Optical rotation values were recorded on a polarimeter (Anton-Paar MCP 200; Austria). Infrared (IR) spectra were obtained with a Fourier transform infrared spectrometer (IFS-55; Bruker). A Shimadzu UV-1700 spectrophotometer (Shimadzu, Kyoto, Japan) was used to obtain the ultraviolet (UV) spectra. The NMR spectra were recorded using ARX-400 and AV-600 spectrometers (Bruker) with TMS as an internal standard. HRESIMS data were recorded on an Agilent G6520 Q-TOF spectrometer (Santa Clara, CA, USA). Column chromatography was conducted using silica gel (100–200 mesh and 200–300 mesh, Qingdao, China) and ODS (50 μm, Aichi, Japan) as absorbents, and thin-layer chromatography (TLC) plates (GF254) were purchased from Qingdao Marine Chemical Co. Ltd. (Qingdao, China). High-performance liquid chromatography (HPLC) was performed using a Shimadzu LC-20AR instrument equipped with an SPD-20A UV detector (Shimadzu, Kyoto, Japan) and a YMC Rp-C18 column (5 μm, 10 × 250 mm) (YMC, Kyoto, Japan). Cell apoptosis and intracellular ROS measurements were analyzed using a Becton Dickinson FACS Calibur System. All solvents used for isolation were of analytical grade, and the reagents for HPLC were of chromatographic grade.
Av 600 spectrometer
Manufactured by Bruker
Sourced in Germany, United States, Switzerland
The AV-600 spectrometer is a nuclear magnetic resonance (NMR) instrument manufactured by Bruker. It is designed to perform high-resolution NMR spectroscopy analysis on a variety of samples. The AV-600 operates at a frequency of 600 MHz, providing high-quality data for applications in chemistry, materials science, and other related fields.
Automatically generated - may contain errors
Lab products found in correlation
Av 400, by Bruker (6 mentions)
Av 400 spectrometer, by Bruker (5 mentions)
Silica gel, by Qingdao Marine Chemical (4 mentions)
Sephadex lh 20, by GE Healthcare (4 mentions)
Uv 2550 spectrophotometer, by Shimadzu (3 mentions)
Sephadex lh 20, by Cytiva (3 mentions)
Acarbose, by Merck Group (3 mentions)
Gel ods a, by YMC (3 mentions)
Biotek synergy h1, by Agilent Technologies (3 mentions)
1525 binary hplc pump, by Waters Corporation (3 mentions)
5 mm cptci cryoprobe, by Bruker (3 mentions)
Tensor 27 ftir spectrometer, by Bruker (3 mentions)
Av 300 spectrometer, by Bruker (3 mentions)
Nicolet 6700 ft ir, by Thermo Fisher Scientific (3 mentions)
Topspin 3, by Bruker (3 mentions)
Rp c18 column, by YMC (2 mentions)
Spd 20a uv detector, by Shimadzu (2 mentions)
Uv 2201 spectrophotometer, by Shimadzu (2 mentions)
P 1020 digital polarimeter, by Jasco (2 mentions)
J 715 spectropolarimeter, by Jasco (2 mentions)
118 protocols using av 600 spectrometer
1
Spectroscopic and Chromatographic Analysis
2
Analytical Characterization of Compounds
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The NMR spectra were recorded using Bruker BioSpin AV-300 and AV-600 spectrometers. The ESI-MS spectra were recorded using a Bruker Daltonics micrOTOF Q-III spectrometer (Bruker Daltonics, Billerica, MA, USA). The HPLC and GPC measurements were conducted using a system consisting of a JASCO PU-2089 pump and a JASCO CO-2065 column oven (JASCO Corporation, Tokyo, Japan). A JASCO UV-2075 ultraviolet detector and a JASCO RI-2031 refractive index detector were used for the HPLC and GPC analyses, respectively. A 5C18-MS-II column (ɸ4.6 × 250 mm, Nacalai Tesque, INC.) was used for the HPLC analysis. 5, 4, 3, and 10 % MeCN-containing water were used as the eluents at a flow rate of 1.0 mL/min at 30 °C to analyze the enzymatic reaction with 1a – d , respectively. A Shodex OHpak SB-804 HQ column (ɸ8.0 × 300 mm, Showa Denko K.K., Tokyo, Japan) was used for the GPC analysis of 3a – c using a phosphate buffer (20 mM, pH 7.0) as the eluent at a flow rate of 0.5 mL/min at 30 °C. Pullulan samples were used as standards. A Shodex KD-804 column (ɸ8.0 × 300 mm, Showa Denko K.K.) was used for the GPC analysis of 3d using N , N -dimethylformamide (DMF) containing 10 mM lithium bromide as the eluent at a flow rate of 0.5 mL/min at 50 °C. Poly(methylmethacrylate) samples were used as standards. The fluorescence intensity was recorded using a JASCO FP-6500 fluorometer for the lectin binding tests.
