ST-246 and 2-hydroxy-N-{3,5-dioxo-4-azatetracyclo[5.3.2.02.6.08.10]dodec-11-en-4-yl}-5-methylbenzamide (IS) were synthetized for research proposes with yield >96% and kindly provided by A.Ya. Tikhonov and B.A. Selivanov (N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Russia). LC-MS grade acetonitrile was purchased from Biosolve (Dieuze, France). Methanol of HPLC grade was obtained from J. T. Baker (Gliwice, Poland). HPLC grade water for the experiments was produced with a Milli-Q purification system from Millipore Corp. (Bedford, MA, USA). LC-MS grade formic acid was acquired from Sigma-Aldrich (St. Louis, MO, USA). Human plasma was obtained from healthy volunteers with approval by the Human Ethics Committee of the Institute of Chemical Biology and Fundamental Medicine (protocol code 10 of 26 December 2019). The volunteers consisted of people aged 18 years or older with the following inclusion criteria: had no contraindications, were healthy, and had not taken other medications within the last 7 days. Blood sampling from the cubital vein was performed in the morning on an empty stomach after at least 12 h of fasting in 4 mL vacutainer plasma separation tubes. Blood plasma was obtained according to the standard method by centrifugation at 1500× g for 10 min using a refrigerated centrifuge at 4 °C.
Acetonitrile lc ms grade
Manufactured by Biosolve
Sourced in France
Acetonitrile (LC-MS grade) is a high-purity organic solvent commonly used as a mobile phase component in liquid chromatography-mass spectrometry (LC-MS) applications. It is a colorless, volatile liquid with a characteristic odor. Acetonitrile (LC-MS grade) is designed to meet the stringent requirements of LC-MS analysis, ensuring low levels of impurities and contaminants that could interfere with sensitive mass spectrometric detection.
Automatically generated - may contain errors
Lab products found in correlation
Formic acid, by Merck Group (7 mentions)
Hydrochloric acid (hcl), by Merck Group (5 mentions)
Methanol, by Biosolve (4 mentions)
Sodium hydroxide (naoh), by Merck Group (4 mentions)
Formic acid, by Biosolve (3 mentions)
Lc ms grade water, by Biosolve (3 mentions)
Ammonium formate, by Merck Group (3 mentions)
Propionic anhydride, by Merck Group (2 mentions)
Ammonium acetate, by Biosolve (2 mentions)
Ammonium hydroxide solution, by Merck Group (2 mentions)
In house purification system, by Merck Group (2 mentions)
Dipotassium hydrogen phosphate, by Merck Group (2 mentions)
Isopropanol, by Biosolve (2 mentions)
Diethyl ether, by Biosolve (2 mentions)
Thiophenol, by Merck Group (2 mentions)
Heptane, by Biosolve (2 mentions)
2 1h benzotriazol 1 yl 1 1 3 3 tetramethyluronium fluorophosphate hbtu, by Iris Biotech (2 mentions)
N fmoc protected amino acids, by Iris Biotech (2 mentions)
Acetonitrile, by Biosolve (2 mentions)
Procyanidin b3, by Phytolab (2 mentions)
22 protocols using acetonitrile lc ms grade
1
Synthesis and Characterization of ST-246 and IS Compounds
2
Quantification of Catecholamines and Metabolites
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LC-MS grade acetonitrile, isopropanol, methanol,
formic acid, and ammonium acetate were purchased from Biosolve BV
(Valkenswaard, The Netherlands). Glutathione (reduced), ascorbic acid,
dipotassium hydrogen phosphate, pyridine, and hydrochloric acid (32%)
were from Merck Millipore (Darmstadt, Germany). Ammonium hydroxide
solution (28–30%), propionic anhydride, K2EDTA dihydrate,l -DOPA, dopamine-HCl, norepinephrine, epinephrine, 3-methoxytyramine, dl -metanephrine-HCl, dl -normetanephrine-HCl, and l -DOPA-d3, all of analytical purity,
were purchased from Sigma-Aldrich (MI, USA). Stable deuterated isotopes
for dopamine-d4-HCl, norepinephrine-d6-HCl, and epinephrine-d3 were from CDN Isotopes (Pointe-Claire, Canada), 3-methoxytyramine-d4-HCl anddl -metanephrine-d3-HCl from Cambridge Isotopes (MA, USA), and dl -normetanephrine-d3-HCl from Medical
Isotopes (NH, USA). Ultrapure water was produced using an in-house
purification system (Merck Millipore, MA, USA).
formic acid, and ammonium acetate were purchased from Biosolve BV
(Valkenswaard, The Netherlands). Glutathione (reduced), ascorbic acid,
dipotassium hydrogen phosphate, pyridine, and hydrochloric acid (32%)
were from Merck Millipore (Darmstadt, Germany). Ammonium hydroxide
solution (28–30%), propionic anhydride, K2EDTA dihydrate,
were purchased from Sigma-Aldrich (MI, USA). Stable deuterated isotopes
for dopamine-d4-HCl, norepinephrine-d6-HCl, and epinephrine-d3 were from CDN Isotopes (Pointe-Claire, Canada), 3-methoxytyramine-d4-HCl and
Isotopes (NH, USA). Ultrapure water was produced using an in-house
purification system (Merck Millipore, MA, USA).
