NMR determination of pKa values of indoloquinoline alkaloids

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.

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

• 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.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
• Tags: International impact, Reviewed

Abstract

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.

Abstract (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