NMR determination of pKa values of indoloquinoline alkaloids

J 2009

NMR determination of pKa values of indoloquinoline alkaloids

GRYCOVÁ, Lenka, Roger DOMMISSE, Luc PIETERS and Radek MAREK

Basic information

Original name

NMR determination of pKa values of indoloquinoline alkaloids

Name in Czech

Stanovení pKa hodnot indolochinolinových alkaloidů pomocí NMR spektroskopie

Authors

GRYCOVÁ, Lenka (203 Czech Republic, belonging to the institution), Roger DOMMISSE (56 Belgium), Luc PIETERS (56 Belgium) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution)

Edition

Magnetic Resonance in Chemistry, John Wiley & Sons, 2009, 0749-1581

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

DOI: 10.1002/mrc.2494

Impact factor

Impact factor: 1.612

RIV identification code

RIV/00216224:14310/09:00036368

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/mrc.2494

UT WoS

000271123300010

Keywords in English

1H NMR;chemical shift;cryptolepine;isocryptolepine;neocryptolepine;isoneocryptolepine;malaria;pH;determination of pKa

Abstract

ORIG CZ

V originále

Malaria is one of the most serious global health problems. Isolating new therapeutic agents with potential antimalarial activity from natural sources or preparing such agents either semisynthetically or synthetically is one strategy for solving the problem of resistance constantly evolving to the drugs currently in use. For alkaloids, the acid-base dissociation constant, pKa, is an important characteristic, thought to be associated with biological activity. In this contribution, pKa values for several indoloquinoline alkaloids were determined by using 1H NMR spectroscopy in a mixture of solvents. The data were recalculated for water solutions using the correction factors reported previously. The structural dependence of the pKa values for cryptolepine and its isomers neocryptolepine, isocryptolepine and isoneocryptolepine as well as some substituted neocryptolepine derivatives is discussed.

In Czech

pKa hodnoty některých indolochinolinových alkaloidů byly stanoveny pomocí 1H NMR spektroskopie.

Links

LC06030, research and development project

Name: 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

Files attached

MRC09_47_977.pdf

Request the author's version of the file

Citovat

GRYCOVÁ, Lenka, Roger DOMMISSE, Luc PIETERS and Radek MAREK. NMR determination of pKa values of indoloquinoline alkaloids. Magnetic Resonance in Chemistry. John Wiley & Sons, 2009, vol. 47, No 11, p. 977-981. ISSN 0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2494.

@article{841773,
   author = {Grycová, Lenka and Dommisse, Roger and Pieters, Luc and Marek, Radek},
   article_number = {11},
   doi = {http://dx.doi.org/10.1002/mrc.2494},
   keywords = {1H NMR;chemical shift;cryptolepine;isocryptolepine;neocryptolepine;isoneocryptolepine;malaria;pH;determination of pKa},
   language = {eng},
   issn = {0749-1581},
   journal = {Magnetic Resonance in Chemistry},
   title = {NMR determination of pKa values of indoloquinoline alkaloids},
   url = {http://dx.doi.org/10.1002/mrc.2494},
   volume = {47},
   year = {2009}
}

TY  - JOUR
ID  - 841773
AU  - Grycová, Lenka - Dommisse, Roger - Pieters, Luc - Marek, Radek
PY  - 2009
TI  - NMR determination of pKa values of indoloquinoline alkaloids
JF  - Magnetic Resonance in Chemistry
VL  - 47
IS  - 11
SP  - 977-981
EP  - 977-981
PB  - John Wiley & Sons
SN  - 07491581
KW  - 1H NMR;chemical shift;cryptolepine;isocryptolepine;neocryptolepine;isoneocryptolepine;malaria;pH;determination of pKa
UR  - http://dx.doi.org/10.1002/mrc.2494
L2  - http://dx.doi.org/10.1002/mrc.2494
N2  - Malaria is one of the most serious global health problems. Isolating new therapeutic agents with potential antimalarial activity from natural sources or preparing such agents either semisynthetically or synthetically is one strategy for solving the problem of resistance constantly evolving to the drugs currently in use. For alkaloids, the acid-base dissociation constant, pKa, is an important characteristic, thought to be associated with biological activity. In this contribution, pKa values for several indoloquinoline alkaloids were determined by using 1H NMR spectroscopy in a mixture of solvents. The data were recalculated for water solutions using the correction factors reported previously. The structural dependence of the pKa values for cryptolepine and its isomers neocryptolepine, isocryptolepine and isoneocryptolepine as well as some substituted neocryptolepine derivatives is discussed.
ER  -

GRYCOVÁ, Lenka, Roger DOMMISSE, Luc PIETERS and Radek MAREK. NMR determination of pKa values of indoloquinoline alkaloids. \textit{Magnetic Resonance in Chemistry}. John Wiley \&{} Sons, 2009, vol.~47, No~11, p.~977-981. ISSN~0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2494.

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