Switchable synthesis of glycosyl selenides or diselenides with direct use of selenium as the selenating agent

Iadonisi, Alfonso; Traboni, Serena; Capasso, Domenica; Bedini, Emiliano; Cuomo, Sabrina; Gaetano, Sonia Di; Vessella, Giulia

doi:10.1039/d1qo00045d

Cited by 11 publications

(12 citation statements)

References 32 publications

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“…The resulting anomeric hemiacetal 6 was acetylated with sodium acetate and acetic anhydride to yield compound 7 as an approximately equimolar anomeric mixture. The key step of the sequence was the synthesis of the diglycosyl selenide, which was performed by adapting a recently developed procedure, applied to date only to peracetylated precursors [ 43 ]. To this aim, compound 7 was first iodinated at the anomeric position with the iodine/silane combined reagent [ 45 , 46 ].…”

Section: Resultsmentioning

confidence: 99%

“…The poor solubility of the organoselenides that reduces their availability can be easily overcome by selenoglycosides [ 39 , 40 ], but the biological assessment of the latter has been limited to date by the need for expensive synthetic procedures. As a matter of fact, poor data are available on the bioactivity of selenoglycosides or 3,3′-substituted selenoglycosides derivatives covered by patent [ 41 ], as essentially are focused only on the assessment of their affinity towards lectin receptors [ 42 ] rather than their biological effect A recently introduced approach provided us with a very useful tool for quick production of digalactosyl selenides starting from a cheap selenenating agent [ 43 ], a method which is herein complemented by the availability of a simple synthetic strategy for the regioselective functionalization of carbohydrates with aromatic groups.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Anticancer Activity of a Selenium-Containing Galectin-3 and Galectin-9N Inhibitor

Gaetano

Pirone

Galdadas

et al. 2022

IJMS

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Galectins are soluble β-D-galactoside-binding proteins whose implication in cancer progression and disease outcome makes them prominent targets for therapeutic intervention. In this frame, the development of small inhibitors that block selectively the activity of galectins represents an important strategy for cancer therapy which is, however, still relatively underdeveloped. To this end, we designed here a rationally and efficiently novel diglycosylated compound, characterized by a selenoglycoside bond and the presence of a lipophilic benzyl group at both saccharide residues. The relatively high binding affinity of the new compound to the carbohydrate recognition domain of two galectins, galectin 3 and galectin 9, its good antiproliferative and anti-migration activity towards melanoma cells, as well as its anti-angiogenesis properties, pave the way for its further development as an anticancer agent.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of a Selenium-Containing Galectin-3 and Galectin-9N Inhibitor

Gaetano

Pirone

Galdadas

et al. 2022

IJMS

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“…After 24 h incubation, cells were treated with increasing concentrations of synthetized compounds previously solubilized in DMSO at 50 mM concentration. Cell proliferation was determined by using (2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazolium, monosodium salt (CCK-8, Sigma Aldrich) for Jurkat cells [ 31 ], and the 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide assay (MTT, Sigma Aldrich, Sigma Aldrich, St. Louis, MO, USA)) for HeLa, WM266, PANC, U87 and HDF cells [ 32 ], after 48 h treatment. Plates were then analyzed by using a microplate reader (Enspire, Perkin Elmer Italia Spa, Milano, Italy) at 450 (CCK-8) or 570 nm (MTT).…”

Section: Methodsmentioning

confidence: 99%

Phosphodiester Silybin Dimers Powerful Radical Scavengers: A Antiproliferative Activity on Different Cancer Cell Lines

et al. 2022

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Silibinin is the main biologically active component of silymarin extract and consists of a mixture 1:1 of two diastereoisomeric flavonolignans, namely silybin A (1a) and silybin B (1b), which we call here silybins. Despite the high interest in the activity of this flavonolignan, there are still few studies that give due attention to the role of its stereochemistry and, there is still today a strong need to investigate in this area. In this regard, here we report a study concerning the radical scavenger ability and the antiproliferative activity on different cell lines, both of silybins and phosphodiester-linked silybin dimers. An efficient synthetic strategy to obtain silybin dimers in an optical pure form (6aa, 6ab and 6bb) starting from a suitable building block of silybin A and silybin B, obtained by us from natural extract silibinin, was proposed. New dimers show strong antioxidant properties, determined through hydroxyl radical (HO●) scavenging ability, comparable to the value reported for known potent antioxidants such as quercetin. A preliminary screening was performed by treating cells with 10 and 50 μM concentrations for 48 h to identify the most sensitive cell lines. The results show that silibinin compounds were active on Jurkat, A375, WM266, and HeLa, but at the tested concentrations, they did not interfere with the growth of PANC, MCF-7, HDF or U87. In particular, both monomers (1a and 1b) and dimers (6aa, 6ab and 6bb) present selective anti-proliferative activity towards leukemia cells in the mid-micromolar range and are poorly active on normal cells. They exhibit different mechanisms of action in fact all the cells treated with the 1a and 1b go completely into apoptosis, whereas only part of the cells treated with 6aa and 6ab were found to be in apoptosis.

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“…Benzoyl-protected anomeric bromide 51 was synthesized from D-mannose using the reported procedure. [19] Compound 51 on treatment with tetraselenotungstate 2 gave two products 52 and 53 (3 : 1) in 84 % yield. While tetraselenide 52 was formed as the major product, compound 53 was also formed as a minor product (19 % yield).…”

Section: Synthesis Of Unusual Selenosugarsmentioning

confidence: 99%

“…[16d] The utility of tetraselenotungstate 2 has been demonstrated in the synthesis of alkyl and aryl diselenides, selenocystine derivatives and also glucose diselenides 5 (Scheme 1). [18,19]…”

Section: Benzyltriethylammonium Tetrathiomolybdate and Tetraethylammonium Tetraselenotungstate [Bnet 3 N] 2 Mos 4 /[Et 4 N]2wsementioning

confidence: 99%

Tetrathiomolybdate and Tetraselenotungstate as Sulfur/Selenium Transfer Reagents: Applications in the Synthesis of New Thio/Seleno Sugars

Kirubakaran

Sureshkumar

Chandrasekaran

2021

The Chemical Record

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Sulfur and selenium containing sugars have gained prominence in the last two decades because of their importance in several biological applications. These type of carbohydrate scaffolds are also challenging targets for synthesis. In this personal note, we have summarised the results of our investigation over the last 20 years on the use of two reagents, benzyltriethylammonium tetrathiomolybdate and tetraethylammonium tetraselenotungstate, in efficient transfer of sulfur and selenium respectively to the synthesis of a number of carbohydrate derivatives.

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Switchable synthesis of glycosyl selenides or diselenides with direct use of selenium as the selenating agent

Abstract: Symmetrical diglycosyl-selenides or diselenides can be readily prepared with high chemoselectivity by direct use of elemen-tary selenium as a cheap selenating agent (reduced in situ by sodium borohydride), and glycosyl...

Cited by 11 publications

References 32 publications

Design, Synthesis, and Anticancer Activity of a Selenium-Containing Galectin-3 and Galectin-9N Inhibitor

Design, Synthesis, and Anticancer Activity of a Selenium-Containing Galectin-3 and Galectin-9N Inhibitor

Phosphodiester Silybin Dimers Powerful Radical Scavengers: A Antiproliferative Activity on Different Cancer Cell Lines

Tetrathiomolybdate and Tetraselenotungstate as Sulfur/Selenium Transfer Reagents: Applications in the Synthesis of New Thio/Seleno Sugars

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