Electron-density descriptors as predictors in quantitative structure-activity/property relationships and drug design

Future Medicinal Chemistry

Volumn 3, Issue 8, 2011, Pages 969-994

  Matta, Chérif F ^a,b   Arabi, Alya A ^a,b  

^a MOUNT SAINT VINCENT UNIVERSITY   (Canada)

^b DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; NUCLEIC ACID BASE;

ATOM; CHEMICAL BOND; DENSITY; DRUG DESIGN; ELECTRON; MOLECULE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTITATIVE STRUCTURE PROPERTY RELATION; QUANTUM THEORY; REVIEW; STEREOCHEMISTRY; X RAY DIFFRACTION;

DRUG DESIGN; ELECTRONS; MODELS, CHEMICAL; MODELS, MOLECULAR; PHARMACEUTICAL PREPARATIONS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79959796519     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.11.65     Document Type: Review

References (149)

1. Carbó R, Leyda L, Arnau M. How similar is a molecule to another? An electron density measure of similarity between two molecular structures. Int. J. Quantum Chem. 17, 1185-1189 (1980
2. Carbó-Dorca R, Mezey PGE. Advances in Molecular Similarity, Vol. 1. Jai Press Inc, London, UK (1996
3. Carbó-Dorca R, Mezey PGE. Advances in Molecular Similarity, Vol. 2. Jai Press Inc, London, UK (1998
4. Carbó-Dorca R, Robert D, Amat LL, Gironé X, Besalú E. Molecular Quantum Similarity in QSAR and Drug Design. Springer: Berlin, Germany (2000
5. Johnson MA, Maggiora GM (EdsConcepts and Applications of Molecular Similarity. John Wiley and Sons, Inc., NY, USA (1990
6. Bader RFW, Popelier PLA, Chang C. Similarity and complementarity in chemistry. J. Mol. Struct. (Theochem), 255, 145-171 (1992
7. Attwood TK, Parry-Smith DJ. Introduction to Bioinformatics. Prentice Hall, London, UK (1999
8. Gibas C, Jambeck P. Developing Bioinformatics Computer Skills. O'Reilly: Cambridge, UK (2001
9. Mount DW. Bioinformatics: Sequence and Genome Analysis (Second EditionCold Spring Harbor Laboratory Press, New York, USA (2004
10. Janezic D, Milicevic A, Nikolic S, Trinajstic N. Graph Theoretical Matrices in Chemistry (Mathematical Chemistry Monographs, Vol. 3University of Kragujevac, Kragujevac, Serbia (2007
11. Doucet JP, Weber J. Computer-Aided Molecular Design: Theory and Applications. Academic Press Ltd, London, UK (1996
12. Gadre SR, Kulkarni SA, Suresh CH, Shrivastava IH. Basis set dependence of molecular electrostatic potential topography: a case study of substituted benzenes. Chem. Phys. Lett. 239, 273-281 (1995
13. Suresh CH, Gadre SR. Novel electrostatic approach to substituent constants: doubly substituted benzenes. J. Am. Chem. Soc. 120, 7049-7055 (1998 (Pubitemid 28378361)
14. Gadre SR. Topography of atomic and molecular scalar fields. In: Computational Chemistry: Reviews of Current Trends. World Scientific, Singapore 1-53 (1999
15. Gadre SR, Shirsat RN. Electrostatics of Atoms and Molecules. Universities Press, Hyderabad, India (2000
16. Roy D, Balanarayan P, Gadre SR. An appraisal of Poincaré-Hopf relation and application to topography of molecular electrostatic potentials. J. Chem. Phys. 129, 174103 (2008
17. Matta CF, Arabi AA, Weaver DF. The bioisosteric similarity of the tetrazole and carboxylate anions: clues from the topologies of the electrostatic potential and of the electron density. Eur. J. Med. Chem. 45, 1868-1872 (2010
18. Hohenberg P, Kohn W. Inhomogeneous electron gas. Phys. Rev. B136, 864-871 (1964
19. Riess I, Münch W. The theorem of Hohenberg and Kohn for subdomains of a quantum system. Theor. Chim. Acta. 58, 295-300 (1981
20. Bader RFW, Becker P. Transferability of atomic properties and the theorem of Hohenberg and Kohn. Chem. Phys. Lett. 148, 452-458 (1988
21. Mezey PG. The holographic electron density theorem and quantum similarity measures. Mol. Phys. 96, 169-178 (1999 (Pubitemid 129707839)
