Cell culture essentials, including DMEM (Dulbecco’s Modified Eagle Medium), sodium pyruvate, non-essential amino acids, fetal bovine serum (FBS), and penicillin/streptomycin antibiotic mixture, were obtained from GIBCO (Grand Island, NY, USA). Diallyl trisulfide (DATS, purity > 98%) was procured from LKT Laboratories (St. Paul, MN, USA), and RNase A was sourced from Promega (Madison, WI, USA). Cyclin B1, Cdk1, pERK1/2, ERK1 antibodies were purchased from Santa Cruz Biotechnology (Santa Cruz, CA, USA); the anti-beta actin antibody was purchased from Sigma (St. Louis, MO, USA); and the antibody against cleaved poly-(ADP-ribose)-polymerase (c-PARP), cleaved caspase-3, pAkt (Ser 473), Akt, γH2AX (Ser 139), were purchased from Cell Signaling Technology (Danvers, MA, USA). UMSCC-22A, UMSCC-22B, and Cal33 cells were a generous gift from Prof. Daniel E. Johnson (University of California, San Francisco, CA, USA). HNSCC cells were grown in DMEM and supplemented with 10% FBS, 100 µg/mL streptomycin, and 100 units/mL penicillin under standard culture conditions. Stock solution of DATS was prepared in dimethyl sulfoxide (DMSO).
Diallyl trisulfide
Manufactured by LKT Laboratories
Sourced in United States
Diallyl trisulfide is a chemical compound that is a component of garlic oil. It is a clear, colorless to pale yellow liquid with a characteristic garlic odor. Diallyl trisulfide has a molecular formula of C6H10S3 and a molar mass of 182.32 g/mol.
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Lab products found in correlation
Diallyl sulfide, by Merck Group (2 mentions)
Cyclin b1, by Santa Cruz Biotechnology (1 mentions)
Non essential amino acids (neaa), by Thermo Fisher Scientific (1 mentions)
Penicillin streptomycin antibiotic mixture, by Thermo Fisher Scientific (1 mentions)
Rnase a, by Promega (1 mentions)
P erk1 2, by Santa Cruz Biotechnology (1 mentions)
Anti β actin antibody, by Merck Group (1 mentions)
Dulbecco modified eagle medium (dmem), by Thermo Fisher Scientific (1 mentions)
Fetal bovine serum (fbs), by Thermo Fisher Scientific (1 mentions)
Allyl methyl sulfide, by Merck Group (1 mentions)
Quercetin, by Fujifilm (1 mentions)
Eugenol, by Fujifilm (1 mentions)
Capsaicin, by Fujifilm (1 mentions)
Cinnamaldehyde, by Fujifilm (1 mentions)
Naaso2, by Fujifilm (1 mentions)
Sulforaphane, by LKT Laboratories (1 mentions)
6 gingerol, by Fujifilm (1 mentions)
Mili q water, by Merck Group (1 mentions)
Curcumin, by Merck Group (1 mentions)
Naaso2, by Merck Group (1 mentions)
6 protocols using diallyl trisulfide
1
DATS Inhibits HNSCC Cell Growth
2
Quantification of Garlic Organosulfur Compounds
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l (+)- and l (±)-S-allylcysteine sulfoxides (natural and racemic alliin), S-allylcysteine, diallyl disulfide, and diallyl trisulfide (each ≥98%) were purchased from LKT Laboratories, Inc. (St. Paul, MN, USA). Allyl methyl sulfide and diallyl sulfide (each 99%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). γ-Glutamyl-S-allylcysteine (99%) was purchased from U.S. Pharmacopeia (Rockville, MD, USA). Allicin (98%) was prepared by oxidation of diallyl disulfide with hydrogen peroxide, followed by purification, as previously described [30 (link)]. Its concentration was validated with a second allicin standard prepared from alliin and crude alliinase [29 ]. Allyl methyl thiosulfinates, allyl-1-propenyl thiosulfinates, diallyl tetrasulfide, allyl methyl disulfide, allyl methyl trisulfide, and allyl methyl tetrasulfide were identified and quantified based on their relative retention times and relative extinction coefficients, compared to allicin and diallyl trisulfide, as previously described [19 (link),21 (link)].
