Synthesis, structural characterization, and antiproliferative/cytotoxic effects of a novel modified poly(maleic anhydride-co-vinyl acetate)/doxorubicin conjugate

Karakuş, Gülderen; Ece, Abdulilah; Yağlıoğlu, Ayşe Şahin; Zengin, Hacı Bayram; Karahan, Mesut

doi:10.1007/s00289-016-1821-1

Cited by 10 publications

(15 citation statements)

References 67 publications

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“…[17] It was expressed that CÀ H and C=C vibrations of benzene ring, on DOX, correspond to 793 cm À 1 and a = CÀ H out of plane bending was also observed at 758 and 700 cm À 1 . [18] These peaks mentioned were also obtained in this study as 795, 763 and 707 cm À 1 , respectively. These peaks were also found in the FT-IR spectrum of DOX-PMs.…”

Section: Ft-ir Analysis Of Dox Pcec Pm and Dox-pmssupporting

confidence: 76%

“…stated that the FT‐IR spectrum of DOX showed multiple peaks at 1730 (C−O) and 1577 cm −1 (N−H) [17] . It was expressed that C−H and C=C vibrations of benzene ring, on DOX, correspond to 793 cm −1 and a=C−H out of plane bending was also observed at 758 and 700 cm −1 [18] . These peaks mentioned were also obtained in this study as 795, 763 and 707 cm −1 , respectively.…”

Section: Resultsmentioning

confidence: 99%

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Design and Fabrication of Anticancer Drug‐Loaded Poly(ϵ‐caprolactone)‐Poly(ethylene glycol)‐Poly(ϵ‐caprolactone) Micelles as Controlled Release System

Kocabay¹,

İsmail

2023

ChemistrySelect

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In this study, doxorubicin (DOX) loaded polymeric micelles (PMs) were synthesized based on biodegradable poly(εcaprolactone)-poly(ethylene glycol)-poly(ε-caprolactone) (PCEC) triblock copolymers. So four parameters (shaking speed (rpm) X 1 , time of contact (hour) X 2 , amount of triethylamine (TEA) (μL) X 3 , DOX% X 4 ) were optimized. Then by adding valspodar (PSC 833) or D-α-Tocopherol polyethylene glycol 1000 succinate (TPGS 1000) to the formulations DOX/PSC 833-PMs or DOX/ TPGS 1000-PMs were prepared by a nanoprecipitation method. The synthesized micelles exhibited high drug-loading encapsu-lation efficiency (> 78.98 %), high stability, and pH-dependent drug release. The results showed that the encapsulation efficiencies were not compromised by co-encapsulation of two agents. Finally, it was observed that the association of both DOX and PSC 833 or both DOX and TPGS 1000 within a single micelle formulation elicited the most soluble DOX as compared to DOX loaded formulations (DOX-PMs) while using a lower amount of polymer compared to separated micelle formulations.

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Section: Ft-ir Analysis Of Dox Pcec Pm and Dox-pmssupporting

confidence: 76%

Section: Resultsmentioning

confidence: 99%

Design and Fabrication of Anticancer Drug‐Loaded Poly(ϵ‐caprolactone)‐Poly(ethylene glycol)‐Poly(ϵ‐caprolactone) Micelles as Controlled Release System

Kocabay¹,

İsmail

2023

ChemistrySelect

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“…Poly(maleic anhydride)-based polymers, often used as block copolymers, have provided chemists with a great platform for introducing a variety of lateral functionalities along a polymer backbone, yielding multifunctional materials that have found use in a wide range of applications. − This is facilitated by the effectiveness of reacting anhydride rings with nucleophilic molecules (e.g., H 2 N–R), via the reagent-free nucleophilic attack. As such, the transformation of various poly(maleic anhydride)-based compounds with an array of amine-terminated groups has allowed the preparation of multifunctional polymers that have found use in the surface coating and functionalization of colloidal nanomaterials, ,,− the design of drug delivery vehicles, , and the preparation of antibacterial agents . For instance, the groups of Parak and co-workers and Colvin and co-workers have exploited this reaction route to transform poly(maleic anhydride- alt -1-octadecene), PMAO, into amphiphilic polymers suited for encapsulating colloidal semiconductor nanocrystals (quantum dots, QDs) and iron oxide nanoparticles (IONPs). , Starting with poly(isobutylene- alt -maleic anhydride), PIMA, we have used the nucleophilic addition reaction to prepare a set of hydrophilic multicoordinating ligands and applied them to coat various colloidal nanocrystals (e.g., Au nanostructures, luminescent QDs, and IONPs). ,, Conversely, Haldar and co-workers exploited this transformation reaction, applied to PIMA, to prepare a set of cationic polymers as mimics of antimicrobial peptides and tested their effectiveness against pathogenic bacteria …”

Section: Introductionmentioning

confidence: 99%

“…1−6 This is facilitated by the effectiveness of reacting anhydride rings with nucleophilic molecules (e.g., H 2 N−R), via the reagent-free nucleophilic attack. As such, the transformation of various poly(maleic anhydride)-based compounds with an array of amineterminated groups has allowed the preparation of multifunctional polymers that have found use in the surface coating and functionalization of colloidal nanomaterials, 1,4,6−10 the design of drug delivery vehicles, 2,11 and the preparation of antibacterial agents. 3 For instance, the groups of Parak and co-workers and Colvin and co-workers have exploited this reaction route to transform poly(maleic anhydride-alt-1octadecene), PMAO, into amphiphilic polymers suited for encapsulating colloidal semiconductor nanocrystals (quantum dots, QDs) and iron oxide nanoparticles (IONPs).…”

Section: ■ Introductionmentioning

confidence: 99%

Modification of Poly(maleic anhydride)-Based Polymers with H₂N–R Nucleophiles: Addition or Substitution Reaction?

