Transesterification of PHA to Oligomers Covalently Bonded with (Bio)Active Compounds Containing Either Carboxyl or Hydroxyl Functionalities

Kwiecień, Iwona; Kowalczuk, Marek; Adamus, Grażyna

doi:10.1371/journal.pone.0120149

Cited by 19 publications

(38 citation statements)

References 29 publications

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“…Both MALDI and ESI MS, in some cases with the support of MS/MS and/or IM‐MS, have been used in the characterization of polymer conjugates, to confirm the effective functionalization and the success of the synthetic approch . The transesterification reaction of PHAs has been used as a strategic and simple tool for the synthesis of delivery systems for selected bioactive compounds, holding carboxyl or hydroxyl functionalities.…”

Section: Characterization Of Bioresorbable Polymers By Msmentioning

confidence: 99%

“…The transesterification reaction of PHAs has been used as a strategic and simple tool for the synthesis of delivery systems for selected bioactive compounds, holding carboxyl or hydroxyl functionalities. The structures of transesterification products were established at the molecular level by ESI‐MS/MS and 1 H NMR . The transesterification reaction of bacterial biopolymers with tyrosol was applied as a convenient method for obtaining polymer conjugates.…”

Section: Characterization Of Bioresorbable Polymers By Msmentioning

confidence: 99%

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Mass spectrometry in bioresorbable polymer development, degradation and drug‐release tracking

Rizzarelli

Rapisarda

Valenti

2020

Rapid Comm Mass Spectrometry

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A detailed characterization of polymeric matrices and appropriate degradation monitoring techniques are required to sustain the development of new materials as well as to enlarge the applications of the old ones. In fact, polymer analysis is essential for the clarification of the intrinsic relationship between structure and properties that ascertains the industrial applications in diverse fields. In bioresorbable and biodegradable polymers, the role of analytical methods is dual since it is pointed both at the polymeric matrices and at degradation tracking. The structural architectures, the mechanical and morphological properties, and the degradation rate, are of outstanding importance for a specific application. In some cases, the complexity of the polymer structure, the processes of decomposition or the low concentration of the degradation products need the concurrent use of different complementary analytical techniques to give detailed information of the reactions taking place. Several analytical methods are used in bioresorbable polymer development and degradation tracking. Among them, mass spectrometry (MS) plays an essential role and it is used to refine polymer syntheses, for its high sensitivity, to highlight degradation mechanism by detecting compounds present in trace amounts, or to track the degradation product profile and to study drug release. In fact, elucidation of reaction mechanisms and polymer structure, attesting to the purity and detecting defects as well as residual catalysts, in biodegradable and bioresorbable polymers, requires sensitive analytical characterization methods that are essential in providing an assurance of safety, efficacy and quality. This review aims to provide an overview of the MS strategies used to support research and development of resorbable polymers as well as to investigate their degradation mechanisms. It is focused on the most significant studies concerning synthetic bioresorbable matrices (polylactide, polyglycolide and their copolymers, polyhydroxybutyrate, etc.), published in the last ten years.

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Section: Characterization Of Bioresorbable Polymers By Msmentioning

confidence: 99%

Section: Characterization Of Bioresorbable Polymers By Msmentioning

confidence: 99%

Mass spectrometry in bioresorbable polymer development, degradation and drug‐release tracking

Rizzarelli

Rapisarda

Valenti

2020

Rapid Comm Mass Spectrometry

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“…The transesterification of PHA has been used as a tool for the preparation of delivery systems for selected bioac-tive compounds containing either carboxyl or hydroxyl functionalities [15]. The first synthetic strategy was designed for bioactive compounds within the carboxyl group, and these conjugates were obtained through the transesterification of natural PHA.…”

Section: Pha Bioactive Oligomersmentioning

confidence: 99%

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

2017

Self Cite

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Contemporary reports on the bioactive oligomers derived from natural aliphatic co-polyesters (PHA) and their synthetic analogues, formed through anionic ring-opening polymerization (ROP) of β-substituted β-lactones are presented. Synthetic routes for such oligomers, developed mostly by Polish authors, are discussed. The described approaches enable design of novel biodegradable and bioactive oligomers for diverse applications in medicine, cosmetic industry and agrochemistry. Otrzymywanie bioaktywnych oligomerów z naturalnych biopoliestrów i ich syntetycznych analogówStreszczenie: Przedstawiono przegląd aktualnych wyników badań dotyczących bioaktywnych oligomerów otrzymywanych z naturalnych alifatycznych ko-poliestrów (PHA) oraz ich syntetycznych analogów, uzyskanych na drodze anionowej polimeryzacji z otwarciem pierścienia (ROP) β-podstawionych β-laktonów. Omówiono ścieżki syntezy tych oligomerów opracowane głównie przez polskich badaczy. Zaprezentowane metody umożliwiają projektowanie nowych biodegradowalnych, a zarazem bioaktywnych oligomerów mogących znaleźć różnorodne zastosowania w medycynie, przemyśle kosmetycznym i agrochemii.Słowa kluczowe: poliester alifatyczny, anionowa polimeryzacja, oligomer bioaktywny, β-podstawiony β-lakton.

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“…Through a transesterification reaction in the presence of 4-toluenesulfonic acid monohydrate, oligo(3HB-co-4HB) conjugate with (4-chloro-2-methylphenoxy)acetic acid was synthesized in one pot under an argon atmosphere. This conjugate could be used as biodegradable controlled-release systems of pesticides with potentially higher resistance to weather conditions in comparison to conventional forms of pesticides [124]. If a nucleophile (monomethoxy PEG, mPEG) empolyed in the trans- [134,135] esterification under bis(2-ethylhexanoate) tin (catalyst), a PHB-b-mPEG copolymer was formed (Figure 7).…”

Section: Direct Route To Synthesizing Phas Derivativesmentioning

confidence: 99%

Synthetic routes to degradable copolymers deriving from the biosynthesized polyhydroxyalkanoates: A mini review

Ke¹,

Zhang²,

Ramakrishna³

et al. 2016

Express Polym. Lett.

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Abstract.Polyhydroxyalkanoates are a family of natural polyesters being produced as intracellular carbon and energy reserves by a wide variety of microorganisms. They have developed rapidly in both research and development efforts globally in the last 15 years. Till now, over 100 different types of PHAs have been successfully biosynthesized using both genetic engineering and fermentation techniques. Their unique biodegradable, biocompatible and thermoplastic characteristics make PHAs promising candidates for the commodity and biomedical applications. This review focused on the chemical synthesis of the derivatives of the biosynthesized PHAs.

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Transesterification of PHA to Oligomers Covalently Bonded with (Bio)Active Compounds Containing Either Carboxyl or Hydroxyl Functionalities

Cited by 19 publications

References 29 publications

Mass spectrometry in bioresorbable polymer development, degradation and drug‐release tracking

Mass spectrometry in bioresorbable polymer development, degradation and drug‐release tracking

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

Synthetic routes to degradable copolymers deriving from the biosynthesized polyhydroxyalkanoates: A mini review

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