Thymoquinone

Manufactured by Merck Group

Sourced in United States, Germany, Italy, India, United Kingdom, Sao Tome and Principe

Thymoquinone is a chemical compound commonly used in laboratory settings. It is a naturally occurring quinone that is found in the seeds of the Nigella sativa plant. Thymoquinone is known for its potential biological activities, which may be of interest in various research applications. However, a detailed description of its core function is not available at this time while maintaining an unbiased and factual approach.

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Spelling variants of this product

Thymoquinone (TQ) (12 citations) Standard Thymoquinone (2 citations) Thymoquinone (2-isopropyl-5 methyl-1,4-benzoquinone) (2 citations)

99 protocols using thymoquinone

Extraction and Quantification of Egg Phospholipids and Thymoquinone

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Phospholipid (phosphatidylcholine) was extracted from chicken egg yolk in the laboratory. Egg phosphatidylcholine (PC, purity > 96.5%) was obtained from Lipoid (Germany) to be used as a reference standard in the UHPLC analysis of extracted egg phospholipid (EP). Acetonitrile and HPLC grade M ethanol were purchased from BDH Chemicals Ltd. (U.K.).
Black seed oil was bought from local market (Bangladesh). For quantification of amount of thymoquinone present in black seed oil, thymoquinone and Potassium dihydrogen phosphate were procured from Sigma-Aldrich (USA) and Winlab Ltd (UK) respectively. Cholesterol (Ch) was purchased from LobaChemie (India). M ethanol, ethanol, dicholoromethane, acetone, BHT (Butylatedhydroxytoluene), sodium dihydrogen phosphate, and poly-ethylene glycol 6000 (PEG600) were obtained from Merck (Germany). Sodium chloride (NaCl) was obtained from Sigma-Aldrich (USA). All other reagents were of analytical grade and used without further purification.

Rushmi Z.T., Akter N., Mow R.J., Afroz M., Kazi M., de Matas M., Rahman M, & Shariare M.H. (2016). The impact of formulation attributes and process parameters on black seed oil loaded liposomes and their performance in animal models of analgesia. Saudi Pharmaceutical Journal : SPJ, 25(3), 404-412.

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Thymoquinone preparation for cell studies

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Thymoquinone (274666-1G, Sigma-Aldrich, USA) was prepared by dissolving 0.4926% Thymoquinone crystal in 1% dimethyl sulfoxide anhydrous, ≥99.9% (276855, Sigma -Aldrich, USA) and 99.9% NK media (130-092-657, Miltenyi biotec, USA). Two dilutions of the extract, 25 and 50 μM, were prepared and stored at 2–8°C.

Alshaibi H.F., Aldarmahi N.A., Alkhattabi N.A., Alsufiani H.M, & Tarbiah N.I. (2022). Studying the Anticancer Effects of Thymoquinone on Breast Cancer Cells through Natural Killer Cell Activity. BioMed Research International, 2022, 9218640.

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Thymoquinone and Nigella sativa Oil Preparation

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Thymoquinone was obtained from commercial sources in high purity (> 98 %, Sigma-Aldrich) whereas Nigella sativa oil was obtained from local producer (> 10 % Thymoquinone, AweCemre, Tokat, Turkey). Both samples were dissolved individually in dimethyl sulfoxide (DMSO, Sigma) and diluted further with Dulbecco's modifi ed Eagle's medium (DMEM, Sigma) to obtain the required fi nal concentrations for the assays listed below in detail.

Kus G., Ozkurt M., Kabadere S., Erkasap N., Goger G, & Demirci F. (2018). Antiproliferative and antiapoptotic effect of thymoquinone on cancer cells in vitro. Bratislavske lekarske listy, 119(5).

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Methotrexate and Spirulina Antioxidant Study

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The Methotrexate injectable solution with a concentration of 50 mg/5 mL was obtained from Mina Pharm Pharmaceuticals located in Cairo, Egypt. Thymoquinone with 98% purity was supplied by Sigma Aldrich (Saint Louis, MO, USA). Spirulina platensis was obtained from the Algal Biotechnology unit at the National Research Center located in Dokki, Cairo, Egypt. Biodiagnostic CO, Cairo, Egypt provided kits for assessing the levels of MDA, SOD, GSH, and CAT. R&D, Mannheim, Germany provided AChE assay kits. ELISA kits to evaluate cytokines IL-1β, IL-6, and TNF-α (Mybiosource Company, USA) to measure inflammatory processes.

