The ethanol extracts were analyzed using Agilent 1100 Series LC/MSD Trap with an electrospray ion source (ESI). All data were acquired employing Agilent Quantitative Analysis data processing software. Chromatographic separation was achieved by gradient elution using Polaris C18‐A column (250 × 4.6 mm) (Varian). The mobile phase consisted of solvent A (0.1% formic acid in water) and solvent B (0.1% formic acid in methanol). The gradient program was as follows: 0–20 min, 50% B; 20–35 min, 50%–80% B; and 35–45 min, 80% B. The flow rate was 1.0 ml/min. The UV detector was set at 280 nm. The LC elute was introduced directly into the ESI interface without flow splitting. The scan range of ESI‐MS was m/z 120–1,200. The ESI voltage was 4.5 kV in positive ion mode. The velocity of 9 L/min and temperature of 325°C of drying gas were applied for ionization using nitrogen. The nebulizer pressure was 40 psi. Relative percentage amount of major components was calculated according to individual peak area and total peak area of LC chromatogram as mean values of three injections from each sample.
Agilent 1100 series lc msd trap
Manufactured by Agilent Technologies
Sourced in United States
The Agilent 1100 Series LC/MSD Trap is a liquid chromatography-mass spectrometry (LC/MS) system. It is designed to provide high-performance liquid chromatography (HPLC) separation and mass spectrometric detection of analytes. The system combines an HPLC with a mass spectrometer equipped with an ion trap mass analyzer.
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Lab products found in correlation
Av 400, by Bruker (2 mentions)
Polaris c18 a column, by Agilent Technologies (1 mentions)
1100 series hplc system, by Agilent Technologies (1 mentions)
Poroshell 120 ec c18 column, by Agilent Technologies (1 mentions)
Nmr spectrophotometer, by Bruker (1 mentions)
Accela uplc system, by Thermo Fisher Scientific (1 mentions)
Avance 3 500 mhz, by Bruker (1 mentions)
Sil g uv254 0.20 mm, by Macherey-Nagel (1 mentions)
Thermo exactive mass spectrometer, by Thermo Fisher Scientific (1 mentions)
Cryoplatform, by Bruker (1 mentions)
P 1020 polarimeter, by Jasco (1 mentions)
Avance 3 600 mhz, by Bruker (1 mentions)
Uv 1800 spectrophotometer, by Shimadzu (1 mentions)
Ft ir 4100 spectrometer, by Jasco (1 mentions)
7 protocols using agilent 1100 series lc msd trap
1
LC-MS Analysis of Ethanol Extracts
2
HPLC-MS Analysis of LRAE Antioxidants
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This assay was performed using the same two preparative Agela P 2010 system with two binary gradient pumps, a diode array detector (DAD) and a visual web detector (VWD), a sample collector and three triple valves, and Agela HPLC software (Agela; Figure 1 ). The C18 column of Megres (250 × 4.6 mm, 5 μm i.d., Hanbon) was carried out for the separation and analysis of LRAE. The reaction coils were assembled by polyetheretherketone (PEEK) tubing (15.0 m × 0.25 mm i.d.). The antioxidant compounds presented in the LRAE were comprehensively analyzed and identified by a HPLC‐MS (Agilent 1100 Series LC/MSD Trap, Agilent Technologies) fitted with an electrospray ionization (ESI) source.
3
Cysteine Labeling with Compounds 5a and 7a
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To a solution of 100 µM cysteine in phosphate-buffered saline (1×, pH 7.5), compound 5a or 7a (100 μM, 5% DMSO) was added and incubated for 10 min at room temperature. The negative labeling control was performed by mock treatment with DMSO. Samples were analyzed by LC/MS using an Agilent 1100 series HPLC system with an Agilent Poroshell 120 EC-C18 column (150 × 2.10 mm 4 μm; mobile phase: ACN/H2O 45:55 + 0.1% formic acid; flow rate: 0.4 ml/min) and electron spray ionization with the Agilent 1100 series LC/MSD Trap in positive ionization mode.