3
Spectroscopic Analysis of Organic Compounds
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Optical rotations were recorded on a Perkin-Elmer 241 polarimeter. UV spectra were measured on a Shimadzu UV 2201 spectrophotometer. IR spectra were recorded on a Bruker IFS 55 spectrometer. Bruker AV-400 and AV-600 spectrometers were used in the NMR experiments. Chemical shift values were expressed in δ (ppm) using the peak signals of the solvent DMSO-d6 (δH 2.50 and δC 39.51) as references, and coupling constants (J in Hz) were given in parentheses. HRESIMS data were acquired on an Agilent 6210 TOF mass spectrometer. Silica gel GF254 prepared for TLC was purchased from Qingdao Marine Chemical Factory (Qingdao, China). Silica gel (200–300 mesh, Qingdao Marine Chemical Factory, Qingdao, China), Sephadex LH-20 (Pharmacia, USA), and octadecyl Silica gel (Merck Chemical Company Ltd., German) were used for column chromatography (CC). RP-HPLC separations were conducted using an LC-6AD liquid chromatograph and a SPD-20A UV detector (Shimadzu, Kyoto, Japan) with a RP-C18 column (250 × 20 mm, 120 Å, 5 μm, YMC Co. Ltd.).
4
Analytical Techniques for Natural Product Characterization
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Nuclear magnetic resonance (NMR) spectra were recorded on Bruker AV-400, and AV-600 spectrometers (Bruker, Billerica, MA, USA). Chemical shifts were expressed in δ (ppm) with tetramethylsilane as an internal standard. HR-ESI-MS spectra were recorded on a Bruker micro-TOF-Q mass spectrometer; IR spectra were obtained using a Bruker IFS-55 Fourier transform infrared spectrometer (Bruker). Preparative RP-HPLC was carried out on an Agela P1050 pump and Agela UV1000D UV spectrophotometric detector at 210 nm using a Round C18 250 × 20 mm (Media: 10 nm, 5 nm. Ser. No: B617111003) eluted with gradient CH3OH–H2O or CH3OH–H2O–CF3COOH solvent systems. Flash chromatography was carried out on an Agela Cheetah Flash System using an ODS Flash Column (spec: C-18, 80 g, 120 g, 20–45 mm; Tianjin Agela Technologies Co., Ltd.). Open-column chromatography was performed using silica gel.
