Nicotine hydrogen tartrate, tyramine HCl, anabasine, myosmine, harmane, and norharmane were purchased from Sigma-Aldrich (St. Louis, MO, USA). D, L Nornicotine was purchased from Matrix Scientific (Columbia, SC, USA), and D,L anatabine was purchased from Fisher Scientific (Pittsburgh, PA, USA). Nicotine, nornicotine, tyramine HCl, myosmine, anabasine and anatabine were dissolved in 0.9% sterile saline (Hospira Inc, Lake Forest, IL, USA). harmane and norharmane were both dissolved in a solution containing equal parts sterile saline and DMSO (Sigma-Aldrich), which also served as the vehicle for these two compounds. All tobacco constituent solutions were injected (s.c.) in a volume of 1.0 ml/kg body weight.
Norharmane
Manufactured by Merck Group
Sourced in United States, Germany
Norharmane is a laboratory reagent produced by Merck Group. It is a heterocyclic organic compound that can be used in various scientific applications. No further details about its intended use or applications are provided.
Automatically generated - may contain errors
Lab products found in correlation
Harmane, by Merck Group (7 mentions)
Harmine, by Merck Group (4 mentions)
Chloroform, by Merck Group (3 mentions)
Harmaline, by Merck Group (3 mentions)
Milli q water purification system, by Merck Group (3 mentions)
Harmalol hydrochloride dihydrate, by Merck Group (3 mentions)
Harmol hydrochloride dihydrate, by Merck Group (3 mentions)
2 5 dihydroxybenzoic acid, by Merck Group (2 mentions)
Ammonium formate, by Merck Group (2 mentions)
Formic acid, by Merck Group (2 mentions)
Acetic acid, by Merck Group (2 mentions)
Myosmine, by Merck Group (1 mentions)
Anabasine, by Merck Group (1 mentions)
Tyramine hcl, by Merck Group (1 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (1 mentions)
Nicotine hydrogen tartrate, by Merck Group (1 mentions)
Q exactive orbitrap, by Thermo Fisher Scientific (1 mentions)
Glass microscope slide, by Avantor (1 mentions)
Theophylline, by Merck Group (1 mentions)
Bovine serum albumin (bsa), by Yeasen (1 mentions)
24 protocols using norharmane
1
Tobacco Constituents Bioavailability Protocol
2
MALDI-MS Imaging of Liver Lipids
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Ten-μm frozen liver sections were placed on glass microscope slides (VWR) using a cryostat. Adjacent sections were stained with H&E (Sigma Aldrich). Matrix solution (5 mg/ml) of norharmane (Sigma‐Aldrich, St. Louis, MO) was prepared in 2:1:0.8 methanol:chloroform:water (v/v) and administered to the tissue surface using a SMALDIPrep sprayer (TransMIT GmbH, Giessen, Germany). Imaging experiments were performed using an AP-SMALDI10 source (TransMIT GmbH) coupled to an Orbitrap Q-Exactive (Thermo Fisher Scientific) at 10 μm increments across the tissue, using 2D-line mode. Spectra were acquired in positive ion mode from 250 to 1000 m/z at 70,000 resolution. Data were converted to imzML format66 (link) and analysed using MSiReader v1.067 (link). Lipid identity was performed by accurate mass using LIPID MAPS® structure database (<5 p.p.m.) (https://www.lipidmaps.org/data/structure/ ).
3
Isolation and Purification of Indole Alkaloids
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Harmine, harmane, and harmaline (purity > 98%) were isolated by HPLC from the seeds of P. harmala in our laboratory. Nor-harmane was purchased from Sigma Aldrich Co. (St. Louis, MO, United States). Scopolamine hydrobromide was purchased from TCI (Shanghai) Development, Co., Ltd. (Shanghai, China). The L-tryptophan (L-Trp), 5-hydroxytryptamine (5-HT), 5-hydroxyindole-3-acetic acid (5-HIAA), acetylcholine chloride (ACh), choline chloride (Ch), L-glutamic acid monosodium salt monohydrate (L-Glu), L-phenylalanine (L-Phe), L-tyrosine (L-Tyr), theophylline, tacrine (internal standard), and heparin sodium were purchased from Sigma Aldrich Co. (St. Louis, MO, United States). Perchloric acid and sodium hydroxide were purchased from Meilunbio® Biotech, Co., Ltd. (Dalian, China). Bovine serum albumin was purchased from YEASEN Biotechnology, Co., Ltd. (Shanghai, China). The HPLC-grade acetonitrile, methanol, and formic acid were purchased from Fisher Scientific, Co. (Santa Clara, CA, United States). Deionized water (>18 mΩ) was purified by Milli-Q Academic System (Millipore, Corp, Billerica, MA, United States).
