Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

Sanhueza, Carlos; Mayato, Carlos; ́n, Rubén P. Machı; Padrón, José M.; Dorta, Rosa L.; Vázquez, Jesús T.

doi:10.1016/j.bmcl.2007.04.060

Cited by 8 publications

(8 citation statements)

References 18 publications

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“…Despite some techniques were developed and many synthetic efforts were made, there is still a demand for green methods in the selective synthesis of 2-hydroxy-glycosides. [11][12][13] For several years, we have been interested in the synthesis of carbohydrate derivatives. In our laboratory, different methods were applied to the synthesis of C-, O-and N-glycosides with promising biological activity as antiproliferative agents or enzymatic inhibitors.…”

Section: Ionic Liquids Phase Transfer Catalysis B-o-glycosides Oxone mentioning

confidence: 99%

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Santiago

Lafuente

Bravo

et al. 2017

Tetrahedron Letters

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Section: Ionic Liquids Phase Transfer Catalysis B-o-glycosides Oxone mentioning

confidence: 99%

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Santiago

Lafuente

Bravo

et al. 2017

Tetrahedron Letters

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“…Various D-Cmannopyranoside derivatives have been synthesized in order to evaluate their biological activity as lectin inhibitors relative to their O-glycoside counterpart [41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57]. C-mannosides have also been prepared and tested as potential glycosidase and glycosyltransferase inhibitors [58][59][60][61][62][63][64], as anti-inflammatory derivatives [65], anti-tumor agents [30,66], and anti-bacterial agents [67,68].…”

Section: Introductionmentioning

confidence: 99%

The synthesis of d-C-mannopyranosides

Choumane¹,

Banchet²,

Probst³

et al. 2010

Comptes Rendus. Chimie

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“…However, no inhibition was observed in the HL-60 and 1A9 mammalian cell lines or the bacterial strains Psa-V 18800 and E.coli DH5a, suggesting that the role of benzose in inhibition is selective to S. cervisiae. Compound 29 showed no activity in ∆pdr1∆pdr3 cells however, literature showed 29 as having an IC50 in the low micromolar range against HeLa (Sanhueza et al 2007).…”

Section: Chemical Genomic Screen Gives Insight To the Biological Role Of Benzosementioning

confidence: 95%

“…Compound 29 was has been reported in the literature to be active against HeLa cell lines (Sanhueza et al 2007), it was decided to synthesise this compound to compare whether the activity can also be found in yeast. The dibromocyclopropane 32 was also synthesised to determine if the activity of 29 was related to the possible mechanism of inhibition.…”

Section: Synthesis Of Cyclopropanated Carbohydrate Derivatives 29 To 33mentioning

confidence: 99%

“…Benzose belongs to a class of cyclopropanated carbohydrates which have been shown to have activity against cancer cell lines (Sanhueza et al 2007). Benzose may bind and inhibit a protein synthesis related protein via one of the proposed mechanisms (section 1.4.2) as indicated by the genomic screen results, and so inhibit growth in ∆pdr1∆pdr3 cells.…”

Section: Chemical Genomic Screen Gives Insight To the Biological Role Of Benzosementioning

confidence: 99%

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Mechanism-based design of bioactive cyclopropanated sugars

Davies¹

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<p>Carbohydrates are important feed stocks in synthesis of natural products and so attract the interest of many organic researchers throughout the world, most notably in the last 10 years. The work described within explores the manipulation of the glucose-derived glucal. The addition of a reactive substituted cyclopropane across the alkene has been employed synthetically for many years, the subsequent ring breaking/expansion has been identified in the lab as slow and needing the support of catalysts. We ask the question, “Will cyclopropanated carbohydrates undergo the slow ring breaking/expansion in the presence of proteins, and are we able to identify which of the two types of mechanisms the reaction is going through?” The cyclopropane will act as a warhead to bind to proteins through Ferrier like rearrangements, resulting in irreversible inhibition. To identify the potential of such compounds, a combination of techniques are used to identify potential pathways, protein targets and reactivity through structure activity relationships. The key steps involved in finding out the potential of cyclopropanated carbohydrates are to determine biological activities through bio-assays, structure activity relationships, selective binding, chemical genetics and chemical proteomics. The bio-assays together with structure activity relationships provides evidence on which chemical mechanism is occurring when the biological target is interacting with the bioactive cyclopropanated carbohydrates. The most active compound, benzose (7), was subjected to chemical genetic analysis to determine the pathways and processes that are involved with the mode of action. The chemical genetic analysis was complimented by chemical proteomics to identify the direct biological target. Analogues of benzose were synthesised by the addition of azide groups to undergo a Huisgen Cyclisation within a cell lysate to facilitate binding to an alkyne-substituted matrix.</p>

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Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

Cited by 8 publications

References 18 publications

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

The synthesis of d-C-mannopyranosides

Mechanism-based design of bioactive cyclopropanated sugars

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