Dinitrophenol

Manufactured by Merck Group

Sourced in United States

Dinitrophenol is a chemical compound that is used as a laboratory reagent. It functions as an uncoupler of oxidative phosphorylation, which is a process that generates adenosine triphosphate (ATP) in cells. Dinitrophenol can disrupt this process, leading to increased heat production and decreased ATP synthesis.

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2,4-dinitrophenol (26 citations) 2,4-dinitrophenol (DNP, (11 citations) 2,4-dinitrophenol (2,4-DNP), (4 citations) 2,4-dinitrophenol (D198501) (3 citations) Anti-2,4-dinitrophenol antibody (3 citations) Anti-dinitrophenol (DNP) IgE (3 citations) Monoclonal dinitrophenol (DNP)-specific IgE (2 citations) Anti-dinitrophenol (2 citations)

9 protocols using dinitrophenol

Mitochondrial Respiration Profiling

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Cells were plated to Seahorse XF96 cell culture microplates at 20,000 cells/well. Stock compounds in DMSO were diluted in RPMI (Gibco, Cat#11875119) medium to a final concentration in 100 mL volume, incubated at 37°C for 24 h, centrifuged at 200 × g for 2 min, and conditioned medium removed and replaced with serum-free RPMI (200 mL). Oxygen consumption rate (OCR) and extracellular acidification rate (ECAR) were measured after injections of 1 mg/mL oligomycin (Sigma, Cat# O4876), 50 mM dinitrophenol (Sigma, Cat# D198501), 1 mM rotenone (Sigma, Cat# R8875), and 10 mM antimycin A (Sigma, Cat# A8674). Analysis was performed by normalizing OCR and ECAR readouts to vehicle controls. Complex I and II activity were analyzed after permeabilization of the cells.

AbuEid M., Keyes R.F., McAllister D., Peterson F., Kadamberi I.P., Sprague D.J., Chaluvally-Raghavan P., Smith B.C, & Dwinell M.B. (2022). Fluorinated triphenylphosphonium analogs improve cell selectivity and in vivo detection of mito-metformin. iScience, 25(12), 105670.

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Metabolic Modulation in Cell Cultures

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2-deoxyglucose (2-DG) was purchased from Tocris Bioscience (Bristol, UK) and used at 20 mM. Dimethyl succinate was purchased from Sigma-Aldrich (St. Louis, MO) and used at 20 mM. Dinitrophenol was purchased from Sigma-Aldrich and used at 1 mM.

Alvero A.B., Montagna M.K., Sumi N.J., Joo W.D., Graham E, & Mor G. (2014). Multiple blocks in the engagement of oxidative phosphorylation in putative ovarian cancer stem cells: implication for maintenance therapy with glycolysis inhibitors. Oncotarget, 5(18), 8703-8715.

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Preparation of Biochemical Reagents

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Dinitrophenol, KCN, SHAM, 2,6-DHBA, and ASA were purchased from Sigma-Aldrich, St. Louis, MO. SA was purchased from Thermo Fisher Scientific Inc., Pittsburgh, PA. Salicylic acid, ASA, and 2,6-DHBA were dissolved in distilled water. Salicylhydroxamic acid was dissolved in 100% DMSO to produce 1 M stock solution.

, & Skubatz H. (2014). Thermoregulation in the appendix of the Sauromatum guttatum (Schott) inflorescence. Botanical Studies, 55, 68.

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Metabolic Stress Imaging of Myoblasts

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C₂C₁₂ cells (mouse myoblasts, ATCC CRL-1772) were grown in Gibco DMEM/F-12 (1:1) + GlutaMAX medium (ThermoFisher, 31331–028) supplemented by 10% FBS (Biowest, VWR #S1810–500). 24 hours before measurements, cells were seeded in #1.5 glass bottom microscopy wells (Nunc Lab-Tek II 8-well Chambered Coverglass), using the same medium. 30 minutes before measurements, the medium was changed to clear Gibco FluoroBrite DMEM imaging medium (ThermoFisher, A18967–01). The imaging medium contained either no additions (“control cells”), 200 µM dinitrophenol (Sigma D198501) (“DNP-exposed cells”) or 1 mM potassium cyanide (Sigma 60178) (“cyanide-exposed cells”).

Tornmalm J., Sandberg E., Rabasovic M, & Widengren J. (2019). Local redox conditions in cells imaged via non-fluorescent transient states of NAD(P)H. Scientific Reports, 9, 15070.

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Synthesis and Characterization of Mitochondrial Compounds

Cited 2 times

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2-Deoxyglucose, potassium superoxide, dtpa, ferricytochrome c, Tempol, oligomycin, dinitrophenol, and antimycin A were purchased from Sigma-Aldrich (St. Louis, MO, USA). DIPPMPO spin trap was synthesized, as reported previously [15 ,16 (link)]. Mito-CP was synthesized according to the previously published procedure [17 (link)]. Mito-Tempol₂ was from Cayman, and Mito-Tempol₄ was synthesized according to a modified procedure [18 (link)]. The synthetic pathway for Mito-CP-Ac is shown in Supplemental Figure 1.

