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De Feijter I.,TU Eindhoven | De Feijter I.,Laboratory of Chemical Biology | Goor O.J.G.M.,TU Eindhoven | Goor O.J.G.M.,Laboratory of Chemical Biology | And 14 more authors.
Synlett | Year: 2015

Supramolecular polymers have shown to be powerful scaffolds for tissue engineering applications. Supramolecular biomaterials functionalized with ureidopyrimidinone (UPy) moieties, which dimerize via quadruple hydrogen-bond formation, are eminently suitable for this purpose. The conjugation of the UPy moiety to biologically active peptides ensures adequate integration into the supramolecular UPy polymer matrix. The structural complexity of UPy-peptide conjugates makes their synthesis challenging and until recently low yielding, thus restricted the access to structurally diverse derivatives. Here we report optimization studies of a convergent solid-phase based synthesis of UPy-modified peptides. The peptide moiety is synthesized using standard Fmoc solid-phase synthesis and the UPy fragment is introduced on the solid-phase simplifying the synthesis and purification of the final UPy-peptide conjugate. The convergent nature of the synthesis reduces the number of synthetic steps in the longest linear sequence compared to other synthetic approaches. We demonstrate the utility of the optimized route by synthesizing a diverse range of biologically active UPy-peptide bioconjugates in multimilligram scale for diverse biomaterial applications. 1 Introduction 2 Divergent Synthesis 3 Convergent Synthesis 4 UPy-Amine Strategy 5 UPy-Carboxylic Acid Strategy 6 Conclusion. © Georg Thieme Verlag Stuttgart · New York.

Liu N.,Laboratory of Chemical Biology | Li K.,CAS Changchun Institute of Applied Chemistry | Li X.,Changchun University of Technology | Chang Y.,Laboratory of Chemical Biology | And 9 more authors.
ACS Nano | Year: 2016

Toxicological responses of nanomaterials have been closely correlated to their physicochemical properties, and establishment of a property-activity relationship of nanomaterials is favorable for a deep understanding of the nanomaterials' toxicity mechanism, prospectively predicting nanomaterials' potential hazards and rationally designing safer nanomaterials. Faceted nanomaterials usually exhibit more versatile and effective performance than spherical nanomaterials due to their selectively exposed crystallographic facets with high densities of unsaturated atoms. These facets have high surface reactivity, capable of eliciting strong interactions with biological systems. Few studies paid attention to the toxic behaviors of faceted nanomaterials in terms of their distinctive facets. In the present study, the toxicological role of the crystallographic facets of TiO2 nanomaterials was investigated, and the precise property-activity relationship was exploited to clearly understand the toxicity of faceted nanomaterials. A series of faceted TiO2 nanocrystals with the morphology of truncated octahedral bipyramids were prepared to expose different percentages of {101} and {001} facets on the surface. Density functional theory calculation revealed that {101} facets could only molecularly absorb water molecules while {001} facets due to their surface-unsaturated Ti atoms could dissociate the absorbed water molecules to generate hydroxyl radicals. Biophysical assessments corroborated the increased production of hydroxyl radicals on the {001} facets compared to {101} facets, which endowed {001} facets with strong hemolytic activity and elicited severe toxicities. A series of increased oxidative stress toxicological responses, including cellular ROS production, heme oxygenase-1 expression, cellular GSH depletion, and mitochondrial dysfunctions, were triggered by faceted TiO2 nanocrystals with progressively increased {001} percentages, demonstrating the toxicological roles of {001} facets. © 2016 American Chemical Society.

Zhao Q.,Hangzhou Normal University | Shen C.,Hangzhou Normal University | Zheng H.,Hangzhou Normal University | Zhang J.,Laboratory of Chemical Biology | Zhang P.,Hangzhou Normal University
Carbohydrate Research | Year: 2010

A series of novel glycosyl thiazol-2-imines (3a-g) have been synthesized regioselectively in good yields from the hydrolysis of thiazol-2(3H)-imine-linked glycoconjugates. The glycosyl thiazol-2-imines were evaluated for their antitumor activity against Hela (cervical carcinoma), HCT-8 (colon carcinoma) and Bel-7402 (liver carcinoma). Among the compounds screened, 1-benzoyl-4-(4-nitrophenyl)-3-β-d-glucopyranosyl-thiazol-2(3H)-imine (3c) was found to be the most active compound against HCT-8. Crown Copyright © 2009.

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