Behairy A., Elkomy A., Elsayed F., Gaballa M.M., Soliman A, & Aboubakr M. (2023). Antioxidant and anti-inflammatory potential of spirulina and thymoquinone mitigate the methotrexate-induced neurotoxicity. Naunyn-Schmiedeberg's Archives of Pharmacology, 397(3), 1875-1888.

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Thymoquinone-Chitosan Nanoparticles for Cell Culture

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Thymoquinone (Sigma Aldrich; WGK, Germany), medium molecular weight chitosan (190–310 kDa, 75–85% deacetylated) and polyvinyl alcohol (PVA) (Sigma Aldrich; Saint Lois, USA). Tween 80, Acetone and dichloromethane (Merck; Darmstadt, Germany). Poly lactic-co-glycolic acid 5004 (Purasorb; Corbion Purac, Holland). Coumarin-6 (Sigma-Aldrich; Milwaukee, Wisconsin, USA). High glucose of Dulbecco’s modified Eagle medium containing phenol red, L-glutamine and sodium pyruvate (Nacalai Tesque Inc; Kyoto, Japan), fetal bovine serum (Tico Europe; South America), HEPES buffer (Gibco, Life Technology Corporation; Auckland, New Zealand), the penicillin-streptomycin antibiotic (Gibco Invitrogen; Auckland, New Zealand), Tryple E (Gibco, Fischer Scientific; Massachusets, USA). Tissue culture wares (American Type Cell Culture (ATCC); Manassas, USA), all organic solvents used were of HPLC grade. MTT [3-(4,5-Dimethyl-thiazol-2-yl)-2, S-diphenyltetrazolium bromide] (Merck; Darmstadt, Germany), and dimethylsulfoxide (DMSO) (Sigma-Aldrich, Darmstadt, Germany).

Ibrahim W.N., Muizzuddin Bin Mohd Rosli L, & Doolaanea A.A. (2020). Formulation, Cellular Uptake and Cytotoxicity of Thymoquinone-Loaded PLGA Nanoparticles in Malignant Melanoma Cancer Cells. International Journal of Nanomedicine, 15, 8059-8074.

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Thymoquinone Gel Formulation and Evaluation

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99% pure extract of Thymoquinone (Extract from Sigma Aldrich Company – Product No. 274666) was obtained in crystal form which was converted to powdered form using a mortar and pestle. Then all the ingredients were accurately weighed and a total bulk of 500 gm of gel was prepared. Base of the gel was prepared by 14 gm of carbopol mixed with 485 ml of hot water heated at a temperature of 80–90° C and stirred for 30 min to facilitate hydration. 1 gm of Thymoquinone was added to the mixture to attain a 0.2% concentration of Thymoquinone in the gel prepared and was stirred until homogenization. The pH of the gel was adjusted to 7.0 with 1 N Sodium hydroxide. Then the mixture was cooled at the room temperature (35 °C) and 2 drops of the Strawberry flavour were added to the mixture.
The drug was analyzed at 253 nm on UV–visible spectrophotometer for drug release estimation. The results showed that drug release from 0.2% Thymoquinone gel after 8 h was 95.01 ± 1.26.

Kapil H., Suresh D.K., Bathla S.C, & Arora K.S. (2018). Assessment of clinical efficacy of locally delivered 0.2% Thymoquinone gel in the treatment of periodontitis. The Saudi Dental Journal, 30(4), 348-354.

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Ramipril-Thymoquinone Formulation Development

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Ramipril (RMP) was purchased from Jai Radhe Sales (Ahmedabad, India). Thymoquinone (THQ) was purchased from Sigma-Aldrich (St. Louis, MO, USA). Imwitor 988 (I988), Imwitor 308 (I308), Kolliphor EL (KrEL), high-purity Kolliphor EL (KrEL HP), and Kolliphor RH40 (Kr-RH40) were purchased from BASF (Ludwigshafen, Germany). Hydrogenated castor oil (grade HCO30) was supplied by Nicole chemical Co., (Tokyo, Japan). Super-refined Tween 80 (SR-T80) was obtained from CRODA (Dusseldorf, Germany). Tween 85 (T85) and Tween 20 (T20) were supplied by Merck-Schuchardt OHG (Germany) and BDH (England), respectively. The cosolvent Transcutol^® P (TCP) (purified diethylene glycol monoethyl ether) was supplied by Gattefossé (Lyon, France). HPMC capsules (size 2) and fish gelatin capsules (size 00) were donated by Capsugel (Greenwood, SC, USA). All other reagents were of analytical grade and used without further purification.

