Recent syntheses and biological activity of lentiginosine and its analogues.

Abstract

(+)-Lentiginosine, a natural trans-1,2-dihydroxyindolizidine belonging to the class of iminosugars, is a potent inhibitor of amyloglucosidase, and a good inhibitor of Hsp90. The non-natural enantiomer, (-)-lentiginosine, induces apoptosis on tumor cells of different origin and is poorly cytotoxic towards non-transformed cells. The significant biological activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This review is an update of a previous survey and summarizes the most recent achievements on biological studies as well as total syntheses of lentiginosine and trans-1,2-dihydroxyindolizidine analogues.

• Authors: Franca M Cordero, Donatella Giomi, Alberto Brandi
• Journal: Current topics in medicinal chemistry (Curr Top Med Chem) Vol. 14 Issue 10 Pg. 1294-307 ( 2014) ISSN: 1873-4294 [Electronic] United Arab Emirates
• PMID: 24758428 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Review)

Chemical References

• Alkaloids
• Antineoplastic Agents
• Enzyme Inhibitors
• HSP90 Heat-Shock Proteins
• lentiginosine
• Glucan 1,4-alpha-Glucosidase

Topics

• Alkaloids (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Proliferation (drug effects)
• Drug Screening Assays, Antitumor
• Enzyme Inhibitors (chemical synthesis, chemistry, pharmacology)
• Glucan 1,4-alpha-Glucosidase (antagonists & inhibitors, metabolism)
• HSP90 Heat-Shock Proteins (antagonists & inhibitors)
• Humans
• Molecular Conformation
• Structure-Activity Relationship