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3
Zebrafish Nrf2 Mutant Model Analysis
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In this study, wild-type (AB strain) and Nrf2-mutant (nfe2l2afh318) [15 (link)] zebrafish larvae were used. The Nrf2-mutant line was maintained by polymerase chain reaction based genotyping, as described previously [28 (link)]. Embryos were obtained by natural mating. Capsaicin, carnosic acid, cinnamaldehyde, eugenol, 6-gingerol, isoeugenol, quercetin, H2O2 and NaAsO2 were purchased from FUJIFILM Wako (Osaka, Japan). Diallyl trisulfide and sulforaphane were bought from LKT Laboratories (St. Paul, MN, USA). Curcumin and 6-MSITC were purchased from Sigma-Aldrich Japan (Tokyo, Japan) and Abcam (Cambridge, UK), respectively. H2O2 and NaAsO2 were dissolved in MiliQ water (Merck-Millipore, Billerica, MA), sulforaphane in ethanol and other phytochemicals were dissolved in dimethyl sulfoxide for the stock solution, and were diluted to the final concentration with E3+ medium (5 mM NaCl, 0.17 mM KCl, 0.33 mM CaCl2, 0.33 mM MgSO4 and 0.1 μg/mL methylene blue).
4
Diallyl Trisulfide Protects Cardiomyocytes
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Diallyl trisulfide was purchased from LKT Laboratories (St. Paul, MN, USA). Streptozotocin (STZ), 4’, 6-diamino-2-phenylindole (DAPI) and Compound C (Com.C) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Sodium pentobarbital, Evans blue (EB) and triphenyltetrazolium chloride (TTC) were purchased from Solarbio Life Sciences (Beijing, China). 2-methoxyestradiol (2ME) was purchased from Selleck Chemicals (Houston, TX, USA). LY294002 and BCA Protein Assay Kit were purchased from Beyotime Biotechnology (Shanghai, China). Terminal deoxynucleotidyltransferase-mediated dUTP nick end labeling (TUNEL) assay kit was purchased from Roche (Mannheim, Germany). H9c2 cardiomyoblasts were obtained from Tiancheng biotechnology (Shanghai, China). The primary antibodies against p-AMPK (Thr172), AMPK, cleaved caspase-3, Bcl-2 and Bax were obtained from Cell Signaling Technology (Boston, MA, USA). The primary antibodies against p-ACC (Ser79), ACC, p-AKT (Thr308), AKT, p-GSK3β (Ser9), GSK3β, HIF-1α and β-actin were purchased from Santa Cruz Biotechnology (Dallas, TX, USA). The secondary antibodies were purchased from the Zhongshan Company (Beijing, China).
5
Diallyl Trisulfide Protocol
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Diallyl trisulfide was purchased from LKT Laboratories (St. Paul, MN, USA), and it was dissolved in dimethyl sulphoxide (DMSO; Sigma-Aldrich Corp., St. Louis, MO, USA). All antibodies were purchased from Santa Cruz Biotechnology, Inc. (Santa Cruz, CA, USA).
6
Synthesis and Purification of Garlic Organosulfur Compounds
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Diallyl sulfide (DAS; 97%), diallyl disulfide (DADS; 80%), porcine pepsin (P7000), porcine pancreatin (P7545) and porcine bile salts (B8756) were purchased from Sigma-Aldrich (Saint Louis, USA). Diallyl trisulfide (DATS; 98%) was purchased from LKT Laboratories, Inc (St. Paul, MN, USA). Acetonitrile (ACN) chromatographic grade was purchased from J.T.Baker (USA). Methanol (MeOH), and dichloromethane (DCM) chromatographic grade were purchased from Merck (Kenilworth, NJ, USA). Ultrapure water (18 MΩcm) was obtained from a Milli-Q water purification system (Millipore, Molsheim, France). Allicin was synthesized by oxidation of DADS (Ramírez, Locatelli, Torres-Palazzolo, Altamirano, & Camargo, 2017 (link)). E/Z ajoene was obtained by heating and stirring of allicin in acetone/water (40:60, v/v) (Ramírez, Locatelli, Torres-Palazzolo et al., 2017) (link). 2-vinyl-4H-1,3-dithiine was synthesized by heating allicin in acetone/methanol (60:40, v/v) following the procedure described by Iberl, Winkler, & Knobloch, 1990 with slight modifications. All synthesized compounds were properly purified and quantified as described in previous work (Ramírez, Locatelli, Torres-Palazzolo et al., 2017) (link).
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