3
Peptide Synthesis with HBTU and Fmoc-Protected Amino Acids
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2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium fluorophosphate (HBTU) and N-Fmoc protected amino acids were obtained from Iris Biotech GmbH. 4-Mercaptophenylacetic acid (97%, MPAA), 3-mercaptopropionic acid (MPA), tris(2-carboxyethyl)phosphine hydrochloride (≥98%, TCEP), thiophenol, triisopropylsilane (TIS), guanidine hydrochloride (≥99%), sodium phosphate dibasic dihydrate (≥99%), hydrochloric acid (reagent grade, 37%), and sodium hydroxide (pellets, 97%) were purchased from Sigma-Aldrich. All other reagents were purchased from Acros Organics or Merck and were of the purest grade available. Peptide synthesis grade N,N-dimethylformamide, dichloromethane, diethylether, acetonitrile, heptane, LC–MS-grade acetonitrile (0.1% TFA), LC–MS-grade water (0.1% TFA), N,N-diisopropylethylamine (DIEA), and acetic anhydride were purchased from Biosolve and Fisher-Chemical. Trifluoroacetic acid (TFA) was obtained from Biosolve. Decane (synthesis grade) was purchased from Merck. Solvents and reagents were used as received. Water was purified with a Milli-Q UltraPure Water Purification System.
4
Quantification of Polyphenol Standards
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Standards of (+)-catechin, (−)-epicatechin, procyanidin dimer A2, protocatechuic acid, and 3-O-caffeoylquinic acid were purchased from Sigma-Aldrich (Steinheim, Germany), procyanidin B2 was purchased from Extrasynthese (Genay, France), procyanidin B3, and quercetin-3-O-glucoside were acquired from Phytolab (Vestenbergsgreuth, Germany), and procyanidin B5 was acquired from TransMIT PlantMetaChem (Giessen, Germany). LC−MS-grade acetonitrile and LC−MS-grade formic acid were from Biosolve (Valkenswaard, The Netherlands) and purified water was obtained from a Milli-Q water Millipore system (Bedford, MA, USA).
5
Solid-Phase Peptide Synthesis Reagents
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1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium fluorophosphate (HBTU) and N-Fmoc-protected amino acids were obtained from Iris Biotech GmbH. Piperidine, diisopropylcarbodiimide (DIC), N-hydroxybenzotriazole (HOBt), MPAA (97%, MPAA), 3-mercaptopropionic acid (MPA), tris(2-carboxyethyl)phosphine hydrochloride (≥98%, TCEP·HCl), thiophenol, triisopropylsilane (TIS), guanidine hydrochloride (≥99%, Gn·HCl), hydrochloric acid (reagent grade, 37%), and sodium hydroxide (pellets, 97%) as well as other reagents were purchased from Sigma Aldrich, Acros Organics or Merck and were of the purest grade available. Peptide synthesis grade N,N-dimethylformamide (DMF), dichloromethane, diethyl ether, acetonitrile, heptane, LC-MS-grade acetonitrile (0.1% TFA), LC-MS grade water (0.1% TFA), N,N-diisopropylethylamine (DIEA), acetic anhydride (Ac2O), and trifluoroacetic acid (TFA) were purchased from Biosolve and Fisher-Chemical. NovaSyn TGR solid support was purchased from Sigma Aldrich. Bis(2-sulfenylethyl)amino trityl 1% divinylbenzene cross-linked polystyrene solid support (SEA PS) was produced on demand by Roowin. Solvents and reagents were used as received.