5
Comprehensive Analytical Techniques for Chemical Characterization
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Melting points were measured on a Buchi melting point B-540 visual thermometer or Fisher-Johns melting point apparatus. The UV spectra were recorded with a PerkinElmer or Varian Cary 5000 UV-vis NIR spectrophotometer. IR spectra were recorded on a PerkinElmer FTS FT-IR spectrometer or a Perkin Elmer Frontier Optica FT-IR spectrophotometer. The NMR spectra were recorded on 400 MHz Bruker FT-NMR Ultra Shield and 600 MHz Bruker AV-600 spectrometers with tetramethylsilane as the internal standard. HRESITOFMS spectra were measured on a Bruker-Hewlett-Packard 1100 Esquire-LC system mass spectrometer. Quick column chromatography (QCC) and column chromatography (CC) were performed on silica gel C60 (0-20 µm, SiliCycle® Inc.) and silica gel G60 (60-200 µm, SiliCycle® Inc.), respectively. Sephadex LH-20, when indicated, was also used for CC. Precoated TLC plates of silica gel 60 F254 were used for analytical purposes.
6
Ovarian Cancer Bioluminescence Imaging
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All chemicals were purchased from commercial suppliers and used without further purification. Ultrapure water was purified with a Mill-Q filtration system. UV-visible absorbance spectra were obtained on a PUXI TU-1901 spectrophotometer. Highpressure liquid chromatography (HPLC) spectra and the purity of the compounds were determined by analytical reverse-phase HPLC (Agilent, 1200 Infinity) on a Phenomenex C-18 column (250 × 4.6 mm). The pH test was performed using a pH-meter (OHAUS, STARTER3100). Melting points were measured using a Mel-Temp apparatus and were not corrected. 1 H and 13 C NMR spectra were obtained using Bruker AV-300 or AV-600 spectrometers. Mass spectral analyses were performed on an API 4000 (ESI-HRMS).
Renilla luciferase was supplied by RayBiotech. ES-2-Rluc cells (a human ovarian cancer cell line stably expressing Renilla luciferase) were purchased from Shanghai BioDiagnosis Co., Ltd. Female nude mice (BALB/cA-nu) were purchased from the Animal Center of China Academy of Medical Sciences (Beijing, China). Luminescence imaging was recorded using an IVIS Kinetic (Caliper Life Sciences, USA) equipped with a cooled charge-coupled device (CCD) camera. Circular specified regions of interest (ROIs) were drawn over the areas, and the total flux was calculated using the Living Image software version 4.0 (Caliper Life Sciences).
Renilla luciferase was supplied by RayBiotech. ES-2-Rluc cells (a human ovarian cancer cell line stably expressing Renilla luciferase) were purchased from Shanghai BioDiagnosis Co., Ltd. Female nude mice (BALB/cA-nu) were purchased from the Animal Center of China Academy of Medical Sciences (Beijing, China). Luminescence imaging was recorded using an IVIS Kinetic (Caliper Life Sciences, USA) equipped with a cooled charge-coupled device (CCD) camera. Circular specified regions of interest (ROIs) were drawn over the areas, and the total flux was calculated using the Living Image software version 4.0 (Caliper Life Sciences).
7
Spectroscopic Analysis of Compounds
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NMR spectra were recorded on Bruker AV-500 and Bruker AV-600 spectrometers (Bruker, Bremen, Germany) with TMS as an internal standard and the peak signals of MeOD (δC/H 49.0/3.31) and CDCl3 (δC/H 77.16/7.26) as reference. The mass spectrometric (HRESIMS) data were acquired using an API QSTAR Pulsar mass spectrometer (Bruker, Bremen, Germany) and an AB SCIEX Trip TOF 5600+ mass spectrometer (SCIEX, Framingham, MA, USA). Optical rotations were measured with a JASCO P-1020 digital polarimeter (Jasco, Tokyo, Japan). IR spectra were recorded on a Shimadzu UV2550 spectrophotometer (Shimadzu, Kyoto, Japan). UV spectra and ECD data were collected using a JASCO J-715 spectropolarimeter (Jasco, Tokyo, Japan). Semipreparative HPLC was carried out using an ODS column (YMC-pack ODS-A, 10 × 250 mm, 5 µm, 4 mL/min, YMC, Kyoto, Japan). Column chromatography was carried out on silica gel (SiO2, 200–300 mesh, Qingdao Marine Chemical Inc., Qingdao, Shandong, China), and Sephadex LH-20 (green herbs, Beijing, China) and Rp-C18 (20–45 µm; Fuji Silysia Chemical Ltd., Durham, NC, USA) were used for column chromatography.