22. Constans P, Amat L, Carbó-Dorca R. Toward a global maximization of the molecular similarity function: superposition of two molecules. J. Comput. Chem. 18, 826-846 (1997 (Pubitemid 127560729)
23. McMahon AJ, King PM. Optimization of Carbó molecular similarity index using gradient methods. J. Comput. Chem. 18, 151-158 (1997 (Pubitemid 127598561)
24. Bader RFW. Encyclopedia of Computational Chemistry. Schleyer PvR (Ed.John Wiley and Sons, Chichester, UK 64-86 (1998
25. Bader RFW. A quantum theory of molecular structure and its applications. Chem. Rev. 91, 893-928 (1991
26. Bader RFW. Atoms in Molecules: a Quantum Theory. Oxford University Press, Oxford, UK (1990
27. Popelier PLA. Atoms in Molecules: An Introduction. Prentice Hall, London, UK (2000
28. Bader RFW, Matta CF, Martín FJ. Atoms in medicinal chemistry. Medicinal Quantum Chemistry. Wiley-VCH, Weinheim, Germany 201-231 (2003
29. Matta CF, Boyd RJ (EdsThe Quantum Theory of Atoms in Molecules: from Solid State to DNA and Drug Design. Matta CF, Boyd RJ (EdsWiley-VCH, Weinheim, Germany (2007
30. Coppens P. X-ray Charge Densities and Chemical Bonding. Oxford University Press, Inc, NY, USA (1997
31. Koritsanszky TS, Coppens P. Chemical applications of x-ray charge-density analysis. Chem. Rev. 101, 1583-1628 (2001
32. Frisch MJ, Trucks GW, Schlegel HB et al. Gaussian 09, Gaussian Inc., Wallingford, CT, USA (2009
33. Schmidt MW, Baldridge KK, Boatz JA et al. General atomic and molecular electronic-structure system (GAMESSJ. Comput. Chem. 14, 1347-1363 (1993
34. Bader RFW. A bond path: a universal indicator of bonded interactions. J. Phys. Chem. A 102, 7314-7323 (1998 (Pubitemid 128578168)
35. Runtz GR, Bader RFW, Messer RR. Definition of bond paths and bond directions in terms of the molecular charge distribution. Can. J. Chem. 55, 3040-3045 (1977
36. Popelier PLA. Integration of atoms in molecules: a critical examination. Mol. Phys. 87, 1196-1187 (1996
37. Kosov DS, Popelier PLA. Atomic partitioning of molecular electrostatic potentials. J. Phys. Chem. A 104, 7339-7345 (2000
38. Kosov DS, Popelier PLA. Convergence of the multipole expansion for electrostatic potentials of finite topological atoms. J. Chem. Phys. 113, 3969-3974 (2000
39. Popelier PLA, Joubert L, Kosov DS. Convergence of the electrostatic interaction based on topological atoms. J. Phys. Chem. A 105, 8254-8261 (2001 (Pubitemid 35378222)
40. Bader RFW, Nguyen-Dang TT. Quantum theory of atoms in molecules - Dalton revisited. Adv. Quantum Chem. 14, 63-124 (1981
41. Bader RFW. Principle of stationary action and the definition of a proper open system. Phys. Rev. B 49, 13348-13356 (1994
42. Cremer D, Kraka E. Chemical bonds without bonding electron density - does the difference electron-density analysis suffice for a description of the chemical bond? Angew. Chem. Int. Ed. Engl. 23, 627-628 (1984
43. Fradera X, Austen MA, Bader RFW. The Lewis model and beyond. J. Phys. Chem. A 103, 304-314 (1999 (Pubitemid 129589280)
44. Matta CF, J. Hernández-Trujillo. Bonding in polycyclic aromatic hydrocarbons in terms of the electron density and of electron delocalization. J. Phys. Chem. A 107, 7496-7504 (2003) (Erratum in: J. Phys. Chem A, 109, 10798 [2005]
45. Zhurova EA, Matta CF, Wu N, Zhurov VV, Pinkerton AA. Experimental and theoretical electron density study of estrone. J. Am. Chem. Soc. 128, 8849-8861 (2006 (Pubitemid 44063473)
46. Hammett LP. Physical Organic Chemistry: Reaction Rates, Equilibria, and Mechanisms (Second EditionMcGraw-Hill Book Company, NY, USA (1970
47. Popelier PLA. Quantum molecular similarity. 1. BCP space. J. Phys. Chem. A 103, 2883-2890 (1999 (Pubitemid 129570859)