Cheng G., Zielonka J., McAllister D., Hardy M., Ouari O., Joseph J., Dwinell M.B, & Kalyanaraman B. (2015). Antiproliferative effects of mitochondria-targeted cationic antioxidants and analogs: Role of mitochondrial bioenergetics and energy-sensing mechanism. Cancer letters, 365(1), 96-106.

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Pharmacological Modulators in Biological Assays

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Ketamine hydrochloride was purchased from Vedco, Inc. (St. Joseph, MO, USA). ALCAR, oligomycin A (oligomycin) and TMB-8 (3,4,5-trimethoxybenzoic acid 8-(diethylamino)octyl ester) were purchased from Sigma (St. Louis, MO, USA). Verapamil hydrochloride was purchased from TOCRIS Biosciences (Ellisville, MO, USA). All other reagents including dinitrophenol used in this study were purchased from Sigma unless mentioned otherwise. Verapamil (0.05 M) and ALCAR stock (1 M) solutions were made fresh with buffered egg water. Stocks of oligomycin A (10 mM), TMB-8 (0.5 M) and dinitrophenol (1 M) were prepared using dimethyl sulfoxide as the solvent.

Guo X., Dumas M., Robinson B.L., Ali S.F., Paule M.G., Gu Q, & Kanungo J. (2016). Acetyl L-carnitine targets adenosine triphosphate synthase in protecting zebrafish embryos from toxicities induced by verapamil and ketamine: An in vivo assessment. Journal of applied toxicology : JAT, 37(2), 192-200.

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Microfluidic Imaging of Mitochondrial Potential

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The microfluidic flow cell was first primed for 3 h with medium that included 3 μM DiOC₂(3) (Life Technologies). Cells were incubated in the flow cell in media containing 0.3 μM DiOC₂(3) for 30 min prior to imaging. We also included 0.3 μM DiOC₂(3) in the medium to which the cells were exposed during imaging. The period of depolarization was calculated as the interval between the first time point before depolarization began and the hyper-polarization peak.
When applying dinitrophenol (Sigma-Aldrich, St. Louis, MO, USA), 500 μg/mL was added to the media.

Rojas E.R., Huang K.C, & Theriot J.A. (2017). Homeostatic cell growth is accomplished mechanically through membrane tension-inhibition of cell wall synthesis. Cell systems, 5(6), 578-590.e6.

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Curcumin Supplementation in Diabetic Rats

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Curcumin (≥77%, 28260, Fluka-Sigma Aldrich, St. Louis, MO, USA) and analytical standard Curcumin (≥98.0%, 08511, Fluka-Sigma Aldrich, St. Louis, MO, USA), streptozotocin (STZ, Sigma Aldrich, St. Louis, MO, USA), dinitrophenol, and dimethyl sulfoxide (DMSO) were obtained from Sigma Aldrich (St. Louis, MO, USA); ketamine and xylazine were obtained from Agener União (Embu-Guaçu, SP, Brazil); acetonitrile and methanol (HPLC grade) were obtained from J. T. Baker (Mexico City, Mexico); acetic acid was obtained from Qhemis (Indaiatuba, SP, Brazil); and insulin (Biohulin NU-100; 100 units/mL) was obtained from Biobras (Montes Claros, MG, Brazil). Sodium hydroxide was purchased from Cetus (Santo Amaro, SP, Brazil) and plain yoghurt from Nestlé (Araras, SP, Brazil). Water was purified by a Millipore system (EMD Millipore, Darmstadt, Germany).

Gutierres V.O., Campos M.L., Arcaro C.A., Assis R.P., Baldan-Cimatti H.M., Peccinini R.G., Paula-Gomes S., Kettelhut I.C., Baviera A.M, & Brunetti I.L. (2015). Curcumin Pharmacokinetic and Pharmacodynamic Evidences in Streptozotocin-Diabetic Rats Support the Antidiabetic Activity to Be via Metabolite(s). Evidence-based Complementary and Alternative Medicine : eCAM, 2015, 678218.

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Cellular Antioxidant Response Assay

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Dulbecco’s Minimum Essential Medium (DMEM), Penicillin G, Streptomycin, Nystatin, Dimethyl sulfoxide (DMSO), Dichlorodihydrofluorescein diacetate (H₂DCFH-DA), Potassium chloride (KCl), Magnesium chloride (MgCl₂), Ethylene-di-amine-tetra acetate (EDTA), Protease inhibitor cocktail, HEPES, Hoechst-33258 (H258), propidium iodide (PI), RNAase, Di-nitrophenol and methylene blue were procured from Sigma chemicals Co. (St Louis, USA). Photosan (PS3) was procured from See Lab, Germany. Bicinchoninic acid (BCA, Thermo fisher scientific Rockford USA), primary and HRP conjugated secondary antibodies were procured from Santa Cruz, USA.

Bhatt A.N., Chauhan A., Khanna S., Rai Y., Singh S., Soni R., Kalra N, & Dwarakanath B.S. (2015). Transient elevation of glycolysis confers radio-resistance by facilitating DNA repair in cells. BMC Cancer, 15, 335.

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