6
Quantification of Catechins and Procyanidins
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Standards of (+)-catechin (≥98%) and (−)-epicatechin (≥90%) were purchased from Sigma-Aldrich (Steinheim, Germany), procyanidin B1 (≥90%) and procyanidin B2 (≥90%) were purchased from Extrasynthese (Genay, France), procyanidin B3 (≥99%) was acquired from Phytolab (Vestenbergsgreuth, Germany) and procyanidin B4 (≥95%) and procyanidin B5 (≥95%) were acquired from TransMIT PlantMetaChem (Giessen, Germany), and L-ascorbic acid from Sigma-Aldrich (Steinheim, Germany). LC−MS-grade acetonitrile, LC−MS-grade methanol (MeOH), LC−MS-grade formic acid, from Biosolve (Valkenswaard, The Netherlands) and purified water obtained from a Milli-Q water Millipore system (Bedford, MA, USA) were used for the UPLC runs. A total of 500 mg Sep-Pak C18 solid phase extraction (SPE) cartridges were purchased from Waters Corporation (Milford, MA, USA). Reference compounds or fractions N1 to N8 were used (Figure 1 ).
7
Quantification of L-allysine and Pipecolic Acid
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L-allysine ethylene acetal (AEA) (>98%), Amberlyst 15 hydrogen form, and pipecolic acid (PA) (99%) were purchased from Sigma-Aldrich (St. Louis, US). DL-pipecolic acid-d9 (internal standard) was purchased from Toronto Research Chemicals (Ontario, Canada). LC-MS grade acetonitrile was purchased from Biosolve Chimie SARL (Dieuze, France). Formic acid, 85% (AR grade), was purchased from Merck (Kenilworth, US). In-house Milli Q water (Siemens Ultra Clear) was used. iHILIC fusion (+) column (100 × 2.1 mm, 3.5 μm) was purchased from HILLICON AB (Umea, Sweden).
8
Quantitative LC-MS Analysis of Neurotransmitters
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LC-MS-grade acetonitrile, isopropanol, methanol, formic acid, and ammonium acetate were purchased from Biosolve. Ascorbic acid, dipotassium hydrogen phosphate, acetic acid (99%), and hydrochloric acid (32%) were obtained from Merck Millipore. Ammonium hydroxide solution (28%-30%), propionic anhydride, dipotassium EDTA dihydrate, glutathione (reduced), tryp- tophan, 5-HTP, serotonin, and 5-HIAA, all of analytical purity, were purchased from Sigma Aldrich. Ultrapure water was produced with an in-house purification system (Merck Millipore). Stable deuterated isotopes for tryptophan-d5, serotonin-d4 creatinine sulfate, and 5-HIAA-d2 were purchased from CDN Isotopes; 5-HTP-d4, from Toronto Research Chemicals.
9
Quantification of Metabolites in Biological Samples
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The standards and internal standards TRP, KYN, 5-HTP, 5-HT, 5-HIAA, and 5-HT-d4 were purchased from Sigma-Aldrich (Saint Louis, Missouri, USA). TRP-d5 and 5-HIAA- 13 C 6 were from Cambridge Isotope Laboratories (Tewksbury, Massachusetts, USA), 5-HTP-d4 from Toronto Research Chemicals (Toronto, Ontario, Canada), and KYN-d4 from Buchem B.V. (Apeldoorn, the Netherlands). LC-MS grade acetonitrile, formic acid, and methanol were purchased from Biosolve B.V. (Valkenswaard, the Netherlands), and the ultra-pure water was delivered in house by the Q-POD Ultrapure Remote Dispenser (Merck Millipore).
10
Solubility Enhancement of NSAIDs
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Ketoprofen, ketorolac, indoprofen, fenoprofen, suprofen, ibuprofen, S-ibuprofen, flurbiprofen, benzoic acid, naphthalene, and uracil standard were purchased from Sigma-Aldrich (St. Louis, MO, USA). Naproxen reference standard was kindly provided by Temad faculty (Tehran, Iran).
The chemical structures of solutes have been summarized in Fig. 1S. Some chemical and physical properties of tested solutes are collected in table 1. Hp-β-CD with the substitution degree of 3.5-5.5 was obtained from Cyclodextrin-Shop (Tilburg, Netherlands). Purified water from a Milli-Q reagent water system (Millipore, Bedford, MA, USA) was used to prepare the buffer and reagent solutions. The analytical grade H3PO4, NaH2PO4, NaOH were purchased from Merck (Darmstadt, Germany). LC/MS grade acetonitrile, ethanol and methanol were also purchased from Biosolve (Valkenswaard, Netherland).
The chemical structures of solutes have been summarized in Fig. 1S. Some chemical and physical properties of tested solutes are collected in table 1. Hp-β-CD with the substitution degree of 3.5-5.5 was obtained from Cyclodextrin-Shop (Tilburg, Netherlands). Purified water from a Milli-Q reagent water system (Millipore, Bedford, MA, USA) was used to prepare the buffer and reagent solutions. The analytical grade H3PO4, NaH2PO4, NaOH were purchased from Merck (Darmstadt, Germany). LC/MS grade acetonitrile, ethanol and methanol were also purchased from Biosolve (Valkenswaard, Netherland).
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