4-Nitrophenyl chloroformate activation of poly-α,β-[N-(2-hydroxyethyl)-d,l- aspartamide] and poly-α,β-[N-(2,3- dihydroxypropyl)-d,l-aspartamide]

Marre, Anne De; Soyez, Heidi; Permentier, Dirk; Schacht, Etienne

doi:10.1016/0032-3861(95)90982-8

Cited by 3 publications

(3 citation statements)

References 21 publications

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“…Grafting biologically active molecules on polymers is an attractive approach in biotechnology. Our strategy to functionalize T24 with a Arg-Gly-Asp (RGD) sequence involved an activation step carried out using 4-nitrophenyl chloroformate (NPC) for a partial conversion of the primary hydroxyl side groups on a T24 polymer chain (Scheme a). After purification, hydrolysis of a small fraction of the activated polymer was performed in order to determine the activation rate.…”

Section: Resultsmentioning

confidence: 99%

“…This process was repeated three times. The degree of activation was determined spectrophotometrically by measuring, at 402 nm (ε = 18400 cm –1 M –1 ) with a UV–visible Cary 100 spectrophotometer (Varian, U.S.A.), the amount of p -nitrophenylate released after reaction with NaOH (2 N) . We used 1 mL of NaOH (2 N) per mg of product.…”

Section: Methodsmentioning

confidence: 99%

“…The degree of activation was determined spectrophotometrically by measuring, at 402 nm (ε = 18400 cm −1 M −1 ) with a UV−visible Cary 100 spectrophotometer (Varian, U.S.A.), the amount of p-nitrophenylate released after reaction with NaOH (2 N). 33 We used 1 mL of NaOH (2 N) per mg of product. The activated T24 was stirred in 75 mL of DMSO at 50 °C during 3 h, and after its solubilization, 120 mg of DFKRG cyclic peptide (American Peptide, U.S.A.), 1.7 mL of triethylamine (SDS, France), and 1.47 g of DMAP (Fluka, Switzerland) were added.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Xyloglucan-Derivatized Films for the Culture of Adherent Cells and Their Thermocontrolled Detachment: A Promising Alternative to Cells Sensitive to Protease Treatment

et al. 2013

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By taking advantage of a natural and abundant polymer as well as a straightforward film formation technique, this paper focuses on the conception and use of a new alternative tool for thermo-controlled cell detachment. Thermoresponsive xyloglucan was produced after partial galactose removal by a 24 h reaction with β-galactosidase. The obtained polymer (T24) was then activated by reaction with 4-nitrophenyl chloroformate (NPC) in order to graft a cyclic peptide presenting an arginine-glycine-aspartic acid (RGD) motif. The effect of RGD grafting on the sol-gel transition temperature of T24 is evaluated by rheological measurements. Solvent-casted films of T24-RGD successfully promoted cell adhesion, proliferation, and thermo-controlled detachment. The presented approach is a new alternative for cells sensitive to the proteolytic treatment routinely used for cell detachment. Because the RGD sequence used herein is widely recognized by different cell types, this protocol may be extended to other cells. Besides, the presented chemical route can be applied to different peptide sequences.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Xyloglucan-Derivatized Films for the Culture of Adherent Cells and Their Thermocontrolled Detachment: A Promising Alternative to Cells Sensitive to Protease Treatment

et al. 2013

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Glycidyl methacrylate derivatization of α,β-poly(N-hydroxyethyl)-dl-aspartamide and α,β-polyasparthydrazide

Giammona

Tomarchio

Pitarresi

et al. 1997

Polymer

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Synthesis of Haptens and Protein Conjugates for the Development of Immunoassays for the Insect Growth Regulator Fenoxycarb

Szurdoki

Székacs

et al. 2001

J. Agric. Food Chem.

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Sensitive and selective enzyme-linked immunosorbent assays (ELISAs) in the immobilized antigen format were developed for fenoxycarb (1), an insect growth regulator (IGR). The parent molecule [ethyl 2-(4-phenoxyphenoxy)ethylcarbamate] was derivatized at several positions to obtain haptens (2-5) that were used to produce protein conjugates and rabbit polyclonal antisera. Amino derivatives of fenoxycarb at the terminal and internal rings (2 and 3, respectively) were linked to carrier proteins by azo coupling. Carboxyalkyl-spacer groups were attached to the ethyl group and the nitrogen atom of the target compound (1) to obtain haptens 4 and 5, respectively. Hapten-homologous ELISAs based on protein conjugates of compounds 2 and 4 determined fenoxycarb in the mid-ppb range (IC(50), 102 and 95 ppb, respectively). A more sensitive hapten-heterologous ELISA (IC(50), 17 ppb; detection limit 0.5 ppb) involved the antiserum raised against a conjugate of hapten 2 and the plate-coating antigen obtained from compound 3. These assays displayed no significant interferences with photodegradation products of fenoxycarb, the IGRs methoprene and pyriproxyfen, and a variety of pesticides including the pyrethroids fenvalerate and cypermethryn, the phenoxyacetic acid herbicide 2,4-D, DDT, and the nitrodiphenyl ether herbicides acifluorfen and fluorodifen.

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4-Nitrophenyl chloroformate activation of poly-α,β-[N-(2-hydroxyethyl)-d,l- aspartamide] and poly-α,β-[N-(2,3- dihydroxypropyl)-d,l-aspartamide]

Cited by 3 publications

References 21 publications

Xyloglucan-Derivatized Films for the Culture of Adherent Cells and Their Thermocontrolled Detachment: A Promising Alternative to Cells Sensitive to Protease Treatment

Xyloglucan-Derivatized Films for the Culture of Adherent Cells and Their Thermocontrolled Detachment: A Promising Alternative to Cells Sensitive to Protease Treatment

Glycidyl methacrylate derivatization of α,β-poly(N-hydroxyethyl)-dl-aspartamide and α,β-polyasparthydrazide

Synthesis of Haptens and Protein Conjugates for the Development of Immunoassays for the Insect Growth Regulator Fenoxycarb

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