4
HPLC-Grade Solvents for MSI
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All solvents for MSI (methanol, chloroform, ethanol, water) were HPLC grade or better, and were obtained from Biosolve bv. (Valkenswaard, The Netherlands). Norharmane was obtained from Sigma-Aldrich (Zwijndrecht, The Netherlands).
5
Lipid A Extraction and Mass Spectrometry
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Lipid A extraction was performed as per (45 (link)). Briefly, cells were solubilized in 4:3 70% isobutyric acid/1 M ammonium hydroxide (Sigma) and boiled at 100 °C for 30 min. Insoluble material was removed by centrifugation for 15 min at 2000 × g, following which supernatants were diluted 1:1 with ultrapure water and lyophilized. Extracts were washed with methanol twice before being reconstituted in 2:1:0.25 chloroform/methanol/water. Aliquots were spotted directly onto stainless steel targets 1:1 with the matrix norharmane (10 mg/ml [Sigma] in 2:1:0.25 chlorofom/methanol/water). Mass spectra were generated on a Bruker UltrafleXtreme (Bruker Daltonics, Billerica, MA) operated in reflectron mode across a mass range of 1000 to 2500 m/z, and a laser frequency of 2000 Hz using 40% global intensity.
6
Comprehensive Tissue Preparation Protocol
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2,5-Dihydroxybenzoic acid (DHB), norharmane, Fluoroshield with DAPI, Monoclonal Anti-Actin α-Smooth Muscle antibody, LC-MS grade methanol, HPLC grade chloroform, Bouin’s solution, Triton X-100, Tween 20, poly-L-lysine solution 0.1% and Peel-a-Way embedding molds (truncated, 12 × 12 × 20 mm) were purchased from Sigma-Aldrich, Saint Louis, MO, USA. Histology-grade solvents, Eosin G or Y (alcoholic solution 0.5%) and Masson’s Trichrome staining kit were purchased from DiaPath S.p.A., Martinengo, Italy, while QA-Agarose low melting point was obtained from MP Biomedical, Santa Ana, CA, USA. Harris hematoxylin, phosphate buffer saline (PBS) tablets, bovine serum albumin (BSA), SuperFrost Plus glass slides and cover slides were purchased from VWR International, LLC, Radnor, PA, USA. Trifluoroacetic acid (TFA), Antihuman CD68 antibody and AlexaFluor 568 goat anti mouse secondary antibody were purchased from Life Technologies-Invitrogen, Carlsbad, CA, USA. LC-MS grade water was purchased from Thermo Fisher Scientific, Rockford, IL, USA, while ITO coated glass slides for MALDI were obtained from Bruker Daltonics, Billerica, MA, USA. Paraformaldehyde 4% solution was purchased from Alfa Aesar, Haverhill, MA, USA.
7
Lipid Analysis Protocol Using Mass Spectrometry
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Norharmane and chloroform (≥99%) were
purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands) and used
without further purification. Methanol (ULC-MS grade), water (LC-MS
grade), ethanol (LC-MS grade), and xylene (AR grade) were purchased
from Biosolve (Valkenswaard, The Netherlands). Hematoxylin and Entellan
were purchased from Merck (Darmstadt, Germany), and eosin Y was purchased
from J.T. Baker (Center Valley, USA). Indium tin oxide (ITO) coated
glass slides were purchased from Delta Technologies (Loveland, USA).
