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Structure−Activity Relationship Analysis of Novel Derivatives of Narciclasine (an Amaryllidaceae Isocarbostyril Derivative) as Potential Anticancer Agents

2009/01/26 by Laurent Ingrassia, Florence Lefranc, Janique Dewelle +9 · 1 citation
Chemistry · Pharmacology, Toxicology and Pharmaceutics · Medicine · #Chemical synthesis and alkaloids #Alkaloids: synthesis and pharmacology #Cholinesterase and Neurodegenerative Diseases #Chemistry #Apoptosis #In vivo #Cytotoxicity #In vitro #Cytotoxic T cell #Stereochemistry #Cancer cell #Derivative (finance) #IC50 #Pharmacology #Growth inhibition #Cancer #Biochemistry #Biology

paper · doi:10.1021/jm8013585

openalex publication_date 2009/01/26 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/31

Abstract

Narciclasine (1) is a plant growth regulator that has been previously demonstrated to be proapoptotic to cancer cells at high concentrations (> or = 1 microM). Data generated in the present study show that narciclasine displays potent antitumor effects in apoptosis-resistant as well as in apoptosis-sensitive cancer cells by impairing the organization of the actin cytoskeleton in cancer cells at concentrations that are not cytotoxic (IC(50) values of 30-90 nM). The current study further revealed that any chemical modification to the narciclasine backbone generally led to compounds of variable stability, weaker activity, or even the complete loss of antiproliferative effects in vitro. However, one hemisynthetic derivative of narciclasine, compound 7k, demonstrated by both the intravenous and oral routes higher in vivo antitumor activity in human orthotopic glioma models in mice when compared to narciclasine at nontoxic doses. Narciclasine and compound 7k may therefore be of potential use to combat brain tumors.

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