Stimuli-responsive membrane activity of cyclic-peptide–polymer conjugates

Abstract

Cyclic peptide nanotubes were coupled to poly(oxazoline)s using a cleavable connection. Upon stimuli responsive detachment of the polymer an on-demand membrane activity could be achieved.

A sequential native chemical ligation – thiol-Michael addition strategy for polymer–polymer ligation

“…Based on these findings, it was proposed that sequential NCLthiol-Michael addition could be employed to synthesise 3-arm mikto-arm star terpolymers, using a thioester functional polymer in the NCL step. To this end, an acid-functional PEtOx 37 (PEtOx-COOH, Mn = 3100 g/mol) was synthesised and transformed into its thioester (PEtOx-COSPh; 8). Integration of the aromatic signals from the thiophenyl group at 7.38 ppm in the 1 H NMR against the methylene side-chain signal at 2.32 ppm revealed that 95% of the chains contained the thioester group (Fig.…”

“…α-Methoxy-ω-amino-PEG (mPEG-NH2) was obtained from RAPP Polymere and used as received. ω-carboxylic acid poly(2-ethyl-2-oxazoline) (PEtOx30-COOH) 37 and N-acylated poly(aminoester) based oligomers (oligo(MeOx-alt-AA)nA, oligo(EtOx-alt-AA)nA, oligo(ButOx-alt-AA)nA) 38,39 were synthesised according to literature procedures.…”

Trendbericht: Makromolekulare Chemie

“…Ein cyclisches Peptid-Polymer-Konjugat mit reversibler kovalenter Disulfidbindung und reduktionsinduzierter Membraninteraktion. Reproduziert von Literatur 16) . Lizensiert unter CC-BY Hühnereimodell (ex ovo) hinsichtlich ihrer Toxizität und Blutkompatibilität, wobei sie gute Bioverträglichkeit feststellten.…”

“…Die Polymerhülle lässt sich unter reduktiven Bedingungen gezielt abspalten, was eine In-situ-Membranaktivität auf Abruf verspricht. 16) Rodriguez-Emmenegger und Mitarbeiter untersuchten die Selbstanordnung amphiphiler Janus-Dendrimere in Dendrimersome und deren Interaktion mit E.-coli-Bakterien. Dabei beobachteten sie Endozytose in einem nichtaktivierten Prozess.…”

Pyridyl Disulfide Reaction Chemistry: An Efficient Strategy toward Redox-Responsive Cyclic Peptide–Polymer Conjugates

“…[30][31][32] In addition, the introduction of a responsive linker between the cyclic peptide and polymer would endow these materials with stimuli-responsive proper-ties, offering great potential regarding the application of on demand drug delivery systems and antimicrobial drugs, but has been rarely reported. [33] The pyridyl disulfide reaction chemistry, one of the most widely used conjugation chemistry, has been reported to be highly efficient, orthogonal to other conjugation chemistry, and applicable under mild conditions. In addition, this chemistry offers unique properties.…”