Dataset Information

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: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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