Jin

Zhang

et al. 2019

Bioconjugate Chem.

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Reacting poly(maleic anhydride)-based polymers with H2N–R nucleophiles is a flexible and highly effective approach for preparing a variety of multifunctional, multicoordinating, and multireactive polymers. The exact transformation of the anhydride ring during this addition reaction is still an open question. In this report, we characterize the transformation of a representative block copolymer, poly(isobutylene-alt-maleic anhydride), with a few H2N–R nucleophiles. In particular, we test the effects of varying a few reaction parameters/conditions (e.g., temperature, solvent, reaction time, and addition of thionyl chloride) on the nature of the anhydride transformation and bond formed between the polymer and the lateral R groups. The resulting polymers are characterized using a combination of analytical techniques including FT-IR, one- and two-dimensional NMR, and gel electrophoresis. We find that the ring opening transformation occurs under mild conditions. Conversely, cyclic imide transformation can take place for reactions carried out at high temperature (e.g., in DMF under refluxing conditions). We also find that use of a protic solvent, such as methanol, or addition of thionyl chloride (SOCl2) to the reaction mixture under refluxing conditions can promote cyclic imide transformation. The cyclic imide transformation is nonetheless partial, as carboxyl groups could still be accounted for in the resulting compounds. Depending on the type of transformation, the resulting polymer can exhibit a few distinct properties, such as net charge buildup along the chain, or the appearance of weak UV–vis absorption and fluorescence properties. These findings are useful for understanding the properties exhibited by polymer materials prepared via this flexible and highly effective route using anhydride containing polymers and oligomers.

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“…1a). Typically BH4bending modes observed around at 1993 cm -1 and B-H stretching modes detected at 2116 cm -1 and 2329 cm -1 [29,30]. According to the selection rules, for a tetrahedral system (BH4ion) only two different IR active modes exist; one bending and one stretching mode.…”

Section: Ftir Analysismentioning

confidence: 99%

Silver Nanoparticles Capped with Poly[(maleic anhydride)-co-(vinyl acetate)]

AYAS

Karakuş

2023

Cumhuriyet Science Journal

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Anhydride containing functional co-polymer, Poly[(maleic anhydride)-co-(vinyl acetate)] (pMAVAc) was synthesized by free radical polymerization reaction presence of methyl ethyl ketone (MEK) media with benzoyl peroxide radical initiation at 80 ◦C. Surface modification of pMAVAc was carried out with silver to obtain size specific silver nanocomposites by well-known chemical-reduction approach. Structural characterizations of the samples were performed spectroscopic measurement and surface morphology identification using Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) spectroscopy and Scanning Electron Microscopy (SEM), respectively. Results obtained from the ATR-FTIR analysis, detection of the characteristic spectrum data of the co-polymer composition in pMAVAc-AgNPs nanocomposite is proof that the co-polymer structure remains unchanged after treatment. The size and morphological properties of the silver nanoparticles were compatible with the characteristic nanomaterial structure and their average size was found to be 35 nm. In addition, as expected, MAVA-AgNPs nanocomposite, the detection of 79.73% Ag by mass is evidence of the high silver content in the material, and it was concluded that the co-polymer was successfully coated with silver. In recent years, considering the increasing importance of biocompatible nanomaterials in drug delivery systems and in pharmaceutical industry, the synthesized nanocomposites are thought to be a useful drug carrier system with potential antibacterial activity.

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Synthesis, structural characterization, and antiproliferative/cytotoxic effects of a novel modified poly(maleic anhydride-co-vinyl acetate)/doxorubicin conjugate

Cited by 10 publications

References 67 publications

Design and Fabrication of Anticancer Drug‐Loaded Poly(ϵ‐caprolactone)‐Poly(ethylene glycol)‐Poly(ϵ‐caprolactone) Micelles as Controlled Release System

Design and Fabrication of Anticancer Drug‐Loaded Poly(ϵ‐caprolactone)‐Poly(ethylene glycol)‐Poly(ϵ‐caprolactone) Micelles as Controlled Release System

Modification of Poly(maleic anhydride)-Based Polymers with H₂N–R Nucleophiles: Addition or Substitution Reaction?

Silver Nanoparticles Capped with Poly[(maleic anhydride)-co-(vinyl acetate)]

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Synthesis, structural characterization, and antiproliferative/cytotoxic effects of a novel modified poly(maleic anhydride-co-vinyl acetate)/doxorubicin conjugate

Cited by 10 publications

References 67 publications

Design and Fabrication of Anticancer Drug‐Loaded Poly(ϵ‐caprolactone)‐Poly(ethylene glycol)‐Poly(ϵ‐caprolactone) Micelles as Controlled Release System

Design and Fabrication of Anticancer Drug‐Loaded Poly(ϵ‐caprolactone)‐Poly(ethylene glycol)‐Poly(ϵ‐caprolactone) Micelles as Controlled Release System

Modification of Poly(maleic anhydride)-Based Polymers with H2N–R Nucleophiles: Addition or Substitution Reaction?

Silver Nanoparticles Capped with Poly[(maleic anhydride)-co-(vinyl acetate)]

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Product

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Modification of Poly(maleic anhydride)-Based Polymers with H₂N–R Nucleophiles: Addition or Substitution Reaction?