Optimized Synthesis of Salicylate-based Poly( anhydride-esters)

Schmeltzer, Robert C.; Anastasiou, Theodore J.; Uhrich, Kathryn E.

doi:10.1007/s00289-003-0123-6

Cited by 66 publications

(99 citation statements)

References 16 publications

(15 reference statements)

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“…[2][3][4][5][6][7][8][9][10][11][12] Only rarely, however, have studies been made on poly(ester-anhydrides) utilizing biodegradable polyesters as precursors for high molecular weight polymer. Slivniak and Domb [13] prepared ABA triblock copolymers composed of sebacic acid polyanhydride with poly(lactic acid) terminals.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Poly(ester‐anhydrides) Based on Different Polyester Precursors

Korhonen

Helminen

Seppälä

2004

Macro Chemistry & Physics

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Summary: Poly(ester‐anhydrides) were synthesised from poly(L‐lactide), poly(D,L‐lactide), and poly(ε‐caprolactone) prepolymers prepared by ring‐opening polymerisation of cyclic esters in the presence of 1,4‐butanediol or ricinoleic acid as co‐initiator. The hydroxyl group end functionality of the prepolymers was converted to carboxylic acid functionality by reaction with succinic anhydride, and the polyester precursors were coupled by melt polycondensation to give poly(ester‐anhydrides). 1,4‐Butanediol was used as co‐initiator to study the properties of poly(ester‐anhydrides) prepared from different monomers, whereas ricinoleic acid was used as co‐initiator to introduce a hydrophobic fatty acid moiety to the polyester precursor. In hydrolysis tests, the poly(ester‐anhydrides) showed a two‐stage degradation comprising a rapid hydrolysis of anhydride linkages within three days, followed by the slower hydrolysis of the remaining polyester oligomer. Weight loss of the poly(ester‐anhydrides) depended most importantly on molecular weight and thermal properties of the polyester precursors; thus, poly(ester‐anhydrides) prepared from low molecular weight prepolymers having thermal transitions below 37 °C showed very fast weight loss.image

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Section: Introductionmentioning

confidence: 99%

Synthesis of Poly(ester‐anhydrides) Based on Different Polyester Precursors

Korhonen

Helminen

Seppälä

2004

Macro Chemistry & Physics

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“…PCL-SAPAE membranes were synthesized according to previously described methods. [29][30][31][32] The FD-SAPAE polymer (poly[1,6-bis(o-carboxyphenoxy) hexanoate]) had an average molecular weight (Mw) of 13,400, polydispersity index (PDI) of 1.7, and a glass transition temperature (Tg) of 46°C (Fig. 1B).…”

Section: Figmentioning

confidence: 99%

Salicylic Acid-Based Polymers for Guided Bone Regeneration Using Bone Morphogenetic Protein-2

Subramanian

Mitchell

et al. 2015

Tissue Engineering Part A

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Bone morphogenetic protein-2 (BMP-2) is used clinically to promote spinal fusion, treat complex tibia fractures, and to promote bone formation in craniomaxillofacial surgery. Excessive bone formation at sites where BMP-2 has been applied is an established complication and one that could be corrected by guided tissue regeneration methods. In this study, anti-inflammatory polymers containing salicylic acid [salicylic acid-based poly(anhydrideester), SAPAE] were electrospun with polycaprolactone (PCL) to create thin flexible matrices for use as guided bone regeneration membranes. SAPAE polymers hydrolyze to release salicylic acid, which is a nonsteroidal anti-inflammatory drug. PCL was used to enhance the mechanical integrity of the matrices. Two different SAPAE-containing membranes were produced and compared: fast-degrading (FD-SAPAE) and slow-degrading (SD-SAPAE) membranes that release salicylic acid at a faster and slower rate, respectively. Rat femur defects were treated with BMP-2 and wrapped with FD-SAPAE, SD-SAPAE, or PCL membrane or were left unwrapped. The effects of different membranes on bone formation within and outside of the femur defects were measured by histomorphometry and microcomputed tomography. Bone formation within the defect was not affected by membrane wrapping at BMP-2 doses of 12 mg or more. In contrast, the FD-SAPAE membrane significantly reduced bone formation outside the defect compared with all other treatments. The rapid release of salicylic acid from the FD-SAPAE membrane suggests that localized salicylic acid treatment during the first few days of BMP-2 treatment can limit ectopic bone formation. The data support development of SAPAE polymer membranes for guided bone regeneration applications as well as barriers to excessive bone formation.

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“…5 In brief, monomers (1 g) were heated to 180°C under high vacuum (Ͻ 2 mm Hg) for 1 to 3 h. During this time, the melt was actively stirred at approximately 100 rpm by an overhead stirrer. Polymerization was considered complete when the viscosity of the melt remained constant and/or the melt solidified.…”

Section: Polymer/copolymer Synthesismentioning

confidence: 99%

Investigation into the erosion mechanism of salicylate‐based poly(anhydride‐esters)

Whitaker-Brothers

Uhrich

2005

J Biomedical Materials Res

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Salicylate-based poly(anhydride-esters), collectively referred to as PolyAspirin, hydrolytically degrade into salicylic acid, a nonsteroidal anti-inflammatory drug (NSAID). The variations of the poly(anhydride-ester) investigated in this article are linked by adipic acid, suberic acid, or sebacic acid. To elucidate the erosion mechanism of these polymers, water uptake, mass loss, contact angle, and changes in device thickness were monitored as a function of in vitro degradation time. The polymers examined here appeared to primarily undergo surface erosion. The adipate homopolymer absorbed the most water and therefore swelled more than the other versions of the poly(anhydride-ester). Additionally, the adipate homopolymer eroded most quickly. Increasing the length of the linker moiety decreased the driving force for hydrolysis, which prolonged the lifetime of the polymer sample.

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Optimized Synthesis of Salicylate-based Poly( anhydride-esters)

Cited by 66 publications

References 16 publications

Synthesis of Poly(ester‐anhydrides) Based on Different Polyester Precursors

Synthesis of Poly(ester‐anhydrides) Based on Different Polyester Precursors

Salicylic Acid-Based Polymers for Guided Bone Regeneration Using Bone Morphogenetic Protein-2

Investigation into the erosion mechanism of salicylate‐based poly(anhydride‐esters)

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