Formation of epoxide-amine oligo-adducts as OH-functionalized initiators for the ring-opening polymerization of <i>ε</i>-caprolactone

Theis, Julia; Ritter, Helmut

doi:10.3762/bjoc.6.105

Cited by 6 publications

(3 citation statements)

References 22 publications

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“…We have employed ring-opening polymerization between diglycidyl ethers (diepoxides) and polyamines 31-34 for the formation of combinatorial polymer libraries for transgene delivery35,36. Recently, it was found that a polymer 1,4 C-1,4 Bis, generated in our laboratory from 1,4-cyclohexanedimethanol diglycidyl ether (1,4C) and 1,4-bis(3-aminopropyl) piperazine) (1,4Bis) monomers demonstrated higher transgene expression than 25 kDa PEI at certain polymer:DNA weight ratios 36,37.…”

Section: Introductionmentioning

confidence: 99%

Generation of a Focused Poly(amino ether) Library: Polymer-mediated Transgene Delivery and Gold-Nanorod based Theranostic Systems

Vu¹,

Ramos²,

Potta³

et al. 2012

Theranostics

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A focused library of twenty-one cationic poly(amino ethers) was synthesized following ring-opening polymerization of two diglycidyl ethers by different oligoamines. The polymers were screened in parallel for plasmid DNA (pDNA) delivery, and transgene expression efficacies of individual polymers were compared to those of 25 kDa polyethylenimine (PEI), a current standard for polymer-mediated transgene delivery. Seven lead polymers that demonstrated higher transgene expression than PEI in pancreatic and prostate cancer cells lines were identified from the screen. All seven lead polymers showed highest transgene expression at a polymer:pDNA weight ratio of 5:1 in the MIA PaCa-2 pancreatic cancer cell line. Among the conditions studied, transgene expression efficacy correlated with minimal polymer cytotoxicity but not polyplex sizes. In addition, this study indicated that methylene spacing between amine centers in the monomers, amine content, and molecular weight of the polymers are all significant factors and should be considered when designing polymers for transgene delivery. A lead effective polymer was employed for coating gold nanorods, leading to theranostic nanoassemblies that possess combined transgene delivery and optical imaging capabilities, leading to potential theranostic systems.

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Section: Introductionmentioning

confidence: 99%

Generation of a Focused Poly(amino ether) Library: Polymer-mediated Transgene Delivery and Gold-Nanorod based Theranostic Systems

Vu¹,

Ramos²,

Potta³

et al. 2012

Theranostics

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“…Moreover, 1-methyl-1-cyclohexene has been used as a source of hydrogen with the obvious advantage of producing the safer toluene as the oxidized product. MW-assisted Pd/C-catalyzed reduction of aromatic nitro groups [84] and nitrile in 4-(2,3-epoxypropyl-1-oxy)benzonitrile, 108, took place in good yields using 1-methyl-1-cyclohexene as a H2 donor (Scheme 31) [85]. Cyclohexene has also been used as hydrogen donor in the reduction of the nitro derivative 110, a key intermediate in the synthesis of the powerful canonical transient receptor potential channel (TRPC) inhibitor Pyr3, 112 (Scheme 32) [86].…”

Section: Other Hydrogen Sourcesmentioning

confidence: 99%

Pd/C Catalysis under Microwave Dielectric Heating

2017

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Microwave-assisted organic synthesis (MAOS) provides a novel and efficient means of achieving heat organic reactions. Nevertheless, the potential arcing phenomena via microwave (MW) interaction with solid metal catalysts has limited its use by organic chemists. As arcing phenomena are now better understood, new applications of Pd/C-catalyzed reactions under MW dielectric heating are now possible. In this review, the state of the art, benefits, and challenges of coupling MW heating with heterogeneous Pd/C catalysis are discussed to inform organic chemists about their use with one of the most popular heterogeneous catalysts.

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“…Diglycidyl ether can be differentiated from other organic compounds by the presence of two terminal oxirane groups, which are able to react with compounds possessing active hydrogen atoms, including amines [ 1 ], amides or mercaptans [ 2 ] and alcohols [ 3 , 4 ]. Glycidyl ethers have been widely used since the late 1940s as basic components of epoxy resins [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Liquid Crystalline Diglycidyl Ethers

Mohammed

Hamidi

2012

Molecules

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The phenolic Schiff bases I–VI were synthesized by condensation reactions between various diamines, namely o-dianisidine, o-tolidine and ethylenediamine with vanillin or p-hydroxybenzaldehyde and subsequent reactions between these phenolic Schiff bases and epichlorohydrin to produce new diglycidyl ethers Ia–VIa. The structures of these compounds were confirmed by CHN, FT-IR, 1H-NMR, and 13C-NMR spectroscopy. Their thermotropic liquid crystalline behavior was studied using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). All the diglycidyl ethers prepared exhibit nematic mesophases, except for Va and VIa, which did not show any transition mesophases, but simply flow to liquids.

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Formation of epoxide-amine oligo-adducts as OH-functionalized initiators for the ring-opening polymerization of ε-caprolactone

Cited by 6 publications

References 22 publications

Generation of a Focused Poly(amino ether) Library: Polymer-mediated Transgene Delivery and Gold-Nanorod based Theranostic Systems

Generation of a Focused Poly(amino ether) Library: Polymer-mediated Transgene Delivery and Gold-Nanorod based Theranostic Systems

Pd/C Catalysis under Microwave Dielectric Heating

Synthesis of New Liquid Crystalline Diglycidyl Ethers

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