O phenylendiamine

Manufactured by Merck Group

Sourced in United States

O-phenylendiamine is a chemical compound that is commonly used as a reagent in analytical and diagnostic laboratory applications. It serves as a precursor for the synthesis of various dyes and pharmaceuticals. O-phenylendiamine has a core function as a chemical building block for diverse laboratory and industrial purposes.

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10 protocols using o phenylendiamine

Synthesis of 5-(1H-benzimidazol-2-yl)-4-methyl-thieno[3,2-b]pyrrole

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Example 107

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0.050 g (0.30 mmol) of 4-methylthieno[3,2-b]pyrrole-5-carbaldehyde (Aldrich, Cat. N. CDS015804), 0.033 g (0.30 mmol) of o-phenylendiamine (Aldrich, Cat. N. P23938-5G) and iodobenzene diacetate (Aldrich, Cat. N. 178721-25G) were stirred at −15° C. in solvent free conditions. The mixture was then warmed to RT becoming a sticky brown oil. After stirring at RT for 1.5 h a further portion of 0.018 g (0.18 mmol) of o-phenylendiamine was added. The obtained dark oil was purified by column chromatography on silica gel (EtOAc/hexane 3:97, v:v to 30:70 v:v) to provide 0.025 g of 5-(1H-benzimidazol-2-yl)-4-methyl-thieno[3,2-b]pyrrole (33%). ¹H NMR (DMSO-d₆) δ (ppm): 12.74-12.57 (bs, 1H), 7.68-7.46 (m, 2H), 7.44-7.39 (m, 1H), 7.28-7.22 (m, 1H), 7.21-7.14 (m, 3H), 4.26 (s, 3H); MS (ESI): m/z: 254 [M+H]⁺.

US10961255B2. Imidazoles as histone demethylase inhibitors (2021-03-30). Istituto Europeo di Oncologia S.r.l. [IT]. Inventors: Paola Vianello [IT], Alessia Romussi [IT], Anna Cappa [IT], Paolo Trifiro′ [IT], Mario Varasi [IT], Luca Sartori [IT], Ciro Mercurio [IT].

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Synthesis of 5-(1H-benzimidazol-2-yl)-4-methyl-thieno[3,2-b]pyrrole

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Example 107

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US10562914B2. Imidazoles as histone demethylase inhibitors (2020-02-18). Istituto Europeo di Oncologia S.r.l. [IT]. Inventors: Paola Vianello [IT], Alessia Romussi [IT], Anna Cappa [IT], Paolo Trifiro' [IT], Mario Varasi [IT], Luca Sartori [IT], Ciro Mercurio [IT].

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Synthesis of Titanium-Based Schiff Base Complex

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All chemicals were purchased commercially and were used as received without further purification. The synthesis was carried out in three steps. In the first step, we prepared the Schiff base from o-vanillin (0.304 g, 2 mmol, o-vanillin 99%, Alfa Aesar) and o-phenylendiamine (0.108 g, 1 mmol, o-phenylenediamine 99%, Sigma–Aldrich) in 50 ml methanol [methanol (p.a.) was a product of CENTRALCHEM]. The Schiff base solution was stirred for 30 min. In the second step, titanium (IV) butoxide [0.340 g, 1 mmol (in a 5% surplus), titanium (IV) butoxide 97%, reagent grade, Sigma–Aldrich] was added to the Schiff base solution with vigorous stirring. The yellow Schiff base solution turned dark orange. The precipitated TiO₂ was filtered from the solution. Finally, we added H₂O₂ [0.034 g, 1 mmol (0.11 g, 30% solution), hydrogen peroxide 30%, reagent grade ISO, Sigma–Aldrich] and the dark orange solution turned light orange. The orange crystals dropped out of solution after 1 d in the refrigerator. After crystallization a single crystal suitable for X-ray was selected.

Kožíšková J.A., Breza M., Valko M., Herich P., Bučinský L, & Kožíšek J. (2021). Electronic structure of Schiff-base peroxo{2,2′-[1,2-phenylenebis(nitrilomethanylylidene)]bis(6-methoxyphenolato)}titanium(IV) monohydrate: a possible model structure of the reaction center for the theoretical study of hemoglobin. IUCrJ, 8(Pt 2), 295-304.

