Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound

Sabine Van Miert, Steven Hostyn, Bert U W Maes, Kanyanga Cimanga, Reto Brun, Marcel Kaiser, P. Mátyus, Roger Dommisse, Guy Lemière, Arnold Vlietinck, Luc Pieters

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

The antiprotozoal activities of three naturally occurring isomeric indoloquinoline alkaloids, i.e., cryptolepine (1), neocryptolepine (2), and isocryptolepine (3), and two dimeric indoloquinoline alkaloids, cryptoquindoline (6) and biscryptolepine (7), originally obtained from the plant Cryptolepis sanguinolenta, were compared with those of a new synthetic indoloquinoline isomer, isoneocryptolepine (4), and a quaternary derivative, N-methyl-isocryptolepinium iodide (5). The latter compounds showed a high antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum strain K1 (IC50 of 0.23 ± 0.04 and 0.017 ± 0.004 μM, respectively), while the cytotoxicity (L6 cells) was 4.32 ± 0.04 and 12.7 ± 2.0 μM, respectively. Isoneocryptolepine (4) was found to act as an inhibitor of β-hematin formation and as a DNA-intercalating agent.

Original languageEnglish
Pages (from-to)674-677
Number of pages4
JournalJournal of Natural Products
Volume68
Issue number5
DOIs
Publication statusPublished - May 2005

Fingerprint

Lead compounds
antimalarials
Alkaloids
Cryptolepis
Cryptolepis sanguinolenta
alkaloids
methyl iodide
Intercalating Agents
chloroquine
Hemin
Chloroquine
Plasmodium falciparum
Cytotoxicity
Isomers
Inhibitory Concentration 50
isomers
inhibitory concentration 50
cytotoxicity
chemical derivatives
Derivatives

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Van Miert, S., Hostyn, S., Maes, B. U. W., Cimanga, K., Brun, R., Kaiser, M., ... Pieters, L. (2005). Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound. Journal of Natural Products, 68(5), 674-677. https://doi.org/10.1021/np0496284

Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound. / Van Miert, Sabine; Hostyn, Steven; Maes, Bert U W; Cimanga, Kanyanga; Brun, Reto; Kaiser, Marcel; Mátyus, P.; Dommisse, Roger; Lemière, Guy; Vlietinck, Arnold; Pieters, Luc.

In: Journal of Natural Products, Vol. 68, No. 5, 05.2005, p. 674-677.

Research output: Contribution to journalArticle

Van Miert, S, Hostyn, S, Maes, BUW, Cimanga, K, Brun, R, Kaiser, M, Mátyus, P, Dommisse, R, Lemière, G, Vlietinck, A & Pieters, L 2005, 'Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound', Journal of Natural Products, vol. 68, no. 5, pp. 674-677. https://doi.org/10.1021/np0496284
Van Miert, Sabine ; Hostyn, Steven ; Maes, Bert U W ; Cimanga, Kanyanga ; Brun, Reto ; Kaiser, Marcel ; Mátyus, P. ; Dommisse, Roger ; Lemière, Guy ; Vlietinck, Arnold ; Pieters, Luc. / Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound. In: Journal of Natural Products. 2005 ; Vol. 68, No. 5. pp. 674-677.
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