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Microscopic Interpretations of Drug Solubility
KTH, School of Biotechnology (BIO), Theoretical Chemistry.
2007 (English)Doctoral thesis, comprehensive summary (Other scientific)
Place, publisher, year, edition, pages
Stockholm: KTH , 2007. , x, 48 p.
Series
Trita-BIO-Report, ISSN 1654-2312 ; 2007:7
Keyword [en]
pharmaceutical chemistry, physical chemistry, molecular physics, computer science
National Category
Chemical Engineering
Identifiers
URN: urn:nbn:se:kth:diva-4393ISBN: 978-91-7178-691-3 (print)OAI: oai:DiVA.org:kth-4393DiVA: diva2:12113
Public defence
2007-05-29, FA 32, AlbaNova, Stockholm, 10:00
Opponent
Supervisors
Note
QC 20100630Available from: 2007-05-25 Created: 2007-05-25 Last updated: 2010-06-30Bibliographically approved
List of papers
1. Density functional theory calculations of hydrogen bonding energies of drug molecules
Open this publication in new window or tab >>Density functional theory calculations of hydrogen bonding energies of drug molecules
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2006 (English)In: Journal of Molecular Structure, ISSN 0022-2860, E-ISSN 1872-8014, Vol. 776, no 1-3, 61-68 p.Article in journal (Refereed) Published
Abstract [en]

Hydrogen bonding energies of several drug molecules have been calculated using hybrid density functional theory with inclusion of basis set superposition error corrections. The calculated total hydrogen bonding energy of each drug molecule has been compared with the result of a conceptually simple additive model, from which the summation of hydrogen bonding energies of individual polar groups present in the drug molecule are considered. It is shown that the validity of the additive model is strongly conditional, and to some extent predictable: In cases where the hydrogen bonding group is isolated the addition model can be of relevance, while in cases where the hydrogen bonding groups are interconnected through pi-conjugation rings or chains of the drug molecules it introduces substantial errors. It is suggested that such strong cooperative effects of hydrogen bonds should always be taken into account for evaluation of the hydrogen bonding energies of drug molecules.

Keyword
Hydrogen bond energies; Drug molecules; Density functional theory
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-7177 (URN)10.1016/j.theochem.2006.06.042 (DOI)000242433800007 ()2-s2.0-33749430410 (Scopus ID)
Note
QC 20100630Available from: 2007-05-25 Created: 2007-05-25 Last updated: 2017-12-14Bibliographically approved
2. Hydrogen bonding effects on infrared and Raman spectra of drug molecules
Open this publication in new window or tab >>Hydrogen bonding effects on infrared and Raman spectra of drug molecules
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2007 (English)In: Spectrochimica Acta Part A - Molecular and Biomolecular Spectroscopy, ISSN 1386-1425, E-ISSN 1873-3557, Vol. 66, no 2, 213-224 p.Article in journal (Refereed) Published
Abstract [en]

Infrared and Raman spectra of three drug molecules, aspirin, caffeine and ibuprofen, in gas phase and in aqueous solution have been simulated using hybrid density functional theory. The long range solvent effect is modelled by the polarizable continuum model, while the short range hydrogen bonding effects are taken care of by the super-molecular approach with explicit inclusion of water molecules. The calculated spectra are found to compare well with available experimental results. The agreement obtained make grounds for proposing theoretical modeling as a tool for characterizing changes in the bonding environments of drug molecules in terms of particular variations in their IR and Raman spectra.

Keyword
DFT; Drug molecules; Hydrogen bonding; Infrared; Raman; Solvent effect
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-7178 (URN)10.1016/j.saa.2006.02.045 (DOI)000243775500001 ()2-s2.0-33845886099 (Scopus ID)
Note
QC 20100630Available from: 2007-05-25 Created: 2007-05-25 Last updated: 2017-12-14Bibliographically approved
3. Solvation of N3- at the water surface: the Polarizable Continuum Model approach
Open this publication in new window or tab >>Solvation of N3- at the water surface: the Polarizable Continuum Model approach
2006 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 110, no 23, 11361-11368 p.Article in journal (Refereed) Published
Abstract [en]

We present a new quantum mechanical model to introduce Pauli repulsion interaction between a molecular solute and the surrounding solvent in the framework of the Polarizable Continuum Model. The new expression is derived in a way to allow naturally for a position-dependent solvent density. This development makes it possible to employ the derived expression for the calculation of molecular properties at the interface between two different dielectrics. The new formulation has been tested on the azide anion (N-3(-)) for which we have calculated the solvation energy, the dipole moment, and the static polarizability at the interface as a function of the ion position. The calculations have been carried out for different ion-surface orientations, and the results have also been compared with the parallel electrostatic-only solvation model.

Keyword
Electric field effects; Interfaces (materials); Molecular dynamics; Negative ions; Quantum theory; Surface properties
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-7179 (URN)10.1021/jp060794p (DOI)000238102800051 ()2-s2.0-84962377250 (Scopus ID)
Note
QC 20100630Available from: 2007-05-25 Created: 2007-05-25 Last updated: 2017-12-14Bibliographically approved
4. Calculations of the cavitation volumes and partial molar volumes of drugs in water
Open this publication in new window or tab >>Calculations of the cavitation volumes and partial molar volumes of drugs in water
(English)Manuscript (preprint) (Other academic)
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-7180 (URN)
Note
QC 20100630Available from: 2007-05-25 Created: 2007-05-25 Last updated: 2010-06-30Bibliographically approved
5. A linear scaling study of solvent-solute interaction energy of drug molecules in aqua solution
Open this publication in new window or tab >>A linear scaling study of solvent-solute interaction energy of drug molecules in aqua solution
2007 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 111, no 34, 10320-10328 p.Article in journal (Refereed) Published
Abstract [en]

Solvent-solute interaction energies for three well-known drug molecules in water solution are computed at the Hartree-Fock and B3LYP density functional theory levels using a linear scaling technique, which allows one to explicitly include in the model water molecules up to 14 A away from the solute molecule. The dependence of calculated interaction energies on the amount of included solvent has been examined. It is found that it is necessary to account for water molecules within an 8 A radius around the drug molecule to reach the saturated solvent interaction level. Effects of electron correlation and basis set on solvent-solute interaction energies are discussed.

Keyword
Density functional theory; Electron correlations; Solutions; Solvents; Water
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-7741 (URN)10.1021/jp072621l (DOI)000248929900035 ()2-s2.0-34548558980 (Scopus ID)
Note

QC 20100630

Available from: 2007-12-04 Created: 2007-12-04 Last updated: 2017-06-14Bibliographically approved
6. Basis set dependence of solvent-solute interaction energy of benzene in water: a linear scaling ab initio study
Open this publication in new window or tab >>Basis set dependence of solvent-solute interaction energy of benzene in water: a linear scaling ab initio study
(English)Article in journal (Refereed) Submitted
Identifiers
urn:nbn:se:kth:diva-7182 (URN)
Note
QC 20100630Available from: 2007-05-25 Created: 2007-05-25 Last updated: 2010-06-30Bibliographically approved

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