TOUŠEK, Jaromír, Sabine VAN MIERT, Luc PIETERS, Gitte VAN BAELEN, Steven HOSTYN, Bert U.W. MAES, Guy LEMIERE, Roger DOMMISSE and Radek MAREK. Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study. Magnetic Resonance in Chemistry. John Wiley & Sons, 2008, vol. 46, No 1, p. 42-51. ISSN 0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2125. |
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@article{750980, author = {Toušek, Jaromír and Van Miert, Sabine and Pieters, Luc and Van Baelen, Gitte and Hostyn, Steven and Maes, Bert U.W. and Lemiere, Guy and Dommisse, Roger and Marek, Radek}, article_number = {1}, doi = {http://dx.doi.org/10.1002/mrc.2125}, keywords = {NMR; 1H; 13C; 15N; quantum-chemical calculations; solvent effects; indoloquinoline alkaloids; cryptolepine}, language = {eng}, issn = {0749-1581}, journal = {Magnetic Resonance in Chemistry}, title = {Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study}, url = {http://dx.doi.org/10.1002/mrc.2125}, volume = {46}, year = {2008} }
TY - JOUR ID - 750980 AU - Toušek, Jaromír - Van Miert, Sabine - Pieters, Luc - Van Baelen, Gitte - Hostyn, Steven - Maes, Bert U.W. - Lemiere, Guy - Dommisse, Roger - Marek, Radek PY - 2008 TI - Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study JF - Magnetic Resonance in Chemistry VL - 46 IS - 1 SP - 42-51 EP - 42-51 PB - John Wiley & Sons SN - 07491581 KW - NMR KW - 1H KW - 13C KW - 15N KW - quantum-chemical calculations KW - solvent effects KW - indoloquinoline alkaloids KW - cryptolepine UR - http://dx.doi.org/10.1002/mrc.2125 L2 - http://dx.doi.org/10.1002/mrc.2125 N2 - Indoloquinoline alkaloids represent an important class of antimalarial, antibacterial and antiviral compounds. They have been shown to bind to DNA via intercalation preferentially at GC-rich sequences containing nonalternating CC sites. The stability of complexes formed with biological macromolecules depends on noncovalent binding. In the present study, the ability of indoloquinolines to form intermolecular interactions with solvents was investigated by using NMR spectroscopy and density functional theory (DFT) (B3LYP/6-31G**) calculations. NMR data measured for indoloquinoline bases and the corresponding hydrochlorides are discussed in relation to the structure. DFT calculations of shielding constants in vacuo and in solution allowed the investigation of the influence of the environment on the NMR parameters. Calculations incorporating solvent effects indicated significant changes in the anisotropy of the electron distribution, reflected in the span of the chemical shielding tensor (Omega = delta11 - delta33). Solvent effects on the span of the 13C and 15N shielding tensor depended on the type of atom and the data indicated a significant influence of solute-solvent interactions. ER -
TOUŠEK, Jaromír, Sabine VAN MIERT, Luc PIETERS, Gitte VAN BAELEN, Steven HOSTYN, Bert U.W. MAES, Guy LEMIERE, Roger DOMMISSE and Radek MAREK. Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study. \textit{Magnetic Resonance in Chemistry}. John Wiley \&{} Sons, 2008, vol.~46, No~1, p.~42-51. ISSN~0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2125.
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