A lipid standard of PS 18:0/18:1n-9 was purchased
from Avanti Polar Lipids (Alabaster, USA).
purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands) and used
without further purification. Methanol (ULC-MS grade), water (LC-MS
grade), ethanol (LC-MS grade), and xylene (AR grade) were purchased
from Biosolve (Valkenswaard, The Netherlands). Hematoxylin and Entellan
were purchased from Merck (Darmstadt, Germany), and eosin Y was purchased
from J.T. Baker (Center Valley, USA). Indium tin oxide (ITO) coated
glass slides were purchased from Delta Technologies (Loveland, USA).
A lipid standard of PS 18:0/18:1n-9 was purchased
from Avanti Polar Lipids (Alabaster, USA).
8
Synthesis and Characterization of Heterocyclic Compounds
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Harmane (CAS No. 486–84–0), norHarmane (CAS No. 244–63–3), 1,2,3,4-tetrahydroisoquinoline (TIQ; CAS No. 91–21–4), clorgyline hydrochloride (CAS No. 17780–75–5), and pargyline hydrochloride (CAS No. 306–07–0) were purchased from Sigma-Aldrich® (St. Louis, MO, United States of America). 2,3,6-trimethyl-1,4-naphtoquinone (TMN; CAS No. 20490–42–0) was purchased from Enamine Ltd. (Kyiv, Ukraine). Buspirone hydrochloride (CAS No. 33386–08–2) was purchased from Tocris Bioscience (Bio-Techne®, Minneapolis, MN, United States). The chemical structures of compounds are shown in Figure 1A .
9
Matrix Application for MALDI-MS Imaging
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Prior to matrix application,
the samples
were dried for 15 min. Norharmane (Sigma-Aldrich, Gillingham, UK)
matrix was applied to sections at 7 mg/mL in 2:1 chloroform:methanol
(v/v) using the TM-Sprayer M3 (HTX Technologies LLC, Carrboro, USA).
Eleven layers were applied with a drying time of 30 s between each
layer using a nozzle temperature of 30 °C with a flow rate of
120 μL/min. The velocity was set at 1200 mm/min combined with
a track passing of 3 mm allowing homogeneous matrix application.28 (link)
the samples
were dried for 15 min. Norharmane (Sigma-Aldrich, Gillingham, UK)
matrix was applied to sections at 7 mg/mL in 2:1 chloroform:methanol
(v/v) using the TM-Sprayer M3 (HTX Technologies LLC, Carrboro, USA).
Eleven layers were applied with a drying time of 30 s between each
layer using a nozzle temperature of 30 °C with a flow rate of
120 μL/min. The velocity was set at 1200 mm/min combined with
a track passing of 3 mm allowing homogeneous matrix application.28 (link)
10
Cryosectioning and MALDI-TOF MS Imaging
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A cryo-microtome (Leica CM 1860 UV, Leica Biosystems, Wetzlar, GE) was pre-equilibrated to −20 °C more than half an hour before cutting. Samples were sectioned at 10 µm thickness and thaw mounted on pre-cooled Indium Tin Oxide coated (ITO) slides. Slides were dried in desiccator for 15 min prior to matrix application.
Twelve layers of 7 mg/ml norharmane matrix solution (2: 1 chloroform/methanol (v: v)) were applied to the tissue sections using a HTX TM-sprayer (HTX Technologies, Chapel Hill, NC) at a 30 °C nozzle temperature and 0.120 mL/min flow rate. norharmane and chloroform were obtained from Sigma Aldrich (Zwijndrecht, the Netherlands). Methanol was obtained from Biosolve BV (Valkenswaard, the Netherlands).
Twelve layers of 7 mg/ml norharmane matrix solution (2: 1 chloroform/methanol (v: v)) were applied to the tissue sections using a HTX TM-sprayer (HTX Technologies, Chapel Hill, NC) at a 30 °C nozzle temperature and 0.120 mL/min flow rate. norharmane and chloroform were obtained from Sigma Aldrich (Zwijndrecht, the Netherlands). Methanol was obtained from Biosolve BV (Valkenswaard, the Netherlands).
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