTUM THEORY; SURFACE PROPERTIES;

EID: 84901742839     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400707m     Document Type: Article

References (60)

1. Graham, G. G.; Davies, M. J.; Day, R. O.; Mohamudally, A.; Scott, K. F. The modern pharmacology of paracetamol: therapeutic actions, mechanism of action, metabolism, toxicity and recent pharmacological findings Inflammopharmacology 2013, 21, 201
2. Vane, J. R. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs Nature-New Biol. 1971, 231, 232
3. Bronowska, A. Thermodynamics of ligand-protein interactions: Implications for molecular design. Thermodynamics-Interaction Studies-Solids, Liquids and Gases; Moreno-Pirajan, J. C., Ed.; InTech: Rijeka, Croatia, 2011.
4. Fitter, J. A measure of conformational entropy change during thermal protein unfolding using neutron spectroscopy Biophys. J. 2003, 84, 3924
5. Setny, P.; Baron, R.; Kekenes-Huskey, P. M.; McCammon, J. A.; Dzubiella, J. Solvent fluctuations in hydrophobic cavity-ligand binding kinetics Proc. Natl. Acad. Sci. U.S.A. 2013, 1197
6. Sakai, V. G.; Arbe, A. Quasielastic neutron scattering in soft matter Curr. Opin. Colloid Interface Sci. 2009, 14, 381
7. Chu, X.; Mamontov, E.; O'Neill, H.; Zhang, Q. Temperature dependence of logarithmic-like relaxational dynamics of hydrated tRNA J. Phys. Chem. Lett. 2013, 4, 936
8. Ladbury, J. E. Just add water! The effect of water on the specificity of protein-ligand binding sites and its potential application to drug design Chem. Biol. 1996, 3, 973
9. Saraboji, K.; Hakansson, M.; Genheden, S.; Diehl, C.; Qvist, J.; Weininger, U.; Nilsson, U. J.; Leffler, H.; Ryde, U.; Akke, M.; Logan, D. T. The carbohydrate-binding site in galectin-3 is preorganized to recognize a sugarlike framework of oxygens: Ultra-high-resolution structures and water dynamics Biochemistry 2012, 51, 296
10. Krishnan, M.; Smith, J. C. Reconstruction of protein side-chain conformational free energy surfaces from NMR-derived methyl axis order parameters J. Phys. Chem. B 2012, 116, 4124
11. Hase, Y. Theoretical study of the force field and vibrational assignments of acetamide and deuterated analogues Spectrochim. Acta, Part A 1995, 51, 2561
12. Uno, T.; Machida, K.; Saito, Y. Out-of-plane vibrations of acetamide and partially N-deuterated acetamide Spectrochim. Acta, Part A 1971, 27, 833
13. Tam, C. N.; Bour, P.; Eckert, J.; Trouw, F. R. Inelastic neutron scattering study of hydrogen-bonded solid formamide at 15 K J. Phys. Chem. A 1997, 101, 5877
14. Velkov, Z.; Velkov, Y.; Balabanova, E.; Tadjer, A. First principle study of the structure of conjugated amides and thioamides Int. J. Quantum Chem. 2007, 107, 1765
15. Haisa, M.; Kashino, S.; Kawai, R.; Maeda, H. Monoclinic form of para-hydroxyacetanilide Acta Crystallogr., Sect. B: Struct. Sci. 1976, 32, 1283
16. Drebushchak, T. N.; Boldyreva, E. V. Variable temperature (100-360 K) single-crystal X-ray diffraction study of the orthorhombic polymorph of paracetamol (p-hydroxyacetanilide) Z. Kristallogr. 2004, 219, 506
17. Perrin, M. A.; Neumann, M. A.; Elmaleh, H.; Zaske, L. Crystal structure determination of the elusive paracetamol Form III Chem. Commun. 2009, 3181
18. Boldyreva, E. V.; Drebushchak, V. A.; Paukov, I. E.; Kovalevskaya, Y. A.; Drebushchak, T. N. DSC and adiabatic calorimetry study of the polymorphs of paracetamol. An old problem revisited J. Therm. Anal. Calorim. 2004, 77, 607
19. Espeau, P.; Ceolin, R.; Tamarit, J. L.; Perrin, M. A.; Gauchi, J. P.; Leveiller, F. Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressureerature and temperature-volume phase diagrams J. Pharm. Sci. 2005, 94, 524