48. O'Brien SE, Popelier PLA. Quantum molecular similarity. Part 2: the relation between properties in BCP space and bond length. Can. J. Chem. 77, 28-36 (1999
49. O'Brien SE, Popelier PLA. Quantum molecular similarity. 3. QTMS descriptors. J. Chem. Inf. Comput. Sci. 41, 764-775 (2001
50. O'Brien SE, Popelier PLA. Quantum molecular similarity: use of atoms in molecules derived quantities as QSAR variables. In: European Congress on Computational Methods in Applied Sciences and Engineering (ECCOMAS 2000) Barcelona, Spain (2000
51. Chaudry UA, Popelier PLA. Estimation of pKa using quantum topological molecular similarity descriptors: application to carboxylic acids, anilines and phenols. J. Org. Chem. 69, 233-241 (2004 (Pubitemid 38101703)
52. Singh N, Loader RJ, O'Malley PJ, Popelier PLA. Computation of relative bond dissociation enthalpies (BDE) of phenolic antioxidants from quantum topological molecular similarity (QTMSJ. Phys. Chem. A 110, 6498-6503 (2006 (Pubitemid 44020303)
53. Hawe GI, Alkorta I, Popelier PLA. Prediction of the basicities of pyridines in the gas phase and in aqueous solution. J. Chem. Inf. Model. 50, 87-96 (2010
54. Popelier PLA. Developing Quantum Topological Molecular Similarity (QTMSIn: Quantum Biochemistry: Electronic Structure and Biological Activity (Volume 2Matta CF (Ed.Wiley-VCH, Weinheim, Germany 669-691 (2010
55. Adam KR. New density functional and atoms in molecules method of computing relative pKa values in solution. J. Phys. Chem. A 106, 11963-11972 (2002
56. Millero FJ, Surodo AL, Shin C. The apparent molal volumes and adiabatic compressibilities of aqueous amino acids at 25°C. J. Phys. Chem. 82, 784-792 (1978
57. Collantes ER, Dunn WJI. Amino acid side chain descriptors for quantitative structure- activity relationship studies of peptide analogues. J. Med. Chem. 38, 2705-2713 (1995
58. Hinz HJ Thermodynamic Data for Biochemistry and Biotechnology. Springer- Verlag, Berlin, Germany (1986
59. Matta CF, Bader RFW. Atoms-in-molecules study of the genetically-encoded amino acids. III. Bond and atomic properties and their correlations with experiment including mutation-induced changes in protein stability and genetic coding. Proteins: Struct. Funct. Genet. 52, 360-399 (2003 (Pubitemid 36944855)
60. Matta CF. From atoms in amino acids to the genetic code and protein stability, and backwards. In: Quantum Biochemistry: Electronic Structure and Biological Activity (Volume 1Matta CF (Ed.Wiley-VCH: Weinheim 423-472 (2010
61. Lee A, Chalikian TV. Volumetric characterization of the hydration properties of hetercyclic bases and nucleosides. Biophys. Chem. 92, 209-227 (2001 (Pubitemid 32907300)
62. Leo A, Hansch C, Elkins D. Partition coefficients and their uses. Chem. Rev. 71, 525-616 (1971
63. Helmer F, Kiehs K, Hansch C. The linear free-energy relationship between partition coefficients and the binding and conformational perturbation of macromolecules by small organic compounds. Biochem. 7, 2858-2863 (1968
64. Hansch C. A quantitative approach to biochemical structure-activity relationships. Acc. Chem. Res. 2, 232-239 (1969
65. Tute MS. Principles and practice of Hansch analysis: a guide to structure-activity correlation for the medicinal chemist. In: Advances in Drug Research (Vol. 6Academic Press, London, UK 1-77 (1971
66. Patrick GL. An Introduction to Medicinal Chemistry. Oxford University Press, Oxford, UK (2005
67. Radzicka A, Wolfenden R. Comparing the polarities of the amino acids: side-chain distribution coefficients between the vapor phase, cyclohexane, 1-octanol, and neutral aqueous solutions. Biochem. 27, 1664-1670 (1988
68. Breneman CM, Weber LW. Transferable atom equivalents. Molecular electrostatic potentials from the electric multipoles of PROAIMS atomic basins. In: NATO ASI Series: The Application of Charge Density Research to Chemistry and Drug Design. Plenum Press, NY, USA 357-358 (1991
