Poly(amino acid)s and Ester-Amide Copolymers: Tailor-Made Biodegradable Polymers

Rypáček, František; Dvořák, Michal; Štefko, I.; Machová, Luďka; Škarda, V.; Kubies, Dana

doi:10.1021/bk-2001-0786.ch016

Cited by 7 publications

(10 citation statements)

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“…monomer/initiator ratio, M/I). Frequently used small amines are n-hexylamine and benzylamine [66][67][68][69][70][71] (see reference [49], Chapter 2). The third reason is introduction of functional end groups to the CO chain end of the polypeptides.…”

Section: Stepwise Peptide Synthesesmentioning

confidence: 99%

“…Two different initiation processes were applied to the stepwise (sequential) polymerization of two NCAs. Either amines such as n-propylamine, allylamine, n-hexylamine, and piperidine were used as initiators, [121][122][123][124][125][126][127][128][129] or a metal complex, most frequently [Co(PMe 3 ) 4 ], was used. [89,[102][103][104][105][106][107][108][109] Furthermore, two variants of the sequential copolymerization may be distinguished.…”

Section: Block Copolymersmentioning

confidence: 99%

“…Examples of this synthetic strategy are copolypeptides consisting of a poly(lGlu) block combined with a poly(g-Bzl-l-Glu) block (40). [121,122] In this case, the (l-Glu) block was prepared first by deprotection of a poly(g-Bzl-l-Glu) chain, which was then in turn used as a macroinitiator for the new g-Bzl-l-Glu-NCA. Several diblock copolypeptides based on l-Lys were prepared by combining different substituents of the N e protecting group [123,124] (structures 41 and 42).…”

Section: Block Copolymersmentioning

confidence: 99%

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Polypeptides and 100 Years of Chemistry of α‐Amino Acid N‐Carboxyanhydrides

2006

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Syntheses and polymerizations of alpha-amino acid N-carboxyanhydrides (NCAs) were reported for the first time by Hermann Leuchs in 1906. Since that time, these cyclic and highly reactive amino acid derivatives were used for stepwise peptide syntheses but mainly for the formation of polypeptides by ring-opening polymerizations. This review summarizes the literature after 1985 and reports on new aspects of the polymerization processes, such as the formation of cyclic polypeptides or novel organometal catalysts. Polypeptides with various architectures, such as diblock, triblock, and multiblock sequences, and star-shaped or dendritic structures are also mentioned. Furthermore, lyotropic and thermotropic liquid-crystalline polypeptides will be discussed and the role of polypeptides as drugs or drug carriers are reviewed. Finally, the hypothetical role of NCAs in molecular evolution on the prebiotic Earth is discussed.

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Section: Stepwise Peptide Synthesesmentioning

confidence: 99%

Section: Block Copolymersmentioning

confidence: 99%

Section: Block Copolymersmentioning

confidence: 99%

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Polypeptides and 100 Years of Chemistry of α‐Amino Acid N‐Carboxyanhydrides

2006

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“…Diese Gruppe von Copolymeren wurde nach zwei Gesichtspunkten untergliedert: Erstens wurde die Zahl der Blöcke berück-sichtigt und dementsprechend eine Unterteilung in Diblock-, [121][122][123][124][125][126][127][128][129] oder aber Metallkomplexe, am häufigsten [(PMe 3 ) 4 Co]. [89,[102][103][104][105][106][107][108][109] 40).…”

Section: Blockcopolymereunclassified

Polypeptide und 100 Jahre Chemie der α‐Aminosäure‐N‐carboxyanhydride

Kricheldorf

2006

Angewandte Chemie

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Synthese und Polymerisation von α‐Aminosäure‐N‐carboxyanhydriden (NCAs) wurden erstmals im Jahre 1906 von Herrmann Leuchs beschrieben. Seit dieser Zeit wurden diese cyclischen, sehr reaktiven α‐Aminosäurederivate mehrfach zur schrittweisen Peptidsynthese eingesetzt, sie wurden aber vor allem zur Herstellung von Polypeptiden durch ringöffnende Polymerisation (ROP) verwendet. Es werden nun neue Aspekte der ringöffnenden Polymerisation diskutiert, z. B. die Verwendung neuartiger metallorganischer Initiatoren oder die Entstehung cyclischer Polypeptide. Des Weiteren werden Architekturen wie Diblock‐, Triblock‐ und Multiblockcopolymere sowie sternförmige oder hochverzweigte Polypeptide vorgestellt. Ferner werden lyotrope und thermotrope Polypeptide sowie die Verwendung von Polypeptiden als Pharmaka oder Pharmakaträger besprochen. Schließlich wird die Rolle von NCAs im Konzept der molekularen Evolution diskutiert.

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“…[17][18][19] Its peptide-like structure makes it inherently more biodegradable than carbon chain polymers. [20] Even the highly branched polysuccinimide (PSI) formed from maleic acid and ammonia has proven to be %70% biodegradable. [21] In this study, poly(L-succinimide)-graft-polyethylenimines (PSPs), a class of biodegradable cationic polymers, were prepared by direct one-step aminolysis of PSIs in the presence of branched PEI800 without any catalyst (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Convenient Preparation of Biodegradable PEI‐Containing Polymers as Non‐Viral Vectors for Gene Transfection

Huang

Feng

Nie

et al. 2009

Macromolecular Bioscience

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Poly(L-succinimide)-graft-polyethylenimines (PSPs) were prepared as non-viral vectors for gene transfection. Branched polyethylenimine (Mw= 800, PEI800) was grafted to poly(L-succinimide) (PSI) in a one-step reaction with no catalyst. Gel retardation assay showed that the mobility of PSP/pDNA complexes was completely retarded at the low N/P ratio of 0.42. In vitro transfection experiments showed that, at N/P ratio of 0.84, PSPs can reach the highest transfection level with ten-fold enhancement in 293T cells and five-fold enhancement in HeLa cells as compared with PEI25k (Mw= 25,000). Fluorescent confocal microscopy showed that pGL-3 plasmids condensed by PSPs could be effectively transported into the nuclei of HeLa cells. Significantly reduced cytotoxicity of polymers was observed towards 293T and HeLa cells, with the 50% inhibition concentration of PSPs being almost four times higher than that of PEI25k.

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Poly(amino acid)s and Ester-Amide Copolymers: Tailor-Made Biodegradable Polymers

Cited by 7 publications

References 0 publications

Polypeptides and 100 Years of Chemistry of α‐Amino Acid N‐Carboxyanhydrides

Polypeptides and 100 Years of Chemistry of α‐Amino Acid N‐Carboxyanhydrides

Polypeptide und 100 Jahre Chemie der α‐Aminosäure‐N‐carboxyanhydride

Convenient Preparation of Biodegradable PEI‐Containing Polymers as Non‐Viral Vectors for Gene Transfection

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