20. Boldyreva, E. V.; Shakhtshneider, T. P.; Vasilchenko, M. A.; Ahsbahs, H.; Uchtmann, H. Anisotropic crystal structure distortion of the monoclinic polymorph of acetaminophen at high hydrostatic pressures Acta Crystallogr., Sect. B: Struct. Sci. 2000, 56, 299
21. Boldyreva, E. V.; Shakhtshneider, T. P.; Ahsbahs, H.; Sowa, H.; Uchtmann, H. Effect of high pressure on the polymorphs of paracetamol J. Therm. Anal. Calorim. 2002, 68, 437
22. Bordallo, H. N.; Argyriou, D. N.; Barthès, M.; Kalceff, W.; Rols, S.; Herwig, K. W.; Fehr, C.; Juranyi, F.; Seydel, T. Hydrogen in N-methylacetamide: Positions and dynamics of the hydrogen atoms using neutron scattering J. Phys. Chem. B 2007, 111, 7725
23. Fischer, J.; Lima, J. A.; Freire, P. T. C.; Melo, F. E. A.; Havenith, R. W. A.; Filho, J. M.; Broer, R.; Eckert, J.; Bordallo, H. N. Molecular flexibility and structural instabilities in crystalline l-methionine Biophys. Chem. 2013, 180-181, 76
24. Binev, I. G.; Vassileva-Boyadjieva, P.; Binev, Y. I. Experimental and ab initio MO studies on the IR spectra and structure of 4-hydroxyacetanilide (paracetamol), its oxyanion and dianion J. Mol. Struct. 1998, 447, 235
25. Tsapatsaris, N.; Landsgesell, S.; Koza, M. M.; Frick, B.; Boldyreva, E. V; Bordallo, H. N. Polymorphic drugs examined with neutron spectroscopy: Is making more stable forms really that simple? Chem. Phys. 2013, 427, 124
26. Paukov, I. E.; Kovalevskaya, Y. A.; Arzamastcev, A. E.; Pankrushina, N. A.; Boldyreva, E. V. Heat capacity of methacetin in a temperature range of 6 to 300 K J. Therm. Anal. Calorim. 2011, 108, 243
27. Wilson, C. C. Variable temperature study of the crystal structure of paracetamol (p-hydroxyacetanilide), by single crystal neutron diffraction Z. Kristallogr. 2000, 215, 693
28. Wilson, C. C. Zero point motion of the librating methyl group in p-hydroxyacetanilide Chem. Phys. Lett. 1997, 280, 531
29. Haisa, M.; Kashino, S.; Maeda, H. Orthorhombic form of para-hydroxyacetanilide Acta Crystallogr., Sect. B: Struct. Sci. 1974, 30, 2510
30. Nichols, G.; Frampton, C. S. Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution J. Pharm. Sci. 1998, 87, 684
31. Wilson, C. C. Neutron diffraction of p-hydroxyacetanilide (paracetamol): Libration or disorder of the methyl group at 100 K J. Mol. Struct. 1997, 405, 207
32. Naumov, D. Y.; Vasilchenko, M. A.; Howard, J. A. K. The monoclinic form of acetaminophen at 150K Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, 54, 653
33. Wilson, C. C. Variable temperature study of the crystal structure of paracetamol (p-hydroxyacetanilide), by single crystal neutron diffraction Z. Kristallogr. 2000, 215, 693
34. Kolesov, B. A.; Mikhailenko, M. A.; Boldyreva, E. V. Dynamics of the intermolecular hydrogen bonds in the polymorphs of paracetamol in relation to crystal packing and conformational transitions: a variableerature polarized Raman spectroscopy study Phys. Chem. Chem. Phys. 2011, 13, 14243
35. Haisa, M.; Kashino, S. The monoclinic form of p-hydroxyacetanilide Acta Crystallogr., Sect. B: Struct. Sci. 1976, 58
36. Guest, M. F.; Bush, I. J.; Van Dam, H. J. J.; Sherwood, P.; Thomas, J. M. H.; Van Lenthe, J. H.; Havenith, R. W. A.; Kendrick, J. The GAMESS-UK electronic structure package: Algorithms, developments and applications Mol. Phys. 2005, 103, 719
37. Kresse, G.; Furthmüller, J. Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Phys. Rev. B: Condens. Matter Mater. Phys. 1996, 54, 11169
38. Vanderbilt, D. Soft self-consistent pseudopotentials in a generalized eigenvalue formalism Phys. Rev. B 1990, 41, 7892
