All reagents used for chemical synthesis were purchased from commercially available sources (Sigma Aldrich U.S. or Fisher Scientific U.S.) and used without further purification. Flash chromatography was performed using 60 Å mesh standard grade silica gel from Sorbtech. NMR solvents were obtained from Cambridge Isotope Laboratories and used as is. All 1H NMR (400 MHz) and 13C NMR (400 MHz) spectra were recorded at 25 °C on a Varian Mercury spectrometer. Chemical shifts (δ) are given in parts per million relative to the respective NMR solvent; coupling constants (J) are in hertz (Hz). Abbreviations used are s, singlet; bs, broad singlet; d, doublet; dd, doublet of doublets; t, triplet; dt, doublet of triplets; m, multiplet. Mass spectra were obtained at the NCSU Department of Chemistry Mass Spectrometry Facility. The purities of the tested compounds were all verified to be >95% by LC-MS analysis on a Shimadzu LC-MS 2020 with Kinetex, 2.6 mm, C18 50 × 2.10 mm.
Mercury spectrometer
Manufactured by Agilent Technologies
Sourced in China, United States
The Mercury spectrometer is a laboratory instrument designed to detect and analyze the presence of mercury in various samples. It utilizes advanced spectroscopic techniques to precisely measure the concentration of mercury in a sample.
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Lab products found in correlation
Prep 1200 series, by Agilent Technologies (5 mentions)
1200 series system, by Agilent Technologies (4 mentions)
Drx 600 spectrometer, by Agilent Technologies (4 mentions)
G1969a api tof, by Agilent Technologies (4 mentions)
Orbitrap elite, by Thermo Fisher Scientific (2 mentions)
Luna 75, by Phenomenex (2 mentions)
Deuterated solvent, by Cambridge Isotopes (2 mentions)
N acetyl l cysteine, by Solarbio (1 mentions)
Carbonyl cyanide m chlorophenyl hydrazine, by Solarbio (1 mentions)
Dcfh da, by Merck Group (1 mentions)
Methyl thiazolyl tetrazolium (mtt), by Merck Group (1 mentions)
2767 sample manager system, by Waters Corporation (1 mentions)
Polyvinylidine fluoride membrane, by Merck Group (1 mentions)
Antioxidant enzyme assay kits, by Nanjing Jiancheng (1 mentions)
Centricon ym 3, by Merck Group (1 mentions)
Rf 5301 spectrofluorimeter, by Shimadzu (1 mentions)
Lambda 25 spectrophotometer, by PerkinElmer (1 mentions)
Bca protein assay kit, by Beyotime (1 mentions)
1100 series hplc, by Agilent Technologies (1 mentions)
C18 guard column, by Phenomenex (1 mentions)
25 protocols using mercury spectrometer
1
Organic Synthesis Protocols and Purification Techniques
2
Characterization of Cellular Oxidative Stress
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Dulbecco’s modified Eagle medium (DMEM) and fetal bovine serum (FBS) were purchased from Hyclone (Shanghai, China). DCFH-DA (2′, 7′-dichlorodi-hydrofluoresceindiacetate) and MTT (3-[4, 5-dimethylthiazol-2-yl]-2, 5-diphenyltetrazolium bromide) were obtained from Sigma (Beijing, China).
All antibodies were obtained from Affinity Biosciences (Changzhou, China). DAPI (4DCFH-DA [2′, 7′-dichlorodi-hydrofluoresceindiacetate],6-diamidino-2-phenylindole), N-acetyl-L-cysteine (NAC) and carbonyl cyanide m-chlorophenyl hydrazine (CCCP) were obtained from Beijing Solarbio Science & Technology Co., Ltd. Varian Mercury spectrometer operating at 400 MHz for 1H NMR and 100 MHz for 13C NMR was used to record the 1H NMR and 13C NMR spectra, and Orbitrap Elite (Thermo Scientific) mass spectrometer Bruker APEX II 47e mass spectrometer was applied to determine the ESI/HRMS spectra.
