New Biocompatible Polyesters Derived from α-Amino Acids: Hydrolytic Degradation Behavior

Cohen-Arazi, Naomi; Domb, Abraham J.; Katzhendler, Jehoshua

doi:10.3390/polym2040418

Cited by 19 publications

(14 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The polyesters prepared by direct condensation in bulk (Scheme ) with PTSA as a catalyst resulted in a molecular weight about 2000. The characterization of the derived polymers was previously described …”

Section: Resultsmentioning

confidence: 99%

“…The hydroxy acids derived from L ‐isoleucine, L ‐ and D ‐leucine, L‐ and D ‐phenylalanine, and L ‐ and D‐ valine were prepared by a chemical diazotization method described in the previously published work . The hydroxy acids were characterized by 1 H NMR (DMSO‐ d 6 ), melting point, elemental analysis, and optical activity …”

Section: Methodsmentioning

confidence: 99%

“…Direct condensation of hydroxy acids was carried out in bulk as previously described . The derived polymers were characterized by 1 H NMR, IR, GPC, optical activity, and solubility in several solvents …”

Section: Methodsmentioning

confidence: 99%

“…[34,49,50] The derived polymers were characterized by 1 H NMR, IR, GPC, optical activity, and solubility in several solvents. [46,48]…”

Section: Polymerization Of the A-hydroxy Acids By Direct Condensationmentioning

confidence: 99%

See 3 more Smart Citations

Poly(α‐hydroxy alkanoic acid)s Derived From α‐Amino Acids

Cohen-Arazi

Domb

Katzhendler

2013

Macromolecular Bioscience

Self Cite

View full text Add to dashboard Cite

Biodegradable polyesters derived from hydrophobic amino acids are synthesized by various techniques, resulting in a wide range of molecular weights. The polymers are prepared via a) direct condensation with p-toluenesulfonic acid (PTSA) as catalyst, b) ring-opening polymerization (ROP) of O-carboxyanhydrides, and c) ROP of cyclic dilactones. The polymers obtained by the first method reach a molecular weight ranging from 1000 to 3000 Da, whereas those formed by the second and third method yield extended molecular weights of 15000-30000 Da. The purity of the monomers as well as their steric bulkiness are key factors affecting the polymerizability of cyclic monomers by ROP. Other parameters such as spatial ring alignment and proximity organization may also play a role.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…[34,49,50] The derived polymers were characterized by 1 H NMR, IR, GPC, optical activity, and solubility in several solvents. [46,48]…”

Section: Polymerization Of the A-hydroxy Acids By Direct Condensationmentioning

confidence: 99%

See 2 more Smart Citations

Poly(α‐hydroxy alkanoic acid)s Derived From α‐Amino Acids

Cohen-Arazi

Domb

Katzhendler

2013

Macromolecular Bioscience

Self Cite

View full text Add to dashboard Cite

show abstract

“…One is direct polycondensation of α-hydroxy acids. 9 The molecular weights (MWs) of the resulting PAHAs are generally low as a result of the cyclization side reaction, which hinders the growth of the polymer chain. Furthermore, long reaction times and high temperatures are usually required for the polymer synthesis, leading to various undesired side reactions.…”

Section: Progress In Synthesizing Functional Pahasmentioning

confidence: 99%

Synthesis and Biomedical Applications of Functional Poly(α-hydroxy acids) via Ring-Opening Polymerization of O-Carboxyanhydrides

Yin

Wang

et al. 2015

Acc. Chem. Res.