4
Ester Synthesis of trans-2-Butene-1,4-Dicarboxylic Acid
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PTX (0.85 g, 1 mmol), trans-2-butene-1,4-dicarboxylic acid (0.22 g, 1 mmol) and DMAP (0.06 g, 0.2 mmol) were dissolved in 30 mL anhydrous dichloromethane and stirred for 40 min at 0 °C; then, EDCI (0.38 g, 2 mmol) was added, and the mixture was continuously stirred for 1 h. Next, the reaction mixture was returned to room temperature for 2 h under nitrogen atmosphere, and the progress of the reaction was monitored by thin-layer chromatography (TLC). After the reaction, the solution was handled with the same operations described previously to obtain a crude product. Then, the crude product was purified by column chromatography to obtain a white solid (74% yield). The target product was confirmed by mass spectrometry (Agilent 1100 Series LC/MSD Trap) and nuclear magnetic resonance spectroscopy (400 MHz 1H NMR, Bruker AV-400). The assignment of the NMR peaks and MS was analyzed as follows:
5
Detailed Characterization of Synthetic Compounds
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All reagents were obtained from commercial suppliers and used without further purification. The progress of the reactions was monitored by thin-layer chromatography (TLC) on silica gel plates and the spots visualized under ultraviolet (UV) light (254 nm). The column chromatography was performed using 200–300 mesh silica gel (Qingdao Haiyang, Qingdao, China). Mass spectra were measured with an electrospray (ESI-MS) on an Agilent 1100 Series LC/MSD Trap (Agilent Corporation, Santa Clara, CA, USA). 1H-NMR and 13C-NMR spectra were recorded on Bruker NMR spectrophotometers (Karlsruhe, Germany) using DMSO-d6 as the solvent. The IR spectra were measured using a Bruker Fourier number infrared spectrometer (Agilent Corporation, Santa Clara, CA, USA). 1H-NMR, 13C-NMR, ESI-MS and HRMS spectra of the target compounds are available in the Supplementary Material (Figures S1–S80) .
6
Synthesis of DTX Homodimeric Prodrugs
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Three DTX homodimeric prodrugs were synthesized as previously reported with few modifications [20] . Briefly, DTX (646.32 mg, 0.8 mmol) and diacid linker (2, 2′-diselenobisdiglycolic acid, 3, 3′-diselenobisdipropionic acid or 4, 4′-diselenobisdibutyric acid, 0.4 mmol) was added in anhydrous dichloromethane. Then DMAP (9.78 mg, 0.08 mmol) and EDCI (306.72 mg, 1.6 mmol) were added dropwise in above system with stirring for 2 h under nitrogen atmosphere at 25 °C. Then another DMAP (9.78 mg, 0.08 mmol) and EDCI (153.36 mg, 0.8 mmol) were added dropwise for 24 h reaction at 25 °C. Preparative liquid chromatography was utilized to purify the product using acetonitrile/water (70:30) as the mobile phase (yellow solid). Nuclear magnetic resonance spectroscopy (600 MHz 1H NMR, Bruker AV-400) and high-resolution mass spectrometry (Agilent 1100 Series LC/MSD Trap) were applied to confirm the prodrug structure. HPLC was used to identify the purity of the prodrugs.
7
Spectroscopic Characterization of Compounds
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Optical rotation was measured with a JASCO P-1020 polarimeter at 25 °C (JASCO, Gross-Umstadt, Germany). UV spectra were recorded on a Shimadzu UV-1800 spectrophotometer (Shimadzu, Kyoto, Japan) and IR spectra on a JASCO FT-IR (4100) spectrometer. 1 H and 13 C NMR, DEPT and 2D NMR spectra were measured on Bruker Avance III 500 MHz and Bruker Avance III 600 MHz (equipped with a Bruker Cryo Platform) instruments (Bruker, Fällanden, Switzerland). The chemical shift values (δ) are given in ppm and coupling constants in Hz. 1 H and 13 C chemical shifts were referenced to the solvent residual peaks for DMSO-d 6 at δ H 2.49 and δ C 39.5, respectively. HRESIMS experiments were carried out on a Thermo Accela UPLC-system combined with a Thermo Exactive mass spectrometer equipped with an electrospray ion source (Thermo Fisher Scientific, Bremen, Germany). Analytical HPLC was performed on an Agilent 1100 Series LC/MSD trap (Agilent Technologies, Santa Clara, CA, USA). Column chromatography was undertaken using silica gel 60 M (230-400 mesh) or Sephadex LH-20 (Pharmacia Biotech AB, Uppsala, Sweden). TLC analyses were performed on silica gel plates (Sil G/UV254 0.20 mm, Macherey-Nagel, Düren, Germany). All solvents used for chromatography, [α] D , UV and MS were HPLC grade.
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