Vinyl sulfone functionalized silica: a “ready to use” pre-activated material for immobilization of biomolecules

Ortega‐Muñoz, Mariano; Morales‐Sanfrutos, Julia; Megia‐Fernandez, Alicia; Lopéz-Jaramillo, Javier; Hernández-Matéo, Fernando; Santoyo‐González, Francisco

doi:10.1039/c0jm00720j

Cited by 55 publications

(55 citation statements)

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“…[27] For anchoring the ligands onto the surface of silica, the aza-Michael-type addition of vinyl sulfones to amines was thought to be an optimal and simple methodology if appropriately functionalized silicas are used. Two plausible strategies are depicted in Scheme 1 starting with vinyl sulfone silica (5) [28] and amino functionalized silica (6), [29] easily prepared by silanization of activated commercial silica. Reaction of 5 with amino derivatives 1 and 2 afforded the Si-Lm adsorbents Si-PMA and Si-His, respectively, in high yields.…”

Section: Resultsmentioning

confidence: 99%

“…The Dowex M-4195 resin was purchased from Supelco and subjected to a conditioning treatment. The vinyl sulfone propyl silica gel 5, [28] the aminopropyl silica gel 6, [29] the alkynes 10, [38] 15, [39] 16, [40] 17, [41] 18 [42] and 19, [43] the azides 21, [44] 22, [45] 23, [46] 24, [47] 25, [48] 27, [49] and 28 [50] and the alkyne and azido functionalized silicas [33] used as click scavengers were prepared according to reported procedures in literature. TLCs were performed on Merck Silica Gel 60 F 254 aluminium sheets.…”

Section: Experimental Section Generalmentioning

confidence: 99%

“…Preparation of Silica-Supported Chelating Adsorbent Si-PMA Vinyl sulfone silica 5 [28] (1.0 g) was suspended in THF-2-propanol (1:1, 25 mL). 2-Picolylamine (1) (108 mg, 1.0 mmol) was then added.…”

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confidence: 99%

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Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

et al. 2010

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Novel supported chelating adsorbents bearing diverse multidentate nitrogenated ligands with strong copper(I) affinities are easily prepared in non-magnetic and magnetic variants using silica and silica-coated magnetite nanoparticles as suitable supports and the aza-Michael-type addition of vinyl sulfones as the ligation tool. These adsorbents are versatile materials with applications in the copper-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry where their complexation abilities enable them to act either as heterogeneous click catalysts when used in their complexed form or as copper(I) scavengers when used in their uncomplexed form. In the first instance, they proved to be robust and efficient heterogeneous catalysts to promote click reactions using extremely low doses and showing negligible copper leaching, particularly in the case of the silica-based non-magnetic adsorbents, allowing a simple operational protocol for their rapid and easy removal by filtration or magnetic decantation and showing good recyclability properties. In their uncomplexed form, the non-magnetic chelating adsorbents are very efficient copper scavengers that are able to remove any traces of metal contamination and that can be applied in tandem with any heterogeneous supported copper(I) catalysts or as standalone copper removing system in any click protocol allowing the isolation of metal-free clicked compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Experimental Section Generalmentioning

confidence: 99%

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Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

et al. 2010

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“…However, the authors' group has reported the functionalization of silica with vinyl sulfone (31, Fig. 9) to yield a novel "ready to use" pre-activated material that reacts with biomolecules in mild conditions, preserves the activity of enzymes and can be used as an open support in Proteomics (Morales-Sanfrutos et al, 2010b;Ortega-Munoz et al, 2010). In a recent work (Traverso et al, 2010), the application of this hybrid organic-inorganic material to Proteomics was further validated in a pull down experiment that demonstrated the different affinity of two pea h-type thioredoxins for proteins from a crude extract: thioredoxin h2 interacted with classical antioxidant proteins whereas thioredoxin h1 was able to capture a transcription factor, suggesting a regulatory role.…”

Section: Vinyl Sulfone-based Affinity Chromatography Applicationsmentioning

confidence: 99%

Vinyl Sulfone: A Multi-Purpose Function in Proteomics

Lopéz-Jaramillo¹,

Hernández-Matéo²,

Santoyo‐González³

2012

Integrative Proteomics

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“…The election of the strategy to couple Tmab to ISCOMs is critical to preserve the functionality of the former, and the good reactivity of vinyl sulfone group toward proteins was envisaged as the tool to obtain the bioconjugate. 30,31 From a chemical point of view, the coupling relies on the reactivity of the vinyl sulfone group toward Cys, His, and Lys residues, and the fact that according to UniProtKB/Swiss-Prot release 2016_16, Lys is the eighth most frequent amino acid virtually present in any natural protein makes this approach a general coupling strategy. As already reported by our group, the reaction of protein A with LVS promotes the incorporation of protein A to ISCOMs, and the specific interaction between IgGs and protein A can be exploited to further derivatize the ISCOMs with IgGs that act as targeting agents.…”

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confidence: 99%

Functionalized immunostimulating complexes with protein A via lipid vinyl sulfones to deliver cancer drugs to trastuzumab-resistant HER2-overexpressing breast cancer cells

Rodríguez-Serrano¹,

Mut-Salud²,

Cruz‐Bustos³

et al. 2016

IJN

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Background Around 20%–30% of breast cancers overexpress the proto-oncogene human epidermal growth receptor 2 (HER2), and they are characterized by being very invasive. Therefore, many current studies are focused on testing new therapies against tumors that overexpress this receptor. In particular, there exists major interest in new strategies to fight breast cancer resistant to trastuzumab (Tmab), a humanized antibody that binds specifically to HER2 interfering with its mitogenic signaling. Our team has previously developed immunostimulating complexes (ISCOMs) as nanocapsules functionalized with lipid vinyl sulfones, which can incorporate protein A and bind to G immunoglobulins that makes them very flexible nanocarriers. Methods and results The aim of this in vitro study was to synthesize and evaluate a drug delivery system based on protein A-functionalized ISCOMs to target HER2-overexpressing cells. We describe the preparation of ISCOMs, the loading with the drugs doxorubicin and paclitaxel, the binding of ISCOMs to alkyl vinyl sulfone-protein A, the coupling of Tmab, and the evaluation in both HER2-overexpressing breast cancer cells (HCC1954) and non-overexpressing cells (MCF-7) by flow cytometry and fluorescence microscopy. Results show that the uptake is dependent on the level of overexpression of HER2, and the analysis of the cell viability reveals that targeted drugs are selective toward HCC1954, whereas MCF-7 cells remain unaffected. Conclusion Protein A-functionalized ISCOMs are versatile carriers that can be coupled to antibodies that act as targeting agents to deliver drugs. When coupling to Tmab and loading with paclitaxel or doxorubicin, they become efficient vehicles for the selective delivery of the drug to Tmab-resistant HER2-overexpressing breast cancer cells. These nanoparticles may pave the way for the development of novel therapies for poor prognosis resistant patients.

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Vinyl sulfone functionalized silica: a “ready to use” pre-activated material for immobilization of biomolecules

Cited by 55 publications

References 50 publications

Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

Vinyl Sulfone: A Multi-Purpose Function in Proteomics

Functionalized immunostimulating complexes with protein A via lipid vinyl sulfones to deliver cancer drugs to trastuzumab-resistant HER2-overexpressing breast cancer cells

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