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Quantification of Antibody Isotypes

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Briefly, 96-well plates were coated overnight with purified goat anti-human IgA, IgG, or IgM antibodies (Jackson Immuno Research Laboratories, Pennsylvania, USA). After washing and blocking, plates were incubated for 1 h with the supernatants of the cultured cells. After washing, plates were incubated for 1 h with peroxidase-conjugated fragment of goat antihuman IgA, IgG or IgM antibodies (Jackson Immuno Research Laboratories), and the assay was developed with o-phenylendiamine (Sigma-Aldrich). Optical density was measured on a microtiter plate reader at 450 nm and Ig concentrations were calculated by interpolation with the standard curve.

Carsetti R., Di Sabatino A., Rosado M.M., Cascioli S., Piano Mortari E., Milito C., Grimsholm O., Aranburu A., Giorda E., Tinozzi F.P., Pulvirenti F., Donato G., Morini F., Bagolan P., Corazza G.R, & Quinti I. (2020). Lack of Gut Secretory Immunoglobulin A in Memory B-Cell Dysfunction-Associated Disorders: A Possible Gut-Spleen Axis. Frontiers in Immunology, 10, 2937.

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Quantification of Antibodies in Synovial Fluid

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Multiwell plates were coated with 100 μl per well of 10 μg/ml LPS in 0.15 M phosphate-buffered saline (PBS) pH 7.2 at 4 °C overnight. After incubation with 1:50 diluted SF, bound antibodies were demonstrated by reaction with goat anti-human IgA and peroxidase-conjugated rabbit anti-goat IgG (Sigma, St. Louis, MO, USA) followed by the addition of the enzyme substrate (H₂O₂) and chromogen O-phenylendiamine (Sigma). Optical density (OD) was measured at 490 nm in an ELISA reader (Bio-Rad, Hercules, CA, USA). Total IgA levels in SF were determined by radial immunodiffusion assay (Diffu-Plate kit, Biocientífica, Buenos Aires, Argentina)

Eliçabe R.J., Silva J.E., Dave M.N., Lacoste M.G., Tamashiro H., Blas R., Munarriz A., Rabinovich G.A, & Di Genaro M.S. (2017). Association between IL-17 and IgA in the joints of patients with inflammatory arthropathies. BMC Immunology, 18, 8.

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ELISA for Parasite-Specific Antibodies

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Parasite products (ES products or somatic homogenate MvH) were prepared as described by Vendelova et al. [4 (link), 9 (link)], and the protein content was assessed using Bradford protein assay reagent (BioRad, Hercules, CA, USA) and using BSA (Sigma-Aldrich, St. Louis, USA) as the standard.
To determine the specific IgG/IgM, flat-bottom 96-well plates (Nunc Maxisorp) were coated with worm antigens (2.5 μg/ml ES or MvH) in carbonate-bicarbonate coating buffer (pH 9.6) per night at 4 °C. The microplates were blocked for 1 h at room temperature with 10% bovine fetal serum-PBS solution. Sera/peritoneal exudates diluted 1:100 were incubated for 1 h at 37 °C. The microplates were then washed, and goat anti-mouse IgG/IgM peroxidase conjugates diluted 1:5000/1:2000 (Sigma-Aldrich, St. Louis, USA) were added for 1 h at 37 °C. After further washes, O-phenylendiamine (Sigma-Aldrich, St. Louis, MO, USA) was added as a substrate, and absorbance values were recorded at 492 nm. Results were expressed as the mean optical density (OD) ± SD. The cut-off levels were determined as the mean + 3.8 × SD of the antibody activity in the exudates of healthy mice after Lardeux et al. [10 (link)].

Mačak Kubašková T., Mudroňová D., Vargová M., Reiterová K, & Hrčková G. (2021). Cellular and humoral peritoneal immunity to Mesocestoides vogae metacestode infection in mice. Parasites & Vectors, 14, 54.

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Palladium-Catalyzed Iodobenzene Coupling

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Iodobenzene (I-Ph), sodium chloride (NaCl), palladium (II) acetate (Pd(CH₃CO₂)₂), methanol (MeOH), absolute ethanol (EtOH), N,N-Dimethylformamide (DMF), diethyl ether (Et₂O), dichloromethane (DCM), dodecane, and acetone were purchase from Merck^® (Kenilworth, NJ, USA) and used as received. Technical divinylbenzene (DVB, 90%), hydroxiethylcellulose (HEC), 3-allylsalicylaldehyde, o-phenylendiamine, methyl acrylate (MA), triethylamine (TEA) and, 2,2’-azobis(isobutyronitrile) (AIBN) were purchase from Sigma-Aldrich^® (Saint Louis, MO, USA). TEA was distilled at reduced pressure with CaH₂ and MA at normal pressure in presence of p-tert-butylcatechol as polymerization inhibitor. AIBN was purified by recrystallization from methanol.