39. Jmol: An Open-Source Java Viewer for Chemical Structures in 3D; http://www.jmol.org.
40. Barthes, M.; Bordallo, H. N.; Eckert, J.; Maurus, O.; Nunzio, G. De. Dynamics of crystalline N-methylacetamide: Temperature dependence of infrared and inelastic neutron scattering spectra J. Phys. Chem. B 1998, 5647, 6177
41. Schober, H. Neutron spectroscopy: An ideal tool for the materials scientist J. Phys. 2003, 103, 173
42. Johnson, M. R.; Prager, M.; Grimm, H.; Neumann, M. A.; Kearley, G. J.; Wilson, C. C. Methyl group dynamics in paracetamol and acetanilide: Probing the static properties of intermolecular hydrogen bonds formed by peptide groups Chem. Phys. 1999, 244, 49
43. Bordallo, H. N.; Zakharov, B. A.; Boldyreva, E. V.; Johnson, M. R.; Koza, M. M.; Seydel, T.; Fischer, J. Application of incoherent inelastic neutron scattering in pharmaceutical analysis: relaxation dynamics in phenacetin Mol. Pharm. 2012, 9, 2434
44. Bordallo, H. N.; Boldyreva, E. V.; Buchsteiner, A.; Koza, M. M.; Landsgesell, S. Structure property relationships in the crystals of the smallest amino acid: An incoherent inelastic neutron scattering study of the glycine polymorphs J. Phys. Chem. B 2008, 112, 8748
45. Drebushchak, T. N.; Boldyreva, E. V. Variable temperature (100-360 K) single-crystal X-ray diffraction study of the orthorhombic polymorph of paracetamol (p-hydroxyacetanilide) Z. Kristallogr. 2004, 219, 506
46. Laidler, K. J. Chemical Kinetics, 3 rd ed.; Harper & Row: New York, 1987.
47. Smuda, C.; Busch, S.; Wagner, B.; Unruh, T. Methyl group dynamics in glassy, polycrystalline, and liquid coenzyme Q10 studied by quasielastic neutron scattering J. Chem. Phys. 2008, 129, 074507
48. Rhodes, H. J.; Denardo, J. J.; Bode, D. W.; Blake, M. I. Differentiating non-aqueous titration of aspirin acetaminophen and salicylamide mixtures J. Pharm. Sci. 1975, 64, 1386
49. Schanker, L. S.; Shore, P. A.; Brodie, B. B.; Hogben, C. A. M. Absorption of drugs from the stomach 0.1. The rat J. Pharmacol. Exp. Ther. 1957, 120, 528
50. Johnson, M. R.; Frick, B.; Trommsdorff, H. P. A high resolution, inelastic neutron scattering investigation of tunnelling methyl groups in aspirin Chem. Phys. Lett. 1996, 258, 187
51. Prager, M.; Heidemann, A. Rotational tunneling and neutron spectroscopy: A compilation Chem. Rev. 1997, 97, 2933
52. Johnson, M. R.; Kearley, G. J. Quantitative atom-atom potentials from rotational tunneling: Their extraction and their use Annu. Rev. Phys. Chem. 2000, 51, 297
53. Ratajczyk, T.; Szymanski, S. Theory of damped quantum rotation in NMR spectra. I. Fundamental aspects J. Chem. Phys. 2005, 123, 204509
54. Szymanski, S. Nuclear magnetic resonance line shapes of methyl-like quantum rotors in lowerature solids J. Chem. Phys. 1999, 111, 288
55. Limbach, H. H.; Ulrich, S.; Grundemann, S.; Buntkowsky, G.; Sabo-Etienne, S.; Chaudret, B.; Kubas, G. J.; Eckert, J. NMR and INS line shapes of transition metal hydrides in the presence of coherent and incoherent dihydrogen exchange J. Am. Chem. Soc. 1998, 120, 7929
56. Bordallo, H. N.; Boldyreva, E. V.; Buchsteiner, A.; Koza, M. M.; Landsgesell, S. Structure-property relationships in the crystals of the smallest amino acid: an incoherent inelastic neutron scattering study of the glycine polymorphs J. Phys. Chem. B 2008, 112, 8748
57. Weller, M.; Henry, P.; Wilson, C. An analysis of the thermal motion in the negative thermal expansion material Sc2 (WO4) 3 using isotopes in neutron diffraction J. Phys. Chem. B 2000, 2, 12224
58. Koshland, D. E. Application of a theory of enzyme specificity to protein synthesis Proc. Natl. Acad. Sci. U.S.A. 1958, 44, 98
59. Park, I. H.; Li, C. L. Dynamic ligand-induced-fit simulation via enhanced conformational samplings and ensemble dockings: A survivin example J. Phys. Chem. B 2010, 114, 5144
60. Savir, Y.; Tlusty, T. Conformational proofreading: The impact of conformational changes on the specificity of molecular recognition PLoS One 2007, 2, e468