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3 protocols using milli q direct ultrapure water system

1

Characterization of Organic Compounds

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High quality chemicals and reagents were purchased from standard sources such as Sigma-Aldrich (St. Louis, MO, USA) and VWR International (Radnor, PA, USA). Deionized water (18.2 Ω) used for making solutions was obtained from Milli-Q Direct Ultrapure Water System from Millipore (Billerica, MA, USA). All intermediates were characterized by proton nuclear magnetic resonance (1H NMR) and mass spectrometry (MS) analysis, and the purity of compounds was analyzed by high-performance liquid chromatography (HPLC). 1H NMR data were collected on a Bruker 400 MHz spectrometer (Bruker, Billerica, MA) using standard parameters, while chemical shifts are reported in ppm (δ) in reference to residual non-deuterated solvent. Electrospray ionization (ESI) MS analysis was performed on new compounds with an LTQ Orbitrap Elite system (ThermoFisher Scientific, Waltham, MA, USA) at the Mass Spectrometry and Biomarker Discovery Core facility of the Cedars-Sinai Medical Center, Los Angeles, CA.
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2

Analytical Characterization of CBD Oils

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Acetonitrile, methanol, and tert-butyl methyl ether (MTBE; HPLC-grade) were purchased
from Biosolve Chimie SARL (Dieuze, France). Formic acid (HPLC-grade)
and silver nitrate (analytical grade) were purchased from Fisher Scientific
(Loughborough, Leicestershire). Deionized water was obtained from
a Milli-Q Direct ultrapure water system (Millipore, USA). THC and
CBD standards were obtained from cannabis flowers and CBD oil, respectively.
According to nuclear magnetic resonance (NMR), thin layer chromatography
(TLC), and UHPLC-UV data (Supporting Information, Figures S1–S3), their purity was >98%. Chromatography
paper
was purchased from Hangzhou Special Paper Co., Ltd. (Hangzhou, China).
Different brands of pure CBD oils were purchased from health shops
(Wageningen, the Netherlands) or ordered online. Information on all
CBD oils is shown in the Supporting Information, Table S1. Ammonium acetate (analytical grade) was obtained from
Merck (Darmstadt, Germany). Santonin (analytical grade) was purchased
from Sigma (St. Louis, MO, USA).
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3

Synthesis and Characterization of DZ and DZ-SIM

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DZ and DZ-SIM were synthesized in our laboratory and dissolved in dimethylsulfoxide (DMSO) at a concentration of 20 mM and stored at −20°C. Cisplatin, SIM, Gefitinib, Icotinib, and AZD9291 were purchased from MedKoo Biosciences (Morrisville, NC). Annexin V and propidium iodide (PI) were purchased from Biolegend (San Diego, CA). MitoSOX, MitoTracker, LysoTracker, and JC-1 were purchased from ThermoFisher. For the work of chemical synthesis, all chemicals and reagents were purchased from Sigma-Aldrich (St. Louis, MO) and/or ThermoFisher Scientific and used as is since the products derived them were purified and analyzed afterwards. Deionized distilled ultrapure water with resistivity of 18.2 MΩ cm used for making solutions was obtained from Milli-Q Direct Ultrapure Water System from Millipore (Billerica, MA, USA). 1H-NMR data were collected on Bruker 400 MHz spectrometers using standard parameters, chemical shifts are reported in ppm (δ) in reference to residual non-deuterated solvent. Electrospray ionization mass spectrometry (ESI-MS) analysis was performed on new compounds at Cedar-Sinai’s Proteomics & Metabolomics Core using an LTQ Orbitrap Elite mass spectrometer.
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