View full text Add to dashboard Cite

Poly(α-hydroxy acids) (PAHAs) are a class of biodegradable and biocompatible polymers that are widely used in numerous applications. One drawback of these conventional polymers, however, is their lack of side-chain functionalities, which makes it difficult to conjugate active moieties to PAHA or to fine-tune the physical and chemical properties of PAHA-derived materials through side-chain modifications. Thus, extensive efforts have been devoted to the development of methodology that allows facile preparation of PAHAs with controlled molecular weights and a variety of functionalities for widespread utilities. However, it is highly challenging to introduce functional groups into conventional PAHAs derived from ring-opening polymerization (ROP) of lactides and glycolides to yield functional PAHAs with favorable properties, such as tunable hydrophilicity/hydrophobicity, facile postpolymerization modification, and well-defined physicochemical properties. Amino acids are excellent resources for functional polymers because of their low cost, availability, and structural as well as stereochemical diversity. Nevertheless, the synthesis of functional PAHAs using amino acids as building blocks has been rarely reported because of the difficulty of preparing large-scale monomers and poor yields during the synthesis. The synthesis of functionalized PAHAs from O-carboxyanhydrides (OCAs), a class of five-membered cyclic anhydrides derived from amino acids, has proven to be one of the most promising strategies and has thus attracted tremendous interest recently. In this Account, we highlight the recent progress in our group on the synthesis of functional PAHAs via ROP of OCAs and their self-assembly and biomedical applications. New synthetic methodologies that allow the facile preparation of PAHAs with controlled molecular weights and various functionalities through ROP of OCAs are reviewed and evaluated. The in vivo stability, side-chain functionalities, and/or trigger responsiveness of several functional PAHAs are evaluated. Their biomedical applications in drug and gene delivery are also discussed. The ready availability of starting materials from renewable resources and the facile postmodification strategies such as azide-alkyne cycloaddition and the thiol-yne "click" reaction have enabled the production of a multitude of PAHAs with controlled molecular weights, narrow polydispersity, high terminal group fidelities, and structural diversities that are amenable for self-assembly and bioapplications. We anticipate that this new generation of PAHAs and their self-assembled nanosystems as biomaterials will open up exciting new opportunities and have widespread utilities for biological applications.

show abstract

Regioselektive Ringöffnungspolymerisation einer Polyhydroxycarbonsäure zu einem nanoskaligen Trägermaterial mit pH‐abhängiger Stabilität und verzögerter Wirkstofffreisetzung

et al. 2015

View full text Add to dashboard Cite

Synthetische Polyester sind aus Monohydroxycarbonsäuren aufgebaut, um das Problem der Regioselektivität der Veresterung bei der Ringçffnungspolymerisation zu vermeiden. Im Unterschied dazu trägt der lineare Polyester BICpoly gleich vier sekundäre OH-Gruppen pro Monomer und ist trotzdem nur über eine davon regioselektiv verestert. Sowohl bei der Synthese des tricyclischen Monomers als auchb ei der Ringçffnungspolymerisation wird auf Schutzgruppen verzichtet, was BICpoly zu einem attraktiven neuen biokompatiblen Polymer macht.B ICpoly-Nanopartikel kçnnen mit niedermolekularen Wirkstoffen beladen werden oder lassen sich aucha ls dünne Filme auf Oberflächen abscheiden. Die Freisetzung immobilisierter Substanzen macht BICpoly zu einem attraktiven Depot zur Wirkstofffreisetzung, wie wir anhand der Beladung von BICpoly mit Farbstoffen oder dem Zytostatikum Doxorubicin zeigen. Die charakteristische pH-Abhän-gigkeit des Abbausu nterscheidet BICpoly von anderen bekannten Polymeren.

show abstract

New Biocompatible Polyesters Derived from α-Amino Acids: Hydrolytic Degradation Behavior

Cited by 19 publications

References 34 publications

Poly(α‐hydroxy alkanoic acid)s Derived From α‐Amino Acids

Poly(α‐hydroxy alkanoic acid)s Derived From α‐Amino Acids

Synthesis and Biomedical Applications of Functional Poly(α-hydroxy acids) via Ring-Opening Polymerization of O-Carboxyanhydrides

Regioselektive Ringöffnungspolymerisation einer Polyhydroxycarbonsäure zu einem nanoskaligen Trägermaterial mit pH‐abhängiger Stabilität und verzögerter Wirkstofffreisetzung

Contact Info

Product

Resources

About