All antibodies were obtained from Affinity Biosciences (Changzhou, China). DAPI (4DCFH-DA [2′, 7′-dichlorodi-hydrofluoresceindiacetate],6-diamidino-2-phenylindole), N-acetyl-L-cysteine (NAC) and carbonyl cyanide m-chlorophenyl hydrazine (CCCP) were obtained from Beijing Solarbio Science & Technology Co., Ltd. Varian Mercury spectrometer operating at 400 MHz for 1H NMR and 100 MHz for 13C NMR was used to record the 1H NMR and 13C NMR spectra, and Orbitrap Elite (Thermo Scientific) mass spectrometer Bruker APEX II 47e mass spectrometer was applied to determine the ESI/HRMS spectra.
3
HPLC-MS and NMR Analysis of Compounds
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The mass spectra were obtained by injecting the samples into a high-performance liquid chromatograph with a diode array detector coupled with a low resolution electrospray ionization mass spectrometer (HPLC-DAD-ESI-MS; 2767 Sample Manager System, Waters, Milford, Massachusetts) and a quadrupolar analyzer ion trap (trap ions) operating in the positive mode. The 1H and 13C NMR spectra (500 and 125 MHz, acetone-d6) (1D and 2D) were recorded on a Varian Mercury spectrometer using TMS as the internal standard.
4
Antioxidant Enzyme Activity Assay
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All reagents and PRMI 1640 media were obtained from Sigma–Aldrich Ltd. (Beijing, China) or J&K Scientific Ltd. (Beijing, China). Antioxidant enzyme assay kits were purchased from Nanjing Jiancheng Bioengineering Institute (Nanjing, China). The BCA protein assay kit was obtained from Beyotime Institute of Biotechnology (Jiangsu, China). Polyvinylidine fluoride membranes and Centricon YM-3 were purchased from the Millipore Corp. (USA). Rabbit anti-cyt c (AF0146) and rabbit anti-VDAC1 (DF6140) were obtained from Affinity Biosciences (OH, USA). Fetal bovine serum was purchased from Hangzhou Sijiqing Biomaterials Co., Ltd. (Hangzhou, China).
1H NMR and 13C NMR spectra were recorded using a Varian Mercury spectrometer operating at 400 MHz for 1H NMR and 100 MHz for 13C NMR. HR-MS spectra were obtained on an Orbitrap Elite (Thermo Scientific) mass spectrometer. UV/Vis spectra were recorded at 25 °C with a Perkin-Elmer Lambda 25 spectrophotometer that was equipped with temperature-controlled cell holders (USA). Fluorescence intensity and fluorescence spectra were measured at 25 °C with an Infinite M200 Pro Multimode Reader (Switzerland) and a Shimadzu RF-5301 spectrofluorimeter (Japan), respectively.
1H NMR and 13C NMR spectra were recorded using a Varian Mercury spectrometer operating at 400 MHz for 1H NMR and 100 MHz for 13C NMR. HR-MS spectra were obtained on an Orbitrap Elite (Thermo Scientific) mass spectrometer. UV/Vis spectra were recorded at 25 °C with a Perkin-Elmer Lambda 25 spectrophotometer that was equipped with temperature-controlled cell holders (USA). Fluorescence intensity and fluorescence spectra were measured at 25 °C with an Infinite M200 Pro Multimode Reader (Switzerland) and a Shimadzu RF-5301 spectrofluorimeter (Japan), respectively.
5
Analytical Characterization of Compounds
6
Characterization of Ruthenium(II) Bipyridine Complex
7
Purification and Characterization of Organic Compounds
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Reagents were used as purchased without further purification. Solvents for synthesis (dichloromethane and acetonitrile) were dried and freshly distilled before use according to procedures described in the literature. TLC was performed on pre-coated silica gel polyester plates (0.25 mm thickness) with a UV fluorescence indicator 254 (Polychrome SI F254). Chromatographic purification was performed on silica gel columns by flash (Kieselgel 40, 0.040–0.063; Merck) chromatography. Melting point was determined on a Büchi 510. 1H NMR and 13C NMR spectra were recorded in CDCl3 or DMSO‑d6 on a Varian Mercury spectrometer operating at 400/100 MHz. Chemical shifts (δ) are given in ppm downfield from tetramethylsilane and coupling constants (J values) are in Hertz. IR spectra were run on a Nicolet Impact 410 Spectrophotometer. For FAB-HRMS analyses, a VG-TS250 apparatus (70 eV) was used.
