Document Detail

The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine.
MedLine Citation:
PMID:  20053629     Owner:  NLM     Status:  MEDLINE    
D-(-)-Lentiginosine [(-)-4], the nonnatural enantiomer of the iminosugar indolizidine alkaloid L-(+)-lentiginosine, acts as apoptosis inducer on tumor cells of different origin, in contrast to its natural enantiomer. Although D-(-)-4 exhibited a proapoptotic activity towards tumor cells at level lower than the chemotherapeutic agent, SN38, it was less proapoptotic towards normal cells and less cytotoxic. Apoptosis induced by D-(-)-4 was caspase-dependent, as shown by the increased expression and activity of caspase-3 and -8 in treated cells, and by inhibition following treatment with the pan caspase inhibitor, ZVAD-FMK. This study highlighted how a natural iminosugar alkaloid and its synthetic enantiomer, which were simply known for their inhibition against a fungal glucoamylase, could behave in a complete different way when tested towards cell growth and death of cells of different origin.
Beatrice Macchi; Antonella Minutolo; Sandro Grelli; Francesca Cardona; Franca M Cordero; Antonio Mastino; Alberto Brandi
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-01-05
Journal Detail:
Title:  Glycobiology     Volume:  20     ISSN:  1460-2423     ISO Abbreviation:  Glycobiology     Publication Date:  2010 May 
Date Detail:
Created Date:  2010-04-08     Completed Date:  2010-09-09     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9104124     Medline TA:  Glycobiology     Country:  England    
Other Details:
Languages:  eng     Pagination:  500-6     Citation Subset:  IM    
Department of Neuroscience, University of Rome Tor Vergata Via Montpellier 1 Rome 00133 and IRCCS S. Lucia, Via Ardeatina 300 00100 Rome, Italy.
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MeSH Terms
Alkaloids / chemical synthesis,  chemistry,  pharmacology*
Amino Acid Chloromethyl Ketones / pharmacology
Antineoplastic Agents / chemical synthesis,  chemistry,  pharmacology*
Apoptosis / drug effects*
Camptothecin / analogs & derivatives,  pharmacology
Caspase 3 / antagonists & inhibitors,  biosynthesis,  metabolism
Caspase 8 / antagonists & inhibitors,  biosynthesis,  metabolism
Cell Proliferation / drug effects
Cell Survival / drug effects
Cells, Cultured
Dose-Response Relationship, Drug
Drug Evaluation, Preclinical
Enzyme Inhibitors / chemical synthesis,  chemistry,  pharmacology
Glucan 1,4-alpha-Glucosidase / antagonists & inhibitors
Molecular Conformation
Structure-Activity Relationship
Reg. No./Substance:
0/Alkaloids; 0/Amino Acid Chloromethyl Ketones; 0/Antineoplastic Agents; 0/Enzyme Inhibitors; 0/SN38-Glu; 0/benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone; 125279-72-3/lentiginosine; 7689-03-4/Camptothecin; EC 1,4-alpha-Glucosidase; EC 3.4.22.-/Caspase 3; EC 3.4.22.-/Caspase 8

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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