Electron density of a new EGFR Tyrokinase-inhibitor at 100 K, consideration of different models

Zeitschrift fur Kristallographie

Volumn 223, Issue 8, 2008, Pages 502-514

  Mebs, Stefan ^a   Lüth, Anja ^a   Löwe, Wolfgang ^a   Paulmann, Carsten ^b   Luger, Peter ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Anti cancer drugs; Charge density; Single crystal structure analysis; Synchrotron experiments; X ray diffraction

Indexed keywords

EID: 55849092839     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.2008.0055     Document Type: Article

References (41)

1. Lüth, A.: Synthesis of substituted 4-(indol-3-yl)quinazolines, a new class of EGFR-tyrosine-kinase-inhibitors. Ph.D. thesis, Freie Universität, Berlin (2006).
2. Grabowsky, S.; Pfeuffer, T.; Chêciñska, L.; Weber, M.; Morgenroth, W; Luger, P.; Schirmeister, T.: Electron-Density Determination of Electrophilic Building Blocks as Model Compunds for Protease Inhibitors. Eur. J. Org. Chem. (2007) 2759-2768.
3. Stamos, J.; Sliwkowski, M. X.; Eigenbrot, Ch.: Structure of the Epeidermal Growth Factor Receptor Kinase Domain Alone and in Complex with a 4-Anilinoquinazoline Inhibitor. J. Biol. Chem. 277/48 (2002) 46265-46272.
4. Hou, T.; Zhu, L.; Chen, L.; Xu, X.: Mapping the Binding Site of a Large Set of Quinazoline Type EGF-R Inhibitors Using Molecular Field Analyses and Molecular Docking Studies. J. Chem. Inf. Comput. Sci. 43 (2003) 273-287.
5. Kabsch, W.: Automatic Processing of Rotation Diffraction Data from Crystals of Initially Unknown Symmetry and Cell Constants. J. Appl. Crystallogr. 26 (1993) 795-800.
6. Blessing, R. H.; Langs, D. A.: Data Averaging with normal down-weighting of outliers. J. Appl. Crystallogr. 20 (1987) 427-428.
7. Sheldrick, G. M.: SHELXS97: Program for Crystal Structure Solution, and SHELXL97: Program for Refinement of Crystal Structures. University of Göttingen, Release 97-2, Germany (1997).
8. Hansen, N. K.; Coppens, P.: Testing Aspherical Atom Refinements on Small-Molecule Data Sets. Acta Crystallogr. A34 (1978) 909-921.
9. Koritsansky, T.; Mallison, R. P.; Howard, S.; Volkov, A.; Macchi, P.; Su, Z.; Gatti, C.; Richter, T.; Farrugia L. J.; Hansen, N. K.: XD, A Computer Program package for Multipole Refinement and Analysis of Electron Densities from Diffraction Data. User Manual (2003).
10. Clementi, E.; Roetti, C.: Roothaan-Hartree-Fock Atomic Wave-functions. Atomic Data and Nuclear Data Tables 14 (1974) 177-478.
11. Volkov, A.; Abramov, Y. A.; Coppens, P.: Density-optimized radial exponents for X-ray charge-density refinement from ab initio crystal calculations. Acta Crystallogr. A57 (2001) 272-282.
12. Frisch, M. J., et al.: GAUSSIAN98, revision a.7, GAUSSIAN, Inc., Pittsburgh PA, USA (1998).
13. Jayatilaka, D.; Grimwood, D. J.: TONTO: A Fortran Based Object-Oriented System for Quantum Chemistry and Crystallography. User Manual (2003).
14. Allen, F. H.; Kennard, O.; Watson, D.; Brammer, L.; Orpen, A.; Taylor, R.: International Tables of Crystallography, Vol. C, ch. 9.5, 685-706. Dordrecht: Luwer Academic Publishers (1992).
15. Volkov, A.; Coppens, P.: Critical examination of the radial functions in the Hansen-Coppens multipole model through topological analysis of primary and refined theoretical densities. Acta Crystallogr. A57 (2001) 395-405.
16. Koritsanszky, T.; Volkov, A.: Atomic density radial functions from molecular densities. Chem. Phys. Lett. 385 (2004) 431-434.
17. Biegler-König, F.; Schönbohm, J.; Bayles, D.: AIM2000 - A Program to Analyse and Visualise Atoms in Molecules. J. Comp. Chem 22 (2001) 549-559.
18. Schaftenaar, G., Noordik, J. H.: MOLDEN. J. Comput.-Aided Mol. Design 14 (2000) 123-134.
19. Burnett, M. N.; Johnson, C. K.: ORTEP-III, Oak Ridge Thermal Ellipsoid Plotting Program for Crystal Structure Illustrations, Report ORNL-6895, Oak Ridge National Laboratory, Tennessee TN, USA (1996).
