Facile synthesis of drug-conjugated PHPMA core-crosslinked star polymers

Tucker, Bryan S.; Getchell, Stephen G.; Hill, Megan R.; Sumerlin, Brent S.

doi:10.1039/c5py00497g

Cited by 47 publications

(41 citation statements)

References 59 publications

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“…Development of reusable heterogeneous catalysts is one of the most important subjects in organic synthesis and organometallic catalysis due to the economic and environmental concerns . Different substrates such as porous materials or particles, metal–organic‐frameworks, and crosslinked polymers have been used to carry metal ions or particles as solid catalysts for the mediation of various reactions. However, compared with homogeneous systems, there are still some challenges such as low catalytic efficiency and gradually declined activity after reuse .…”

Section: Introductionmentioning

confidence: 99%

Development of dipyridine‐based coordinative polymers for reusable heterogeneous catalysts

Chang

Lin

et al. 2019

J Chinese Chemical Soc

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Poly(di(pyridin‐2‐yl)methyl acrylate) (PDPyMA), which was obtained by the free radical polymerization of designed coordinative monomer of di(pyridin‐2‐yl)methyl acrylate, is able to coordinate with various metal ions to form heterogeneous catalysts for diverse catalytic reactions. The Pd and Cu complexes supported by PDPyMA were developed for the heterogeneous Suzuki‐Miyaura reaction and Friedel‐Crafts alkylation, respectively. The PDPyMA‐based catalysts showed no significant decline of reactivity after five times recycling. However, the hydrolysis of the PDPyMA backbone under alkaline conditions limited the catalytic efficiency of this heterogeneous catalyst so that the coordinative monomer was redesigned as 1,1‐di(pyridine‐2‐yl)‐2‐(4‐vinylphenyl)ethan‐1‐ol and then 2,2′‐(1‐methoxy‐2‐(4‐vinylphenyl)ethane‐1,1‐diyl)dipyridine (MVPhDPy). With copolymerization of N‐isopropyl acrylamide (NIPAM), the efficiency of polymer‐based heterogeneous catalysts could be further raised, demonstrated by the increased turn over number in the Suzuki‐Miyaura reaction, which approached 5,260 by using the catalyst formed from poly(MVPhDPy‐co‐NIPAM) and Pd(OAc)2. poly(MVPhDPy‐co‐NIPAM) copolymer, therefore, could be a versatile platform to support different metal ions for various heterogeneous catalytic reactions.

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Section: Introductionmentioning

confidence: 99%

Development of dipyridine‐based coordinative polymers for reusable heterogeneous catalysts

Chang

Lin

et al. 2019

J Chinese Chemical Soc

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“…Nanostructured polymers that have branched topologies, large surface area, and empty interior volume are considered unimolecular containers for encapsulation, [1][2][3][4] protection, [ 5 ] and controlled release [ 6,7 ] of active "cargoes" [ 8 ] in applications of pharmaceuticals, [ 9,10 ] personal care [ 11 ] and catalysis. [ 12 ] So far, various types of unimolecular…”

Section: Introductionmentioning

confidence: 99%

Comparison of Loading Efficiency between Hyperbranched Polymers and Cross‐Linked Nanogels at Various Branching Densities

Graff

Shi

Wang

et al. 2015

Macromol. Rapid Commun.

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The effect of branching point structures and densities is studied between azido-containing hyperbranched polymers and cross-linked nanogels on their loading efficiency of alkynyl-containing dendron molecules. Hyperbranched polymers that contained "T"-shaped branching linkage from which three chains radiated out and cross-linked nanogels that contained "X"-shaped branching linkage with four radiating chains are synthesized in microemulsion using either atom transfer radical polymerization (ATRP) or conventional radical polymerization (RP) technique. Both polymers have similar density of azido groups in the structure and exhibit similar hydrodynamic diameter in latexes before purification. Subsequent copper-catalyzed azide-alkyne cycloaddition reactions between these polymers and alkynyl-containing dendrons in various sizes (G1-G3) demonstrate an order of dendron loading efficiencies (i.e., final conversion of alkynyl-containing dendron) as hyperbranched polymers > nanogels synthesized by ATRP > nanogels synthesized by RP. Decreasing the branching density or using smaller dendron molecules increases the click efficiency of both polymers. When G2 dendrons with a molecular weight of 627 Da are used to click with the hyperbranched polymers composed of 100% inimer, a maximum loading efficiency of G2 in the loaded hyperbranched polymer is 58% of G2 by weight. These results represent the first comparison between hyperbranched polymers and cross-linked nanogels to explore the effect of branching structures on their loading efficiencies.

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“…This CTA is known to control the polymerization of methacrylamide monomers and has been widely used to prepare well-defined PHPMA homopolymers and copolymers. 14, 16 A PHPMA homopolymer with a molecular weight of 8.0 kg/mol and a narrow molecular weight distribution ( M w / M n = 1.1) was obtained, as evidenced by gel permeation chromatography (Fig. S1).…”

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confidence: 96%

“…16 Our group previously synthesized core-crosslinked star polymers which conjugated the hydroxyl group of PHPMA to the carboxyl functionality of the anticancer drug methotrexate. 14 Here, we demonstrate that modifying HPMA with valproic acid (VPA) will render the resulting polymer sufficiently hydrophobic to form amphiphilic block copolymers where both blocks are based on PHPMA. In this way, the functionalized block can serve as the micellar core loaded with a covalently bound drug for enhanced stability.…”

mentioning

confidence: 97%

“…14, 15 Hennink and coworkers previously reported block copolymers of HPMA with HPMA-dilactate, where hydrolysis under basic conditions (pH 10) led to hydrolysis and liberation of HPMA units to achieve a completely hydrophilic polymer. 16 Our group previously synthesized core-crosslinked star polymers which conjugated the hydroxyl group of PHPMA to the carboxyl functionality of the anticancer drug methotrexate.…”

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confidence: 99%

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Poly(N-(2-hydroxypropyl)methacrylamide)–valproic acid conjugates as block copolymer nanocarriers

et al. 2017

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Facile synthesis of drug-conjugated PHPMA core-crosslinked star polymers

Abstract: Poly(N-(2-hydroxypropyl)methacrylamide) (PHPMA), a biocompatible and non-immunogenic polymer, was used to form core-crosslinked star polymers for potential drug delivery applications.

Cited by 47 publications

References 59 publications

Development of dipyridine‐based coordinative polymers for reusable heterogeneous catalysts

Development of dipyridine‐based coordinative polymers for reusable heterogeneous catalysts

Comparison of Loading Efficiency between Hyperbranched Polymers and Cross‐Linked Nanogels at Various Branching Densities

Poly(N-(2-hydroxypropyl)methacrylamide)–valproic acid conjugates as block copolymer nanocarriers

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