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An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine.

ABSTRACT: An improved five-step synthesis of triethylene glycol-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine (6) is described. Using cost-effective starting materials, the developed synthesis route was synthetic, efficient, and chromatographic purification-free. The key point of the work is the one-pot synthesis of tert-butyl methyl(4-vinylphenyl)carbamate through methylation and elimination in the NaH/THF system. The new synthesis route shows the potential to achieve scaled-up preparation of 6 in the future.

SUBMITTER: Jia J

PROVIDER: S-EPMC7424578 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine.

Jia Jianhua J Wei Huiqiang H Duan Yuqing Y Ning Hongxin H Yu Jiang J Zhu Yuan Y Hou Wenbin W Li Yiliang Y

ACS omega 20200730 31

An improved five-step synthesis of triethylene glycol-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine (6) is described. Using cost-effective starting materials, the developed synthesis route was synthetic, efficient, and chromatographic purification-free. The key point of the work is the one-pot synthesis of tert-butyl methyl(4-vinylphenyl)carbamate through methylation and elimination in the NaH/THF system. The new synthesis route shows the potential to achieve sca ...[more]

PMID: 32803038

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Project description:This paper introduces a new class of amphiphilic block copolymers created by combining two polymers: polylactic acid (PLA), a biocompatible and biodegradable hydrophobic polyester used for cargo encapsulation, and a hydrophilic polymer composed of oligo ethylene glycol chains (triethylene glycol methyl ether methacrylate, TEGMA), which provides stability and repellent properties with added thermo-responsiveness. The PLA-b-PTEGMA block copolymers were synthesized using ring-opening polymerization (ROP) and reversible addition-fragmentation chain transfer (RAFT) polymerization (ROP-RAFT), resulting in varying ratios between the hydrophobic and hydrophilic blocks. Standard techniques, such as size exclusion chromatography (SEC) and 1H NMR spectroscopy, were used to characterize the block copolymers, while 1H NMR spectroscopy, 2D nuclear Overhauser effect spectroscopy (NOESY), and dynamic light scattering (DLS) were used to analyze the effect of the hydrophobic PLA block on the LCST of the PTEGMA block in aqueous solutions. The results show that the LCST values for the block copolymers decreased with increasing PLA content in the copolymer. The selected block copolymer presented LCST transitions at physiologically relevant temperatures, making it suitable for manufacturing nanoparticles (NPs) and drug encapsulation-release of the chemotherapeutic paclitaxel (PTX) via temperature-triggered drug release mechanism. The drug release profile was found to be temperature-dependent, with PTX release being sustained at all tested conditions, but substantially accelerated at 37 and 40 °C compared to 25 °C. The NPs were stable under simulated physiological conditions. These findings demonstrate that the addition of hydrophobic monomers, such as PLA, can tune the LCST temperatures of thermo-responsive polymers, and that PLA-b-PTEGMA copolymers have great potential for use in drug and gene delivery systems via temperature-triggered drug release mechanisms in biomedicine applications.

Project description:Triethylene glycol dimethacrylate (TEGDMA) is a diluent monomer used pervasively in dental composite resins. Through hydrolytic degradation of the composites in the oral cavity it yields a hydrophilic biodegradation product, triethylene glycol (TEG), which has been shown to promote the growth of Streptococcus mutans, a dominant cariogenic bacterium. Previously it was shown that TEG up-regulated gtfB, an important gene contributing to polysaccharide synthesis function in biofilms. However, molecular mechanisms related to TEG's effect on bacterial function remained poorly understood. In the present study, S. mutans UA159 was incubated with clinically relevant concentrations of TEG at pH 5.5 and 7.0. Quantitative real-time PCR, proteomics analysis, and glucosyltransferase enzyme (GTF) activity measurements were employed to identify the bacterial phenotypic response to TEG. A S. mutans vicK isogenic mutant (SM?vicK1) and its associated complemented strain (SM?vicK1C), an important regulatory gene for biofilm-associated genes, were used to determine if this signaling pathway was involved in modulation of the S. mutans virulence-associated genes. Extracted proteins from S. mutans biofilms grown in the presence and absence of TEG were subjected to mass spectrometry for protein identification, characterization and quantification. TEG up-regulated gtfB/C, gbpB, comC, comD and comE more significantly in biofilms at cariogenic pH (5.5) and defined concentrations. Differential response of the vicK knock-out (SM?vicK1) and complemented strains (SM?vicK1C) implicated this signalling pathway in TEG-modulated cellular responses. TEG resulted in increased GTF enzyme activity, responsible for synthesizing insoluble glucans involved in the formation of cariogenic biofilms. As well, TEG increased protein abundance related to biofilm formation, carbohydrate transport, acid tolerance, and stress-response. Proteomics data was consistent with gene expression findings for the selected genes. These findings demonstrate a mechanistic pathway by which TEG derived from commercial resin materials in the oral cavity promote S. mutans pathogenicity, which is typically associated with secondary caries.

Dataset Information

An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine.

Publications

An Improved Synthesis of the Triethylene Glycol-Substituted 4-(<i>N</i>-Methyl-<i>N</i>-Boc-Amino)Styrylpyridine.

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