Structural and solvent effects on the 13C and 15N NMR chemical
shifts of indoloquinoline alkaloids: experimental and DFT study

J 2008

Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study

TOUŠEK, Jaromír, Sabine VAN MIERT, Luc PIETERS, Gitte VAN BAELEN, Steven HOSTYN et. al.

Základní údaje

Originální název

Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study

Název česky

Structural and solvent effects on the 13C and 15N NMR chemical shifts of indoloquinoline alkaloids: experimental and DFT study

Autoři

TOUŠEK, Jaromír (203 Česká republika, domácí), Sabine VAN MIERT (56 Belgie), Luc PIETERS (56 Belgie), Gitte VAN BAELEN (56 Belgie), Steven HOSTYN (56 Belgie), Bert U.W. MAES (56 Belgie), Guy LEMIERE (56 Belgie), Roger DOMMISSE (56 Belgie) a Radek MAREK (203 Česká republika, garant, domácí)

Vydání

Magnetic Resonance in Chemistry, John Wiley & Sons, 2008, 0749-1581

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

DOI: 10.1002/mrc.2125

Impakt faktor

Impact factor: 1.443

Kód RIV

RIV/00216224:14310/08:00025717

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1002/mrc.2125

UT WoS

000253559900007

Klíčová slova anglicky

NMR; 1H; 13C; 15N; quantum-chemical calculations; solvent effects; indoloquinoline alkaloids; cryptolepine

Štítky

13C, 15N, 1H, cryptolepine, indoloquinoline alkaloids, NMR, quantum-chemical calculations, solvent effects

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 6. 2013 14:49, prof. RNDr. Radek Marek, Ph.D.

Anotace

ORIG CZ

V originále

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.

Česky

NMR chemické posuny indolochinolinových alkaloidů byly studovány v závislosti na struktuře a prostředí pomocí experimentální NMR spektroskopie a DFT výpočtů.

Návaznosti

LC06030, projekt VaV

Název: Biomolekulární centrum

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Biomolekulární centrum

MSM0021622413, záměr

Název: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Proteiny v metabolismu a při interakci organismů s prostředím

Přiložené soubory

MRC08_46_42.pdf

Požádat o autorskou verzi souboru

Citovat

TOUŠEK, Jaromír, Sabine VAN MIERT, Luc PIETERS, Gitte VAN BAELEN, Steven HOSTYN, Bert U.W. MAES, Guy LEMIERE, Roger DOMMISSE a 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, roč. 46, č. 1, s. 42-51. ISSN 0749-1581. Dostupné z: https://dx.doi.org/10.1002/mrc.2125.

@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 a 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, roč.~46, č.~1, s.~42-51. ISSN~0749-1581. Dostupné z: https://dx.doi.org/10.1002/mrc.2125.

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