Molecular architecture of novel potentially bioactive (co)oligoesters containing pesticide moieties established by electrospray ionization multistage mass spectrometry

Kwiecień, Iwona; Bałakier, Tomasz; Jurczak, Janusz; Kowalczuk, Marek; Adamus, Grażyna

doi:10.1002/rcm.7133

Cited by 14 publications

(17 citation statements)

References 31 publications

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“…Recently, ESI-MS has been successfully applied in the structural studies of conjugates of biodegradable oligomers and bioactive substances, such as food preservatives [24], herbicides [25,26], non-steroidal anti-inflammatory drugs [27,28], or antioxidants used in cosmetology [29,30,31]. …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System

Kwiecień

Adamus

2016

Materials

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The (trans)esterification reaction of bacterial biopolymers with a selected bioactive compound with a hydroxyl group was applied as a convenient method for obtaining conjugates of such compound. Tyrosol, a naturally occurring phenolic compound, was selected as a model of a bioactive compound with a hydroxyl group. Selected biodegradable polyester and polyamide, poly(3-hydroxybutyrate-co-4-hydroxybutyrate) (P(3HB-co-4HB)) and poly-γ-glutamic acid (γ-PGA), respectively, were used. The (trans)esterification reactions were carried out in melt mediated by 4-toluenesulfonic acid monohydrate. The structures of (trans)esterification products were established at the molecular level with the aid of ESI-MS2 (electrospray ionization tandem mass spectrometry) and/or 1H NMR (nuclear magnetic resonance) techniques. Performed analyses confirmed that the developed method leads to the formation of conjugates in which bioactive compounds are covalently bonded to biopolymer chains. The amount of covalently bonded bioactive compounds in the resulting conjugates depends on the type of biopolymers applied in synthesis.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System

Kwiecień

Adamus

2016

Materials

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“…11 Furthermore, the synthetic approach for the biodegradable release systems based on anionic homo-and copolymerization of respective β-substituted β-lactones containing MCPA moieties was reported. 12 However, the alternative approach of producing PHA-MCPA conjugates via the transesterification of natural PHA, would seem to be more pragmatic, from both a technological and economic point of view.…”

Section: Introductionmentioning

confidence: 99%

Biodegradable PBAT/PLA Blend with Bioactive MCPA-PHBV Conjugate Suppresses Weed Growth

et al. 2018

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The herbicide 2-methyl-4-chlorophenoxyacetic acid (MCPA) conjugated with poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) was prepared via a melt transesterification route. The resultant bioactive oligomer was then mixed with a blend of polylactide (PLA) and poly(butylene adipate-co-terephthalate) (PBAT) with different loadings to manufacture films to be used as a bioactive, biodegradable mulch to deliver the herbicide to target broadleaf weed species. The biological targeting of the MCPA-PHBV conjugate in the mulch film was investigated under glasshouse conditions using faba bean (Vicia faba) as a selective (nontarget) model crop species having broadleaf morphology. The presence of the MCPA-PHBV conjugate in the biodegradable PBTA/PLA blend was shown to completely suppress the growth of broadleaf weed species while displaying only a mild effect on the growth of the model crop. The degradation of the mulch film under glasshouse conditions was quite slow. The release of the MCPA-PHBV during this process was detected using NMR, GPC, EDS, and DSC analyses, indicating that the majority of the MCPA diffused out after MCPA-PHBV conjugate bond scission. These data provide a strong "proof of concept" and show that this biodegradable, bioactive film is a good candidate for future field applications and may be of wide agricultural applicability.

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“…Incorporation of bioactive compounds into the β-lactones structure may lead to homo-and co-oligoesters with a bioactive moiety covalently linked as pendent groups along an oligomer backbone. This synthetic strategy was applied by us for preparation of the PHA synthetic analogues with ibuprofen pendant groups [44], pesticide moieties [45] and recently antioxidants used in cosme tics [46]. The respective synthetic pathway, presented on Scheme I shows synthesis of bioactive co-oligoesters via copolymerization of BL with β-substituted β-lactones containing covalently bonded selected bioactive moieties [e.g., ibuprofen, (4-chloro-2-methylphenoxy)acetic acid, and anisic acid].…”

Section: Bioactive Oligomers Of Pha Analoguesmentioning

confidence: 99%

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

2017

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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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Molecular architecture of novel potentially bioactive (co)oligoesters containing pesticide moieties established by electrospray ionization multistage mass spectrometry

Cited by 14 publications

References 31 publications

Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System

Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System

Biodegradable PBAT/PLA Blend with Bioactive MCPA-PHBV Conjugate Suppresses Weed Growth

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

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