8
Synthesis and Characterization of 2-Aminoprop-1-ene-1,1,3-tricarbonitrile
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The solvents and reagents were purchased from commercial sources and used as received. 2-Aminoprop-1-ene-1,1,3-tricarbonitrile 2 was obtained from malononitrile according to the literature [24 (link)].
All melting points were measured with a Gallenkamp melting-point apparatus (Gallenkamp & Co., Ltd, London, UK) and were uncorrected. 1H and 13C-NMR spectra were recorded in DMSO-d6 with Bruker AM300, Bruker AV500, and Bruker AV600 spectrometers (Bruker Corporation, Billerica, MA, USA) at ambient temperature. Chemical shift values are relative to Me4Si. Two-dimensional (2D) NMR spectra were registered with a Bruker AV500 spectrometer. 1H NMR monitoring spectra were registered with a Bruker AM300 spectrometer (Bruker Corporation, Billerica, MA, USA). The IR spectrum was recorded with a Bruker ALPHA-T FT-IR spectrometer (Bruker Corporation, Billerica, MA, USA) in a KBr pellet. MS spectra (EI = 70 eV) were obtained directly with a Kratos MS-30 spectrometer (Kratos Analytical Ltd, Manchester, UK). High-resolution mass spectra (HRMS) were measured on a Bruker micrOTOF II (Bruker Corporation, Billerica, MA, USA) instrument using electrospray ionization (ESI).
All melting points were measured with a Gallenkamp melting-point apparatus (Gallenkamp & Co., Ltd, London, UK) and were uncorrected. 1H and 13C-NMR spectra were recorded in DMSO-d6 with Bruker AM300, Bruker AV500, and Bruker AV600 spectrometers (Bruker Corporation, Billerica, MA, USA) at ambient temperature. Chemical shift values are relative to Me4Si. Two-dimensional (2D) NMR spectra were registered with a Bruker AV500 spectrometer. 1H NMR monitoring spectra were registered with a Bruker AM300 spectrometer (Bruker Corporation, Billerica, MA, USA). The IR spectrum was recorded with a Bruker ALPHA-T FT-IR spectrometer (Bruker Corporation, Billerica, MA, USA) in a KBr pellet. MS spectra (EI = 70 eV) were obtained directly with a Kratos MS-30 spectrometer (Kratos Analytical Ltd, Manchester, UK). High-resolution mass spectra (HRMS) were measured on a Bruker micrOTOF II (Bruker Corporation, Billerica, MA, USA) instrument using electrospray ionization (ESI).
9
Untargeted Metabolite Analysis of Murine Colon
10
Synthesis and Characterization of Compounds 1 and 2
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Melting points were determined on an X4 apparatus (Beijing Tech Instrument Co. Ltd., Beijing, China) and were uncorrected. The 1H and 13C NMR spectra were recorded in CDCl3 on a Bruker AV-600 spectrometer at working frequencies of 600 and 150 MHz and a Bruker AV-300 spectrometer at working frequencies of 300 and 75 MHz, respectively. Chemical shifts are expressed in parts per million (δ) values and coupling constants (J) in Hertz. Infrared spectra were measured with a Thermo Scientific Nicolet IS-10 Spectrophotometer (Thermo Scientific, USA). HREIMS was measured on an Agilent 6210 TOFMS instrument (Agilent Technologies, USA). The cell proliferation assay was undertaken by a MTT method using 96-well plates on a MLLTISKAN MK3 analysis spectrometer (Thermo Scientific, Shanghai, China).
Compounds 1 (L1) and 2 (L2) were prepared according to the method of [21 (link)].
Compounds
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