Potentially biocompatible polyacrylamides derived by the Ugi four-component reaction

Sehlinger, Ansgar; Ochsenreither, Katrin; Bartnick, Nikolai; Meier, Michael A. R.

doi:10.1016/j.eurpolymj.2015.01.032

Cited by 18 publications

(14 citation statements)

References 43 publications

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“…P7 , P8 , P9, and P12 have in common the presence of long aliphatic chains, which appear to promote crystallization much more efficiently than other groups such as benzyl ( P4 , P5, and P11 ) or naphthyl ( P6 ). These observations are in sharp contrast to the crystallinity of previously reported small molecules with similar functionalities synthesized via Passerini and Ugi MRCs, and suggest a strong influence of the molar fraction of the end‐groups on their aggregation and crystallization. Indeed, the end‐group molar fraction in P7 , P8 , P9, and P12 varies between 12 and 17 mol%, while that of the polymers that did not show microphase segregation oscillates between 7 and 10 mol%.…”

Section: Resultscontrasting

confidence: 96%

“…Telechelic poly(ethylene‐ co ‐butylene)s (PEBs) containing amide end‐groups were synthesized from carboxylic acid terminated telechelic PEB P1 ( M n = 6.5 kDa; Ð = 1.13, Scheme ), which was obtained by base‐catalyzed ring opening of succinic anhydride with hydroxyl terminated telechelic PEB. The Passerini or Ugi reaction of P1 was performed with well‐established components used in previous studies including aldehydes 1a – 1c , isocyanides 2a – 2c , and amine 3a (Scheme ). In addition, we introduced less common components exhibiting long aliphatic moieties (C 12 –C 22 ) such as lauric aldehyde 1d , isocyanides 2e and 2f , and octadecylamine 3b .…”

Section: Resultsmentioning

confidence: 99%

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Phase Segregation in Supramolecular Polymers Based on Telechelics Synthesized via Multicomponent Reactions

Sehlinger

Bartnick

Gunkel

et al. 2017

Macro Chemistry & Physics

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The properties of supramolecular polymers in the solid state are strongly dependent on the binding strength of the supramolecular motifs used; however, It has been previously shown that the nanostructure of supramolecular polymers plays an equally important role. Supramolecular polymers are commonly synthesized via end‐group functionalization of low‐glass transition telechelics with supramolecular units. In these systems, the binding motifs segregate from the soft telechelic backbone and form a hydrogen bonded crystalline hard phase that provides physical cross‐links. To date, the reported synthetic approaches do not permit the introduction of a wide variety of supramolecular units with low synthetic effort, which would facilitate studying the structure‐property relationships. The use of the Passerini and Ugi multicomponent reactions to synthesize various poly(ethylene‐co‐butylene) telechelics with diverse amide end‐groups is reported. The thermal properties of the supramolecular polymers obtained through their solid‐state assembly are investigated and their nanophase‐segregation is studied, which is dictated by the end‐group volume fraction and the amide–amide hydrogen bonding.

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Section: Resultscontrasting

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Phase Segregation in Supramolecular Polymers Based on Telechelics Synthesized via Multicomponent Reactions

Sehlinger

Bartnick

Gunkel

et al. 2017

Macro Chemistry & Physics

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“…However, for medical applications, it is necessary to evaluate the possibility of sterilizing the biomaterial and determining its biocompatibility (Sehlinger et al, 2015). According to the manufacturer of polyamide (Duraform®), this compound is certified for use "in vivo."…”

Section: Discussionmentioning

confidence: 99%

Experimental acrylonitrile butadiene styrene and polyamide evisceration implant: a rabbit clinical and histopathology study

Júnior

Nassar

Neto

et al. 2016

Arq. Bras. Med. Vet. Zootec.

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The purpose of this study was to evaluate acrylonitrile butadiene styrene (ABS) and polyamide implants in rabbits submitted to evisceration at the macroscopic and microstructure level and to assess clinical response and histopathological changes as well. For the experimental study implants of 12mm diameter were prepared by rapid prototyping, weighed and the outer and inner surfaces evaluated macroscopically and by electron microscopy. In addition, a compression test was performed and ultrastructural damage was then determined. After evisceration of the left eyeball, nine New Zealand rabbits received ABS implants and nine others received polyamide implants. The animals were assessed daily for 15 days after surgery and every seven days until the end of the study (90 days). Histopathological evaluation was performed at 15, 45 and 90 days after surgery. The ABS implants weighed approximately 0.44g, while the polyamide ones weighed 0.61g. Scanning electron microscopy demonstrated that the ABS implants had regular-sized, equidistant micropores, while the polyamide ones showed micropores of various sizes. The force required to fracture the ABS implant was 14.39 ±0.60 Mpa, while for the polyamide one, it was 16.80 ±1.05 Mpa. Fifteen days after surgery, we observed centripetal tissue infiltration and scarce inflammatory infiltrate. Implants may be used in the filling of anophthalmic cavities, because they are inert, biocompatible and allow tissue integration.Keywords: rabbits, ocular prosthesis, polymers RESUMO Avaliou-se a macroscopia, a microestrutura, a resposta clínica e histopatológica de implantes de acrilonitrila butadieno estireno (ABS) e poliamida em coelhos submetidos à evisceração. Para o estudo experimental, os implantes foram elaborados por meio de prototipagem rápida, com 12mm de diâmetro, pesados e tiveram suas superfícies avaliadas macroscopicamente e por microscopia eletrônica de varredura. Adicionalmente, foi realizado ensaio de compressão para determinar a força necessária para fraturar os implantes. Após a evisceração do olho esquerdo, nove coelhos da raça Nova Zelândia receberam implantes de poliamida e nove outros receberam implantes de ABS. Os animais foram avaliados diariamente nos primeiros 15 dias após a cirurgia e a cada sete dias até o fim do período experimental (90 dias

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“…In recent years, the Ugi reaction has been successfully used for the synthesis of structurally diverse polymer . Generally speaking, if we want to obtain polymers in a one‐pot via the Ugi reaction, the four components must contain one AB‐type component or two bifunctional AA‐type components .…”

Section: Ugi Reaction Of Amino Acids For γ‐ δ‐ and Poly(ε‐peptoid)smentioning

confidence: 99%

Polypeptoids synthesis based on Ugi reaction: Advances and perspectives

2019

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Polypeptoids are peptidomimetic polymers invented in the early 1990s. Although polypeptoid chemistry is developing rapidly, the simple synthesis of polypeptoids and sequence‐controlled polypeptoids still remains a challenge. Fortunately, we have seen a drastic rising trend in the area of Ugi reaction for polypeptoid chemistry. In the following article, recent examples of the Ugi reaction for polypeptoids synthesis will be presented, as will their suitability for sequence‐defined peptide‐peptoid hybrids. The advantages and limitations of the Ugi reaction will be discussed, which is important for the simple and general synthesis of polypeptoids.

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Potentially biocompatible polyacrylamides derived by the Ugi four-component reaction

Cited by 18 publications

References 43 publications

Phase Segregation in Supramolecular Polymers Based on Telechelics Synthesized via Multicomponent Reactions

Phase Segregation in Supramolecular Polymers Based on Telechelics Synthesized via Multicomponent Reactions

Experimental acrylonitrile butadiene styrene and polyamide evisceration implant: a rabbit clinical and histopathology study

Polypeptoids synthesis based on Ugi reaction: Advances and perspectives

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