69. Breneman CM, Thompson TR, Rhem M, Dung M. Electron density modeling of large systems using the transferable atom equivalent method. Comput. Chem. 19, 161-179 (1995
70. Breneman CM, Rhem M. QSPR analysis of HPLC column capacity factors for a set of high-energy materials using electronic van der Waals' surface property descriptors computed by transferable atom equivalent method. J. Comput. Chem. 18, 182-197 (1997 (Pubitemid 127598564)
71. Sukumar N, Breneman CM. QTAIM in drug discovery and protein modeling. In: The Quantum Theory of Atoms in Molecules: from Solid State to DNA and Drug Design. Matta CF, Boyd RJ (EdsWiley-VCH, Weinheim, Germany 473-498 (2007
72. Ramsey NF. Electron coupled interactions between nuclear spins in molecules. Phys. Rev. 91, 303-307 (1953
73. Stephen MJ. A variational method for calculating nuclear spin-spin interactions in molecules. Proc. Roy. Soc. London A 243, 274-280 (1957
74. Wilkens SJ, Westler WM, Markley JL, Weinhold F. Natural J-coupling analysis: interpretation of scalar J-couplings in terms of natural bond orbitals. J. Am. Chem. Soc. 123, 12026-12036 (2001 (Pubitemid 33135034)
75. Helgaker T, Jaszuński M, Ruud K. Ab initio methods for the calculation of NMR shielding and indirect spin-spin coupling constants. Chem. Rev. 99, 293-352 (1999 (Pubitemid 129657134)
76. Watson MA, Salek P, Macak P, Jaszuński M, Helgaker T. The calculation of indirect nuclear spin-spin coupling constants in large molecules. Chem. Eur. J. 10, 4627-4639 (2004
77. Alkorta I, Elguero J. Review on DFT and ab initio calculations of scalar coupling constants. Int. J. Mol. Sci. 4, 64-92 (2003 (Pubitemid 38957251)
78. Matta CF, Hernández-Trujillo J, Bader RFW. Proton spin-spin coupling and electron delocalisation. J. Phys. Chem. A 106, 7369-7375 (2002 (Pubitemid 35382580)
79. Matta CF. Applications of the quantum theory of atoms in molecules to chemical and biochemical problems. PhD thesis. McMaster University, Hamilton, Canada (2002
80. N. Castillo, Matta CF, Boyd RJ. Fluorine- fluorine spin-spin coupling constants: correlations with the delocalization index and with the internuclear separation. J. Chem. Inf. Mod. 45, 354-359 (2005 (Pubitemid 40635342)
81. Pople AJ, Schneider WG, Bernstein HJ. High-Resolution Nuclear Magnetic Resonance. McGraw-Hill Book Co. Inc, New York, USA (1959
82. Tomasi J, Cappelli C, Mennucci B, Cammi R. From molecular electrostatic potentials to solvations models and ending with biomolecular photophysical processes. In: Quantum Biochemistry: Electronic Structure and Biological Activity (Volume 1Matta CF (Ed.Wiley-VCH, Weinheim, Germany 131-170 (2010
83. Bonaccorsi R, Scrocco E, Tomasi J. Approximate expression of electrostatic molecular potential in terms of completely transferable group contributions. J. Am. Chem. Soc. 99, 4546-4554 (1977
84. Bonaccorsi R, Scrocco E, Tomasi J. Group contributions to electrostatic molecular potential. J. Am. Chem. Soc. 98, 4049-4054 (1976
85. Petrongolo C, Tomasi J. The use of electrostatic molecular potential in quantum pharmacology. 1. Ab initio results. Int. J. Quantum Chem. Quantum Biol. Symp. No. 2. 181-190 (1975
86. Chemical Applications of Atomic and Molecular Electrostatic Potentials. Reactivity, Structure, Scattering, and Energetics of Organic, Inorganic, and Biological Systems. Politzer P, Truhlar DG (EdsPlenum Press, New York, USA (1981
87. Murray JS, Politzer P. Electrostatic potentials: chemical applications. In:Encyclopedia of Computational Chemistry . Schleyer PvR (Ed.) John Wiley & Sons, Chichester, UK (1998
88. Politzer P, Murray JS, Peralta-Inga Z. Molecular surface electrostatic potentials in relation to noncovalent interactions in biological systems. Int. J. Quantum Chem. 85, 676-684 (2001 (Pubitemid 33105812)
