Versatile side chain modification <i>via</i> isocyanide-based multicomponent reactions: tuning the LCST of poly(2-oxazoline)s

“…The obtained microspheres presented an average diameter of 21.73 ± 12.40 μm. The control of the size distribution of the microparticles is a critical issue since microparticles higher than 100 µm with a broad particle size distribution could provoke embolization afterward parenteral injection . As can be seen from these results, the prepared microparticles are in size range of 1–100 µm, hence they could be potentially useful for subcutaneous and intramuscular administration.…”

Section: Resultsmentioning

confidence: 85%

Paclitaxel‐Loaded PLA/PEG/Magnetite Anticancer and Hyperthermic Agent Prepared From Materials Obtained by the Ugi's Multicomponent Reaction

Icart

Santos

Luztonó

et al. 2018

Macromolecular Symposia

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In this study, Magnetic microspheres formed by Magnetite, Paclitaxel (PCT), poly(lactic acid) (PLA), and poly(ethylene glycol) (PEG) diblock copolymers material, synthesized by the Ugi four‐component condensation reaction (UFCC), are prepared by single emulsion and solvent evaporation procedure. Prepared PCT‐loaded magnetic microspheres (PCTMMS) are characterized by magnetic induction hyperthermia (MIH), SEM, and LDS techniques. Microencapsulation process yielded PCT encapsulation efficiency (Ee) between 70 and 80%, determined by HPLC analysis of the resulting supernatant after the microencapsulation process. A kinetic study of drug release in vitro using HPLC showed a sustained and controlled release of PCT. Also, the presence of an external magnetic field speeds up the kinetic release profile of PCT. Anticancer activity of release medium against intestine cancer cell line (Caco2) is determined using the cell viability assay. PCTMMSs are able to inhibit cancer cell growth and colony formation. The main contribution of these results is to propose a new application for UFCC in the preparation of one anticancer and hyperthermic drug delivery systems (DDS) able to improve the cancer treatment and even the welfare of the patients.

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“…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%

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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Versatile side chain modification via isocyanide-based multicomponent reactions: tuning the LCST of poly(2-oxazoline)s

Abstract: Poly(2-oxazoline)s are receiving large current interest based on their potential use in biomedical applications. Here we report a novel, straightforward route towards functional poly(2-oxazoline)s by Passerini and Ugi reactions.

Cited by 45 publications

References 43 publications

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Paclitaxel‐Loaded PLA/PEG/Magnetite Anticancer and Hyperthermic Agent Prepared From Materials Obtained by the Ugi's Multicomponent Reaction

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

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