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. doi:10.1002/mrc.2125.
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Basic information
Original name Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study
Name in Czech Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study
Authors TOUŠEK, Jaromír (203 Czech Republic, belonging to the institution), Sabine VAN MIERT (56 Belgium), Luc PIETERS (56 Belgium), Gitte VAN BAELEN (56 Belgium), Steven HOSTYN (56 Belgium), Bert U.W. MAES (56 Belgium), Guy LEMIERE (56 Belgium), Roger DOMMISSE (56 Belgium) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
Edition Magnetic Resonance in Chemistry, John Wiley & Sons, 2008, 0749-1581.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10403 Physical chemistry
Country of publisher United Kingdom of Great Britain and Northern Ireland
Confidentiality degree is not subject to a state or trade secret
WWW DOI: 10.1002/mrc.2125
Impact factor Impact factor: 1.443
RIV identification code RIV/00216224:14310/08:00025717
Organization unit Faculty of Science
Doi http://dx.doi.org/10.1002/mrc.2125
UT WoS 000253559900007
Keywords in English NMR; 1H; 13C; 15N; quantum-chemical calculations; solvent effects; indoloquinoline alkaloids; cryptolepine
Tags 13C, 15N, 1H, cryptolepine, indoloquinoline alkaloids, NMR, quantum-chemical calculations, solvent effects
Tags International impact, Reviewed
Changed by Changed by: prof. RNDr. Radek Marek, Ph.D., učo 381. Changed: 17. 6. 2013 14:49.
Abstract
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.
Abstract (in Czech)
NMR chemické posuny indolochinolinových alkaloidů byly studovány v závislosti na struktuře a prostředí pomocí experimentální NMR spektroskopie a DFT výpočtů.
Links
LC06030, research and development projectName: Biomolekulární centrum
Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre
MSM0021622413, plan (intention)Name: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment
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