89. Gonzalez OG, Murray JS, Peralta-Inga Z, Politzer P. Computed molecular surface electrostatic potentials of two groups of reverse transcriptase inhibitors: relationships to anti-HIV-1 activities. Int. J. Quantum Chem. 83, 115-121 (2001 (Pubitemid 32517561)
90. Murray JS, Politzer P. The use of the molecular electrostatic potential in medicinal chemistry. In: Quantum Medicinal Chemistry. Carloni P, Alber F (EdsWiley-VCH, Weinheim, Germany 233-254 (2003
91. Babu K, Ganesh V, Gadre SR, Ghermani NE. Tailoring approach for exploring electron densities and electrostatic potentials of molecular crystals. Theor. Chem. Acc. 111, 255 (2004
92. Politzer P, Murray JS. Molecular electrostatic potentials and chemical reactivity. In: Reviews in Computational Chemistry. John Wiley & Sons, Inc, Hoboken, NJ, USA (2007
93. Herr R. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. J. Bioorg. Med. Chem. 10, 3379-3393 (2002
94. Biot C, Bauer H, Schirmer RH, Davioud- Charvet E. 5-Substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials. J. Med. Chem. 47, 5972-5983 (2004 (Pubitemid 39507339)
95. Yuan H, Silverman RB. New substrates and inhibitors of g-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity. Bioorg. Med. Chem. 14, 1331-1338 (2006 (Pubitemid 43120270)
96. Yuan H, Silverman RB. Structural modifications of (1S, 3S)-3-amino-4-difluoro methylenecyclopentanecarboxylic acid, a potent irreversible inhibitor of GABA aminotransferase. Bioorg. Med. Chem. Lett. 17, 1651-1654 (2007 (Pubitemid 46274367)
97. Burgos-Lepley CE, Thompson LR, Kneen CO et al. Carboxylate bioisosteres of gabapentin. Bioorg. Med. Chem. Lett. 16, 2333-2336 (2006
98. Kohn W, Sham LJ. Self consistent equations including exchange and correlation effects. Phys. Rev. A 140 (4A), 1133-1138 (1965
99. Bader RFW, Jones GA. The electron density distributions in hydride molecules, I, the water molecule. Can. J. Chem. 41, 586-606 (1963
100. Bader RFW, Jones GA. The electron density distributions in hydride molecules, III, the hydrogen fluoride molecule. Can. J. Chem. 41, 2251-2264 (1963
101. Bader RFW, Jones GA. The electron density distribution in hydride molecules. The ammonia molecule. J. Chem. Phys. 38, 2791-2802 (1963
102. Bader RFW. binding regions in polyatomic molecules and electron density distributions. J. Am. Chem. Soc. 86, 5070-5075 (1964
103. Dovesi R, Saunders VR, Roetti. CRYSTAL98 (1998
104. Becke A. A new mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 98, 1372-1377 (1993
105. Lee C, Yang W, Parr R. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 37, 785-789 (1988
106. Matta CF. Quantum Biochemistry: Electronic Structure and Biological Activity (Volumes 1 & 2Wiley-VCH, Weinheim, Germany (2010
107. Carloni P, Alber FE (EdsQuantum Medicinal Chemistry. Wiley-VCH, Weinheim, Germany (2003
108. Brändas EJ, Kryachko ES (EdsFundamental World of Quantum Chemistry: A Tribute to the Memory of Per-Olov Löwdin. Kluwer Academic Publishers, Dordrecht, The Netherlands (2003
109. Becker OM. MacKerell AD Jr, Roux B, Watanabe M. Computational Biochemistry and Biophysics. Marcel Dekker Inc, NY, USA (2001
110. Eriksson LA (EdsTheoretical Biochemistry - Processes and Properties of Biological Systems. Elsevier Science BV, Amsterdam, The Netherlands (2001
111. Greenberg A, Breneman C, Liebman JFE. The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science. John Wiley and Sons, Inc, New York, USA (2000
112. Sapse AM. Molecular Orbital Calculations for Amino Acids and Peptides. Birkhäuser, Boston, USA (2000
113. Biegler-König FW, Bader RFW, T.-Tang H. Calculation of the average properties of atoms in molecules. II. J. Comput. Chem. 13, 317-328 (1982