8
Characterization of Organic Compounds
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1H and 13C NMR spectra were acquired on a Varian 400 MHz, Varian Mercury spectrometer at 400 MHz for 1H and 100 MHz for 13C. TLC were performed on glass TLC plates, silica gel coated with fluorescent indicator F254 (thickness of 200 μm). Preparative TLC were performed on PTLC glass plates with fluorescent indicator F254 (thickness of 1 mm). Column chromatography was performed using 230–400 mesh silica gel. All chemical reagents and solvents were purchased from commercial sources and used without further purification. CH2Cl2 was dried by distillation over CaH2. The purity of the final compounds was determined by NMR spectroscopy and elemental analysis and was in agreement with the proposed structures with purity ≥95%.
9
Characterization of Alcohols and Carbamates
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Melting points were determined using the Buchi Melting Point B-450 and were left uncorrected. NMR spectra were recorded using a Varian Mercury spectrometer, with 1H at 300.060 MHz and 13C at 75.475 MHz (Supplementary Materials, Figures S1–S4 ). Proton chemical shifts were referenced using the TMS internal standard. Chemical shifts are reported in parts per million (ppm, δ units). Coupling constants are reported in Hertz (Hz) units. Splitting patterns are designed as s, singlet; d, doublet; t, triplet; q, quartet; dd, double doublet; m, multiple; and b, broad. All commercial chemicals and solvents were of a reagent grade and were purchased from Merck (Merck, Darmstadt, Germany). They were used without further purification unless otherwise specified. The reactions were monitored by thin-layer chromatography on silica gel plates (60F-254, Merck), and the analysis of the plates was carried out using a UV lamp (254/365 nm). Flash chromatography was performed on silica gel 60 (Merck). Elemental analyses of C, H and N were recorded on a Perkin-Elmer 240 B microanalyzer (PerkinElmer, Waltham, MA, USA), obtaining analytical results within ± 0.4% of the theoretical values for all the compounds. The purity of all the compounds was over 98%. The chemical synthesis and characterization of alcohols 1–6 and carbamates 7–28 were previously reported by us [19 (link)].
10
Purification and Characterization of Organic Compounds
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HPLC spectra for all compounds were acquired using an Agilent 1200 Series system with DAD detector. Chromatography was performed on a 2.1×150 mm Zorbax 300SB-C18 5 μm column with water containing 0.1% formic acid as solvent A and acetonitrile containing 0.1% formic acid as solvent B at a flow rate of 0.4 mL/min. The gradient program was as follows: 1% B (0–1 min), 1–99% B (1–4 min), and 99% B (4–8 min). High-resolution mass spectra (HRMS) data were acquired in positive ion mode using an Agilent G1969A API-TOF with an electrospray ionization (ESI) source. Nuclear Magnetic Resonance (NMR) spectra were acquired on a Bruker DRX-600 spectrometer (600 MHz 1H, 150 MHz 13C) or a Varian Mercury spectrometer (400 MHz 1H, 100 MHz 13C). Chemical shifts are reported in ppm (δ). Preparative HPLC was performed on Agilent Prep 1200 series with UV detector set to 254 nm. Samples were injected into a Phenomenex Luna 75 x 30 mm, 5 μm, C18 column at room temperature. The flow rate was 40 mL/min. A linear gradient was used with 10% (or 50%) of MeOH (A) in H2O (with 0.1 % TFA) (B) to 100% of MeOH (A). HPLC was used to establish the purity of target compounds. All final compounds had > 95% purity using the HPLC methods described above.
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