Synthesis and ROMP of new sulfobetaine and carboxybetaine norbornene

Pineda-Contreras, Armando; Hernández-Madrigal, Julia V.; Vázquez‐Vuelvas, Oscar F.; Fomine, Serguei

doi:10.1515/epoly-2015-0266

Cited by 3 publications

(6 citation statements)

References 24 publications

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“…To this end, pyridine derivatives containing disulfide moiety were chosen as the starting materials because the tertiary amine residue in pyridine derivatives can induce a nucleophilic ring-opening attack on 1,3-propane sultone to form zwitterionic sulfobetaine groups (Scheme ). Moreover, the disulfide residue is known to be strongly bound to the gold surface, but does not take part in the ring-opening reaction as a nucleophile species . In order to find out which is the better molecular structure for pyridine disulfide derivatives, the reaction of PS with p -DPDS and o -DPDS was monitored by measuring the consumption of pyridine disulfide derivatives by UV–vis spectrophotometry.…”

Section: Resultsmentioning

confidence: 99%

“…PS was dissolved in 2 mL of acetonitrile to form a 2 M solution and p -DPDS, which was dissolved in 3 mL of acetonitrile (0.33 M), was slowly added through a dropping funnel to this solution. The reaction was allowed to proceed for 72 h until yellowish precipitates covered the whole wall of the reaction vial . The precipitate was washed with an excess of acetone to remove residual reactants.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction yield was ∼72%. 1 H NMR (D 2 O) δ = 8.7–8.8 (d, 2H, pyridyl), 8.1–8.2 (d, 2H, pyridyl), 4.7 (t, 2H, N + CH 2 CH 2 ), 2.9–3.0 (t, 2H, CH 2 CH 2 CH 2 ), 2.4 (m, 2H, CH 2 CH 2 S) …”

Section: Methodsmentioning

confidence: 99%

“…The reaction was allowed to proceed for 72 h until yellowish precipitates covered the whole wall of the reaction vial. 21 The precipitate was washed with an excess of acetone to remove residual reactants. The structure of p-DPDSPS was characterized by 1 21 UV−Visible (UV−vis) Monitoring of the Reaction of PS with p-DPDS and o-DPDS.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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One-Pot Synthesis of a Zwitterionic Small Molecule Bearing Disulfide Moiety for Antibiofouling Macro- and Nanoscale Gold Surfaces

Lee

Park

et al. 2018

Langmuir

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The goal of this study is to develop a simple one-pot method for the synthesis of a zwitterionic small molecule bearing disulfide moiety, which can effectively inhibit nonspecific protein adsorption on macroscopic and nanoscopic gold surfaces. To this end, the optimal molecular structure of a pyridine disulfide derivative was explored and a zwitterionic small molecule was successfully synthesized from the tertiary amine residue on the pyridine ring through a one-pot method. The coating conditions of the synthesized zwitterionic molecules on the gold surface were optimized through contact angle measurements, and the strong interactions between the gold surface and the disulfide moiety of the zwitterion small molecule were confirmed by surface plasmon resonance (SPR) analysis and X-ray photoelectron spectroscopy. The antibiofouling properties of the coated gold surface were analyzed by fluorescence microscopic observations after contacting with FITC-labeled bovine serum albumin (BSA) and SPR sensor as contacting with BSA solution. In addition, the effect of zwitterion-coating on the salt stability of and protein adsorption on nanoscopic gold surfaces were examined through a NaCl stability test and BSA adsorption test, respectively. From the obtained results, it was confirmed that the simply synthesized zwitterionic small molecule was effective in inhibiting nonspecific protein adsorption on macroscopic and nanoscopic gold surfaces; further, it enhanced the salt stability of gold nanoparticle surfaces.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

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One-Pot Synthesis of a Zwitterionic Small Molecule Bearing Disulfide Moiety for Antibiofouling Macro- and Nanoscale Gold Surfaces

Lee

Park

et al. 2018

Langmuir

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“…The term polymers carrying betaine units (PB), or polyzwitterions, refers to polymers containing both negative (carboxylate group, sulfonate group or phosphonate/phosphate/phosphinate group) and positive ( onium group without hydrogen atoms) charges located in the same repeat unit and separated by an alkylene group [ 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

New Grafted Copolymers Carrying Betaine Units Based on Gellan and N-Vinylimidazole as Precursors for Design of Drug Delivery Systems

Racoviţă¹,

Baranov

Macsim³

et al. 2020

Molecules

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New grafted copolymers possessing structural units of 1-vinyl-3-(1-carboxymethyl) imidazolium betaine were obtained by graft copolymerization of N-vinylimidazole onto gellan gum followed by the polymer-analogous reactions on grafted polymer with the highest grafting percentage using sodium chloroacetate as the betainization agent. The grafted copolymers were prepared using ammonium persulfate/N,N,N′,N′ tetramethylethylenediamine in a nitrogen atmosphere. The grafting reaction conditions were optimized by changing one of the following reaction parameters: initiator concentration, monomer concentration, polymer concentration, reaction time or temperature, while the other parameters remained constant. The highest grafting yield was obtained under the following reaction conditions: ci = 0.08 mol/L, cm = 0.8 mol/L, cp = 8 g/L, tr = 4 h and T = 50 °C. The kinetics of the graft copolymerization of N-vinylimidazole onto gellan was discussed and a suitable reaction mechanism was proposed. The evidence of the grafting reaction was confirmed through FTIR spectroscopy, X-ray diffraction, 1H-NMR spectroscopy and scanning electron microscopy. The grafted copolymer with betaine structure was obtained by a nucleophilic substitution reaction where the betainization agent was sodium chloroacetate. Preliminary results prove the ability of the grafted copolymers to bind amphoteric drugs (cefotaxime) and, therefore, the possibility of developing the new sustained drug release systems.

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The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2016

Herndon

2018

Coordination Chemistry Reviews

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Synthesis and ROMP of new sulfobetaine and carboxybetaine norbornene

Cited by 3 publications

References 24 publications

One-Pot Synthesis of a Zwitterionic Small Molecule Bearing Disulfide Moiety for Antibiofouling Macro- and Nanoscale Gold Surfaces

One-Pot Synthesis of a Zwitterionic Small Molecule Bearing Disulfide Moiety for Antibiofouling Macro- and Nanoscale Gold Surfaces

New Grafted Copolymers Carrying Betaine Units Based on Gellan and N-Vinylimidazole as Precursors for Design of Drug Delivery Systems

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2016

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