114. Popelier PLA. MORPHY, a program for an automatic atoms in molecules analysis. Comp. Phys. Comm. 1996, 93, 212-240.
115. Popelier PLA. MORPHY, Manchester University, England, UK (1998
116. Biegler-König FW. Calculation of atomic integration data. J. Comput. Chem. 21, 1040-1048 (2000
117. Biegler-König FW, Schönbohm J, Bayles D. AIM2000 - a program to analyze and visualize atoms in molecules. J. Comput. Chem. 22, 545-559 (2001 (Pubitemid 32291692)
118. Keith TA. AIMAll (2009
119. Gatti C. TOPOND, CNR-CSRSRC. Milano, Italy (1998
120. Espinosa E, Molins E, Lecomte C. Hydrogen bond strengths related by topological analyses of experimentally observed electron densities. Chem. Phys. Lett. 285, 170-173 (1998 (Pubitemid 128180262)
121. Housset D, Benabicha F, Pichon-Pesme V et al. Towards the charge-density study of proteins: A room-temperature scorpion-toxin structure at 0.96Å resolution as a first test case. Acta Cryst. D56, 151-160 (2000 (Pubitemid 30105007)
122. Benabicha F, Pichon-Pesme V, Jelsch C, Lecomte C, Khmou A. Experimental charge density and electrostatic potential of glycyl-l-threonine dihydrate. Acta Cryst. B56, 155-165 (2000
123. Leherte L, Guillot B, Vercauteren DP et al. Topological analysis of proteins as derived from medium and high-resolution electron density: applications to electrostatic properties. In: The Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design. Matta CF, Boyd RJ (EdsWiley-VCH, Weinheim, Germany 285-315 (2007
124. Dittrich B, Koritsánszky T, Grosche M et al. Reproducability and transferability of topological properties. experimental charge density of the hexapeptide cyclo-(D, L-Pro)2-(L-Ala)4 monohydrate. Acta Cryst. B58, 721-727 (2002 (Pubitemid 135688519)
125. Scheins S, Messerschmidt M, Luger P. Submolecular partitioning of morphine hydrate based on its experimental charge density at 25 K. Acta Cryst. B61, 443-448 (2005 (Pubitemid 41557398)
126. P. Luger, Dittrich B. Fragment transferability studied theoretically and experimentally with QTAIM - implications for electron density and invariom modeling. In: The Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design. Matta CF, Boyd RJ (EdsWiley-VCH, Weinheim, Germany 317-341 (2007
127. Luger P. Fast electron density methods in the life sciences - a routine application in the future? Org. Biomolec. Chem. 5, 2529-2540 (2007 (Pubitemid 47192303)
128. Koritsanszky TS, Howard S, Macchi P et al. XD Program. Free University of Berlin, Germany. University of Wales, Cardiff, UK. Universita di Milano, UK. CNR-ISTM, Milano, UK. University of Glasgow UK. State University of New York, Buffalo, USA. University of Nancy, France (2003
129. B. Guillot, Viry L, Guillot R, Lecomte C, Jelsch CJ. Refinement of proteins at subatomic resolution with MoPro. J. App. Cryst. 34, 214-223 (2001 (Pubitemid 32290311)
130. Jelsch C, Guillot B, Lagoutte L, Lecomte C. Advances in proteins and small molecules. charge density refinement methods using software MoPro. J. App. Cryst. 38, 38-54 (2005 (Pubitemid 40260748)
131. Wiberg KB, Bader RFW, Lau CDH. Theoretical analysis of hydrocarbons properties. 2. Additivity of group properties and the origin of strain energy. J. Am. Chem. Soc. 109, 1001-1012 (1987
132. Keith TA, Bader RFW. Calculation of magnetic response properties using atoms in molecules. Chem. Phys. Lett. 194, 1-8 (1992
133. Keith TA, Bader RFW. Use of electron charge and current distributions in the determination of atomic contributions to magnetic properties. Int. J. Quantum Chem. 60, 373-379 (1996 (Pubitemid 126547092)