Mella C., Torres C.C., Pecchi G, & Campos C.H. (2019). Mesoporous Palladium N,N’-Bis(3-Allylsalicylidene)o-Phenylenediamine-Methyl Acrylate Resins as Heterogeneous Catalysts for the Heck Coupling Reaction. Materials, 12(16), 2612.

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ELISA for Detecting Staphylococcal Enterotoxin J

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ELISA was performed in 96-well microplates (MICROLON 96 well microplate, Greiner Bio-One). Each well was coated with 100 µL of anti-SElJ∆C antibody (2 µg/mL) in 0.05 M carbonate-bicarbonate buffer (pH 9.6, Sigma-Aldrich Japan, Tokyo, Japan) at 4 °C overnight. Then, each well was blocked with 250 µL/well of PBS/0.1% BSA, and the plate was immediately emptied. Afterward, 100 µL/well of samples or standards were added and incubated at 37 °C for 2 h. After washing, 100 µL/well of horse radish peroxidase labeled anti-SElJ∆C antibody (2 µg/mL), which was diluted in Can Get Signal Immunoreaction Enhancer solution 1 (TOYOBO, Osaka, Japan), was added and incubated at 37 °C for 1 h. After wash each well, 100 µL/well of 0.8 mg/mL o-phenylendiamine (Sigma-Aldrich, St. Louis, MO, USA) in 0.05 M phosphate-citrate buffer (Sigma-Aldrich) was added and incubated for 20 min, 100 µL/well of 2 N H₂SO₄ was added. The absorbance at 490 nm was read with a microplate reader (Model 680, Bio-Rad Laboratories). Toxin concentrations were determined by converting absorbance to the corresponding concentrations by use of the standard curve.

Ono H.K., Hachiya N., Suzuki Y., Naito I., Hirose S., Asano K., Omoe K., Nakane A, & Hu D.L. (2018). Development of an Immunoassay for Detection of Staphylococcal Enterotoxin-Like J, A Non-Characterized Toxin. Toxins, 10(11), 458.

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Metallothionein-I Quantification Assay

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δ-aminolevulinic acid (δ-ALA), DL-dithiothreitol (DTT), rabbit metallothionein-I, o-phenylendiamine, thiobarbituric acid (TBA) and malonaldehyde bis- (dimethyl acetal) were obtained from Sigma (St. Louis, MO, USA); mouse anti-metallothionein-I/II, and peroxidase-conjugated to goat anti-mouse IgG were purchased from Dako Corporation (Carpinteria, CA, USA).

Braga M.M., Dick T., de Oliveira D.L., Scopel-Guerra A., Mussulini B.H., Souza D.O, & da Rocha J.B. (2015). Evaluation of zinc effect on cadmium action in lipid peroxidation and metallothionein levels in the brain. Toxicology Reports, 2, 858-863.

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Ligand-Induced Internalization of Chimeric hTAAR5

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To determine ligand-induced internalization and cell surface expression of the chimeric hTAAR5, a cell surface ELISA (enzyme-linked immunosorbent assay) was performed. Therefore, cells were transiently transfected with N-terminally HA-tagged receptors. For internalization studies, cells were additionally stimulated for six hours with 10 μM 3-T₁AM [22 (link)], 72 hours post-transfection. For samples at time point zero, incubation media were immediately replaced and cells fixed with 4% paraformaldehyde and blocked with 10% FBS overnight.
Cells were probed with a biotin labeled Anti-HA antibody (Roche, Basel, Switzerland) (1:200) and detected with horseradish peroxidase-labeled Streptavidin (BioLegend, London, UK) (1:2,500). Color reaction was achieved by adding the substrate o-phenylendiamine (Sigma Aldrich, St. Louis, MO) solved in a buffer composed of 0.1 M citric acid and 0.1 M sodium hydrogen-phosphate enriched with hydrogen peroxide. Reaction was stopped with sodium sulfite-oversaturated 1 M hydrogen chloride. Absorption was measured at 492 / 620 nm by using Anthos Reader 2001 (Anthos Labtech Instruments, Salzburg, Austria).

Dinter J., Mühlhaus J., Wienchol C.L., Yi C.X., Nürnberg D., Morin S., Grüters A., Köhrle J., Schöneberg T., Tschöp M., Krude H., Kleinau G, & Biebermann H. (2015). Inverse Agonistic Action of 3-Iodothyronamine at the Human Trace Amine-Associated Receptor 5. PLoS ONE, 10(2), e0117774.

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