Toward tunable amphiphilic copolymers via CuAAC click chemistry of oligocaprolactones onto starch backbone

Uliniuc, Ancuta; Popa, Marcel; Drockenmuller, Éric; Boisson, Fernande; Léonard, Didier; Hamaide, Thierry

doi:10.1016/j.carbpol.2013.03.047

Cited by 26 publications

(12 citation statements)

References 62 publications

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“…However, the signals of the oxyallyl group in 1a were replaced by those of an oxypropargyl group in 1b , most notably a doublet at δ H 2.48 (d, J = 2.4)/75.7 characteristic of the methine proton H-3‴ of a propargyl group. In the 13 C spectrum, C-1‴ and C-2‴ appeared at 55.9 and 78.4 ppm, respectively, in accordance with literature data [ 32 , 33 ]. The location of this substituent at C-4″ was confirmed by the analysis of the HMBC spectrum of 1b on which clear correlations were observed between H-1‴ at δ H 4.66 ppm and C-4″ at δ C 157.5 ppm ( Figure 2 ).…”

Section: Resultssupporting

confidence: 90%

Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum

et al. 2020

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Fusarium is one of the most toxigenic phytopathogens causing diseases and reduced agricultural productivity worldwide. Current chemical fungicides exhibit toxicity against non-target organisms, triggering negative environmental impact, and are a danger to consumers. In order to explore the chemical diversity of plants for potential antifungal applications, crude extract and fractions from Monotes kerstingii were screened for their activity against two multi-resistant Fusarium oxysporum strains: Fo32931 and Fo4287. Antifungal activity was evaluated by the determination of minimum inhibitory concentration (MIC) by broth dilution of fermentative yeasts using kinetic OD600 nm reading by a spectrophotometer. The n-butanol fraction showed the best activity against Fo4287. We screened eleven previously reported natural compounds isolated from different fractions, and a stilbene–coumarin 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-3-methyl-2H-1-benzopyran-2-one (1) was the most active compound against both strains. Compound 1 was employed as a nucleophile with a selection of electrophilic derivatizing agents to synthesize five novel stilbene–coumarin analogues. These semisynthetic derivatives showed moderate activity against Fo32931 with only prenylated derivative exhibiting activity comparable to the natural stilbene–coumarin (1), demonstrating the key role of the phenolic group.

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Section: Resultssupporting

confidence: 90%

Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum

et al. 2020

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“…After the first step of modification, the C 1s spectrum ( Fig. 4b) clearly shows increase of C-(C-H) peak ratio from 30.45% to 43.21% and decrease of other peaks ( Table 2) due to the grafting of CH 2 C CH moiety [47]. This evidence made it possible to go to next step of CA nanofibers functionalization.…”

Section: Structural Surface Characterization Of Nanofibersmentioning

confidence: 83%

“…It was observed that, C 1s and O 1s are two intensive elements as the main compositions of nanofibers. For un-modified CA nanofibers, the ratio of C 1s:O 1s is 62.77:37.23 (%), whereas for CA-propargyl, the intensity of C 1s increase (C 1s:O 1s is 71.21:28.79 (%)) due to contribution of CH 2 C CH group in the first step of modification [47]. After "click" reaction, N 1s was also recorded as one of the component which indicates the successful formation of trizole ring between CA nanofiber surface and CD molecules [48].…”

Section: Structural Surface Characterization Of Nanofibersmentioning

confidence: 98%

Cyclodextrin-grafted electrospun cellulose acetate nanofibers via “Click” reaction for removal of phenanthrene

Çelebioğlu

Demirci

Uyar

2014

Applied Surface Science

119

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a b s t r a c tBeta-cyclodextrin (␤-CD) functionalized cellulose acetate (CA) nanofibers have been successfully prepared by combining electrospinning and "click" reaction. Initially, ␤-CD and electrospun CA nanofibers were modified so as to be azide-␤-CD and propargyl-terminated CA nanofibers, respectively. Then, "click" reaction was performed between modified CD molecules and CA nanofibers to obtain permanent grafting of CDs onto nanofibers surface. It was observed from the SEM image that, while CA nanofibers have smooth surface, there were some irregularities and roughness at nanofibers morphology after the modification. Yet, the fibrous structure was still protected. ATR-FTIR and XPS revealed that, CD molecules were successfully grafted onto surface of CA nanofibers. The adsorption capacity of ␤-CD-functionalized CA (CA-CD) nanofibers was also determined by removing phenanthrene (polycyclic aromatic hydrocarbons, PAH) from its aqueous solution. Our results indicate that CA-CD nanofibers have potential to be used as molecular filters for the purpose of water purification and waste water treatment by integrating the high surface area of nanofibers with inclusion complexation property of CD molecules.

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“…A new characteristic peak at 51.69 ppm appears compared with the spectrum of starch, which is assigned to the carbon of C6-N 3 (Zhang & Edgar, 2015). After CuAAC reaction, the 1,2,3-triazole linkers are clearly observed at 144.58-148.01 and 123.32-124.45 ppm as new peaks in the 13 C NMR spectra of starch derivatives (Uliniuc et al, 2013), and other new signals for the rest of methylenes are appeared below 65 ppm. 13 C NMR spectra of 1,2,3-triazolium-functionalized starch derivatives also corroborate the alkylation since signals corresponding to 1,2,3-triazolium carbons at 142.…”

Section: C Nmr Analysismentioning

confidence: 91%

“…Uliniuc et al (2013) reported that the polycaprolactone-grafted starch copolymers obtained by click chemistry were able to form micelles in an aqueous solution and had potential to be used in controlled drug delivery and cosmetics. The antibacterial-starch biomaterials could be obtained by anchoring the strong electron-withdrawing groups onto the starch backbone by the CuAAC reaction .…”

Section: Introductionmentioning

confidence: 99%

Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property

Tan

Dong

et al. 2017

Carbohydrate Polymers

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Toward tunable amphiphilic copolymers via CuAAC click chemistry of oligocaprolactones onto starch backbone

Cited by 26 publications

References 62 publications

Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum

Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum

Cyclodextrin-grafted electrospun cellulose acetate nanofibers via “Click” reaction for removal of phenanthrene

Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property

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