20. Keller, E.: SCHAKAL. A Fortran Program for the Graphical Representation of Molecular and Solid-State Structure Models. Albert Ludwigs Universität Freiburg, Germany (1999).
21. Mebs, S.; Messerschmidt, M.; Luger, P.: Experimental charge density of an L-phenylalanine formic acid complex with a short hydrogen bond determined at 25 K. Z. Kristallogr. 221 (2006) 656-664.
22. Scheins, S.; Dittrich, B.; Messerschmidt, M.; Paulmann, C.; Luger, P.: Atomic volumes and charges in a system with a strong hydrogen bond: L-tryptophan formic acid. Acta Crystallogr. B60 (2004)184-190.
23. Hübschle, Ch.: Neue Ansätze zur Elektronendichtebestimmung: Entwicklung von Datenbankanwendungen und graphischen Verfahren. Ph.D. thesis, Freie Universität, Berlin (2007).
24. Bach, A.; Lentz, D.; Luger, P.: Charge Density and Topological Analysis of Pentafluorobenzoic Acid. J. Phys. Chem. A105 (2001) 7405-7412.
25. Volkov, A.; Abramov, Y.; Coppens, P.; Gatti, C.: On the origin of topological differences between experimental and theoretical crystal charge densities. Acta Crystallogr. A56 (2000) 332-339.
26. Coppens, P.; Volkov, A.: The interplay between experiment and theory in charge-density analysis. Acta Crystallogr. A60 (2004) 357-364.
27. Henn, J.; Ilge, D.; Leusser, D.; Stalke, D.; Engels, B.: On the Accuracy of Theoretically and Experimentally Determined Electron Densities of Polar Bonds. J. Phys. Chem. A108 (2004) 9442-9452.
28. Luger, P.: Fast electron density methods in the Life Sciences - a routine application in the future? Org. Biomol. Chem. 5 (2007) 2529-2540.
29. Bader, R. F. W. : Atoms in Molecules: A Quantum Theory, Clarendon Press, Oxford, U.K (1990).
30. Volkov, A.; Gatti, C.; Abramov, Y.; Coppens, P.: Evaluation of net atomic charges and atomic and molecular electrostatic moments through topological analysis of the experimental charge density. Acta Crystallogr. A56 (2000) 252-258.
31. Luger, P., Messerschmidt, M.; Scheins, S.; Wagner, A.: High-resolution synchrotron data collection for charge-density work at 100 K and 20 K. Acta Crystallogr. A60 (2004) 390-396.
32. Espinosa, E.; Molins, E.; Lecomte, C.: Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chem. Phys. Lett. 285 (1998) 170-173.
33. Espinosa, E.; Souhassou, M.; Lachekar, H.; Lecomte, C.: Topological analysis of the electron density in hydrogen bonds. Acta Crystallogr. B55 (1999) 563-572.
34. Espinosa, E.; Lecomte, C.; Molins, E.: Experimental electron density overlapping in hydrogen bonds: topology vs. energetics. Chem. Phys. Lett. 300 (1999) 745-748.
35. Espinosa, E.; Alkorta, I., Elguero, J., Molins, E.: From weak to strong interactions: A comprehensive analysis of the topological and energetic properties of the electron density distribution in-volving X-H⋯F-Y systems. J. Chem. Phys. 117/12 (2002) 5529-5542.
36. Spackman, M. A.: Hydrogen bond energetics from topological analysis of experimental electron densities: Recognising the importance of the promolecule. Chem. Phys. Lett. 301 (1999) 425-429.
37. Abramov, Yu. A.: On the Possibility of Kinetic Energy Densiy Evaluation from the Experimental Electron-Density Distribution. Acta Crystallogr. A53 (1997) 264-272.
38. Su, Z.; Coppens, P.: On the Mapping of Electrostatic Properties from the Multipole Description of the Charge Density. Acta Crystallogr. A48 (1992) 188-197.
39. Abramov, Yu. A.; Volkov, A. V.; Coppens, P.: On the evaluation of molecular dipole moments from multipole refinements of X-ray diffraction data. Chem. Phys. Lett. 311 (1999) 81-86.
40. Dominiak, P. M.; Coppens, P.: Finding optimal radial-function parameters for S atoms in the Hansen-Coppens multipole model through refinement of theoretical densities. Acta Crystallogr. A62 (2006) 224-227.
41. Kocher, N.; Selinka, C.; Leusser, D.; Kost, D.; Kalikhman, I., Stalke, D.: Experimental Charge Density Studies of Cyclotetrasilazane and Metal Complexes Containing the Di- and Tetraanion. Z. Anorg. Allg. Chem. 630 (2004) 1777-1793.