Dataset Information

Antiviral drug Triazavirin, selectively labeled with ²H, ¹³C, and ¹⁵N stable isotopes. Synthesis and properties.

ABSTRACT: Isotope-labeled antiviral drug Triazavirin containing ²H, ¹³C, and ¹⁵N atoms in its structure has been synthesized. ¹³C²H₃I and KS¹³CN served as donors of ¹³C isotopes. The use of ¹³С-MeI containing ²H atoms made it possible to additionally incorporate deuterium labels into the structure of the compound. The ¹⁵N atoms were incorporated using ¹⁵N-enriched sodium nitrite, aminoguanidine carbonate, and ethyl nitroacetate. The resulting ²H₃,¹³C₂,¹⁵N₃-Triazavirin was characterized by NMR spectroscopy.

Supplementary information

The online version contains supplementary material available at 10.1007/s10593-021-02927-1.

SUBMITTER: Shestakova TS

PROVIDER: S-EPMC8113018 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Antiviral drug Triazavirin, selectively labeled with 2H, 13C, and 15N stable isotopes. Synthesis and properties.

Shestakova Tatyana S TS Deev Sergey L SL Khalymbadzha Igor А IА Rusinov Vladimir L VL Paramonov Alexander S AS Arseniev Alexander S AS Shenkarev Zakhar O ZO Charushin Valery N VN Chupakhin Oleg N ON

Chemistry of heterocyclic compounds 20210512 4

Isotope-labeled antiviral drug Triazavirin containing 2H, 13C, and 15N atoms in its structure has been synthesized. 13C2H3I and KS13CN served as donors of 13C isotopes. The use of 13С-MeI containing 2H atoms made it possible to additionally incorporate deuterium labels into the structure of the compound. The 15N atoms were incorporated using 15N-enriched sodium nitr ...[more]

PMID: 33994553

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Project description:Synthetic Cry1Ab/Ac proteins expressed by genetically modified (GM) crops have a high potential to control insect pests without utilizing large amounts of chemical insecticides. Before these crops are used in agriculture, the environmental fate and interactions in the soil must be understood. Stable isotope-labeled Cry1Ab/Ac protein is a highly useful tool for collecting such data. We developed a protocol to produce 13 C/15 N single-labeled Cry proteins. The artificially synthesized gene Cry1Ab/Ac of Bt rice Huahui No. 1, which has been certified by the Chinese government to be safe for human consumption, was subcloned into pUC57, and the expression vector pET-28a-CryAb/Ac was constructed and transformed into Escherichia coli BL21 (DE3) competent cells. Next, 0.2 mM isopropyl thiogalactoside (IPTG) was added to these cells and cultured at 37°C for 4 h to induce the synthesis and formation of inclusion bodies in M9 growth media containing either [U-13 C] glucose (5% 13 C-enriched) or [15 N] ammonium chloride (5% 15 N-enriched). Then, Cry inclusion bodies were dissolved in urea and purified by affinity chromatography under denaturing conditions, renatured by dialysis, and further detected by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) and Western blotting. The purities of 13 C/15 N-labeled Cry proteins reached 99% with amounts of 12.6 mg/L and 8.8 mg/L, respectively. The δ 13 C and ä 15 N values of 13 C-labeled Cry protein and 15 N-labeled Cry protein were 3,269‰ and 2,854‰, respectively. A bioassay test revealed that the labeled Cry1Ab/Ac proteins had strong insecticidal activity. The stable isotope-labeled insecticidal Cry proteins produced for the first time in this study will provide an experimental basis for future metabolic studies on Cry proteins in soil and the characteristics of nitrogen (N) and carbon (C) transformations. Our findings may also be employed as a reference for elucidating the environmental behavior and ecological effects of BT plants and expressed products.

Dataset Information

Antiviral drug Triazavirin, selectively labeled with ²H, ¹³C, and ¹⁵N stable isotopes. Synthesis and properties.

Supplementary information

Publications

Antiviral drug Triazavirin, selectively labeled with <sup>2</sup>H, <sup>13</sup>C, and <sup>15</sup>N stable isotopes. Synthesis and properties.

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