Synthesis of the New 7<i>S</i>‐Aminolentiginosine and Derivatives

Cordero, Franca M.; Bonanno, Paola; Neudeck, Sven; Vurchio, Carolina; Brandi, Alberto

doi:10.1002/adsc.200800806

Cited by 14 publications

(6 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a first step, we evaluated of the ability of compound 1 to interact with Hsp90 by a surface plasmon resonance (SPR) based binding assay; some lentiginosine synthetic derivatives [20] , [21] including the enantiomer (−)-lentiginosine (compounds 2–7 , Figure 1 ), were also tested. Radicicol [22] was used as positive controls.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Natural Iminosugar (+)-Lentiginosine Inhibits ATPase and Chaperone Activity of Hsp90

et al. 2012

Self Cite

View full text Add to dashboard Cite

Heat shock protein 90 (Hsp90) is a significant target in the development of rational cancer therapy due to its role at the crossroads of multiple signaling pathways associated with cell proliferation and cell viability. The relevance of Hsp90 as a therapeutic target for numerous diseases states has prompted the identification and optimization of novel Hsp90 inhibitors as an emerging therapeutic strategy. We performed a screening aimed to identify novel Hsp90 inhibitors among several natural compounds and we focused on the iminosugar (+)-lentiginosine, a natural amyloglucosidases inhibitor, for its peculiar bioactivity profile. Characterization of Hsp90 inhibition was performed using a panel of chemical and biological approaches, including limited proteolysis, biochemical and cellular assays. Our result suggested that the middle domain of Hsp90, as opposed to its ATP-binding pocket, is a promising binding site for new classes of Hsp90 inhibitors with multi-target anti-cancer potential.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Compounds 1–7 were synthesized according to the literature [20] , [21] . Solvents (HPLC grade) were purchased from Romil (ROMIL Ltd, Cambridge, UK).…”

Section: Methodsmentioning

confidence: 99%

Natural Iminosugar (+)-Lentiginosine Inhibits ATPase and Chaperone Activity of Hsp90

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…79a,c However, in some instances, the protecting group could be preserved. 80 For hydrogenation of a range of olefins, it could be shown that the reaction with a catalyst and a reducing agent was not merely a tandem dehydrogenation of ammonia-borane/ hydrogenation of olefin reaction but a true transfer hydrogenation, where the hydrogen does not dissociate from the metal center. It was observed that the reaction went to completion regardless of whether the system was open or closed.…”

Section: Amine-and Phosphine-borane Adducts As Reducing Agentsmentioning

confidence: 99%

Amine− and Phosphine−Borane Adducts: New Interest in Old Molecules

et al. 2010

View full text Add to dashboard Cite

“…It was possible to scale up the reaction to obtain 10 g of nitrone without detriment of yield or optical purity. This nitrone was used by our research group for the synthesis of the putative structure of stemonidine, and this methodology has recently been applied by another research group in the synthesis of an enantiopure nitrone from the corresponding pyrrolidine …”

mentioning

confidence: 99%