134. Bader RFW, Keith TA, Gough KM, Laidig KE. Properties of atoms in molecules: additivity and transferability of group polarizabilities. Mol. Phys. 75, 1167-1189 (1992
135. Gough KM, Yacowar MM, Cleve RH, Dwyer RJ. Analysis of molecular polarizabilities and polarizability derivatives in H2, N2, F2, CO, and HF, with the theory of atoms in molecules. Can. J. Chem. 74, 1139-1144 (1996 (Pubitemid 126423929)
136. Gough KM, Srivastava HK, Belohorcová K. Molecular polarizability and polarizability derivatives in cyclohexane analyzed with the theory of atoms in molecules. J. Phys. Chem. 98, 771-776 (1994
137. Gough KM, Srivastava HK. Electronic charge flow and Raman trace scattering intensities for CH stretching vibrations in n-pentane. J. Phys. Chem. 100, 5210-5216 (1996 (Pubitemid 126790483)
138. Haiduke RLA, Bruns RE. An atomic charge-charge flux-dipole flux atom-in-molecule decomposition for molecular dipole-moment derivatives and infrared fundamental intensities. J. Phys. Chem. A 109, 2680-2688 (2005 (Pubitemid 40407795)
139. da Silva JV, Haiduke RLA, Bruns RE. QTAIM charge-charge flux-dipole flux models for the infrared fundamental intensities of the fluorochloromethanes. J. Phys. Chem. A 110, 4839-4845 (2006
140. Austen MA. A new procedure for determining bond orders in polar molecules, with applications to phosphorus and nitrogen containing systems. PhD thesis. McMaster University, Hamilton, Canada (2003
141. Wang YG, Matta CF, Werstiuk NH. Comparison of localization and delocalization indices obtained with Hartree-Fock and conventional correlated methods: effect of Coulomb correlation. J. Comput. Chem. 24, 1720-1729 (2003
142. Bohórquez HJ, Obregón M, Cárdenas C et al. Electronic energy and multipolar moments characterize amino acid side chains into chemically related groups. J. Phys. Chem. A. 107, 10090-10097 (2003
143. Bohorquez HJ, Cardenas C, Matta CF, Boyd RJ, Patarroyo ME. Methods in biocomputational chemistry: a lesson from the amino acids. In: Quantum Biochemistry: Electronic Structure and Biological Activity. Matta CF, Boyd RJ (EdsWiley-VCH, Weinheim, Germany 403-421 (2010
144. Matta CF, Bader RFW. An atoms-in-molecules study of the genetically-encoded amino acids. I. Effects of conformation and of tautomerization on geometric, atomic, and bond properties. Proteins: Struct. Funct. Genet. 40, 310-329 (2000 (Pubitemid 30413632)
145. Matta CF, Bader RFW. Atoms-in-molecules study of the genetically-encoded amino acids. II. Computational study of molecular geometries. Proteins: Struct. Funct. Genet. 48, 519-538 (2002 (Pubitemid 34810417)
146. Song M, Breneman CM, Bi J et al. Prediction of protein retention times in anion-exchange chromatography systems using support vector regression. J. Chem. Inf. Comput. Sci. 42, 1347-1357 (2002 (Pubitemid 35468322)
147. Popelier PLA, Aicken FM. Atomic properties of amino acids: computed atom types as a guide for future force-field design. Chemphyschem 4, 824-829 (2003
148. Popelier PLA, Aicken FM. Atomic properties of selected biomolecules: quantum topological atom types of carbon occurring in natural amino acids and derived molecules. J. Am. Chem. Soc. 125, 1284-1292 (2003 (Pubitemid 36159839)
149. Matta CF. Theoretical reconstruction of the electron density of large molecules from fragments determined as proper open quantum systems: the properties of the oripavine PEO, enkephalins, and morphine. J. Phys. Chem. A 105, 11088-11101 (2001) (Pubitemid 35378598)