Shahba A.A., Sherif A.Y., Elzayat E.M, & Kazi M. (2022). Combined Ramipril and Black Seed Oil Dosage Forms Using Bioactive Self-Nanoemulsifying Drug Delivery Systems (BIO-SNEDDSs). Pharmaceuticals, 15(9), 1120.

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Thymoquinone Mitigates Spinal Cord Injury

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The rats were equally divided into 5 random groups: Group S: Sham + normal saline (NS), Group C: SCI + NS, Group T100: SCI + thymoquinone 100 mg/kg/PO, Group T200: SCI + thymoquinone 200 mg/kg/PO, and Group T400: SCI + thymoquinone 400 mg/kg/PO.
All groups were subjected to mechanical and heat–cold tests before the start of the experiment. With the exception of the sham group, SCI was applied to all of the animals. Two weeks later, the mechanical and heat–cold tests were repeated, and the sham and control groups were given a single dose of NS, whereas the other groups were given the appropriate dose of thymoquinone (Sigma catalog-274666; Cas No. 490-91-5, in sterile packaging) in NS by nasogastric feeding tube. Doses of thymoquinone were chosen according to the study by Abdel-Fattah et al.⁸ The mechanical and heat–cold hypersensitivity tests were repeated at 30, 60, 120, and 180 minutes after receiving NS or thymoquinone. After all animals were anesthetized (using 80 mg/kg ketamine), they were put to death after 180 minutes by removal of intracardiac blood and perfusion of NS with 10% formaldehyde.

Çelik F., Göçmez C., Karaman H., Kamaşak K., Kaplan İ., Akıl E., Tufek A., Guzel A, & Uzar E. (2014). Therapeutic Effects of Thymoquinone in a Model of Neuropathic Pain. Current Therapeutic Research, Clinical and Experimental, 76, 11-16.

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Formulation and Characterization of Thymoquinone Nanocarriers

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BASF (Badische Anilin- und Soda Fabrik, Ludwigshafen, Germany) with the support of BASF Italia and BTC Chemical Distribution Unit (Cesano Maderno, Monza, and Brianza, Italy) kindly provided Soluplus^® and Solutol^® HS15. Distilled water was obtained from a Simplicity^® UV Water Purification System, Merck Millipore (Merck KGaA, Darmstadt, Germany). Thymoquinone, Phosphate buffered saline BioPerformance Certified pH 7.4 (PBS), Tween^® 80, lecithin (≥99%, TLC) lyophilized powder, cholesterol BioReagent (≥99), Methanol HPLC grade, Acetonitrile HPLC grade, Dimethyl sulfoxide (DMSO) HPLC grade, Formic acid analytical grade, 1,7-octadiene (98%), Dichloromethane (CH2Cl2) were purchased from Sigma–Aldrich (Milan, Italy). Sigma–Aldrich Merck (Milan, Italy) also supplied Dulbecco’s modified Eagle’s medium (DMEM), Ham’s F-12 nutrient mixture, fetal bovine serum (FBS), L-glutamine, penicillin and streptomycin, 1-(4,5-dimethylthiazol-2-yl)-3,5-diphenyl formazan (MTT) and other chemicals. Disposable plastics were obtained from Sarstedt (Nümbrecht, Germany).

Bergonzi M.C., Vasarri M., Marroncini G., Barletta E, & Degl’Innocenti D. (2020). Thymoquinone-Loaded Soluplus®-Solutol® HS15 Mixed Micelles: Preparation, In Vitro Characterization, and Effect on the SH-SY5Y Cell Migration. Molecules, 25(20), 4707.

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Profiling natural compound library

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A library of 502 natural compounds was obtained from Enzo Biochem (Farmingdale, NY, USA). Thymoquinone, MG132, geldanamycin (GA), and cycloheximide (CHX) were purchased from Sigma Aldrich (St. Louis, MO, USA). Antibodies recognizing HIF-1α (#3716), Pro564-OH-HIF-1α (#3434), PHD1 (sc-293220), PHD2 (#4835), PHD3 (ab30782), HSP90 (sc-69703), and β-tubulin (sc-9104) were purchased from Cell Signaling Technology (Danvers, MA, USA), Santa Cruz Biotechnology (Dallas, TX, USA), and Abcam (Cambridge, MA, USA).

Lee Y.M., Kim G.H., Park E.J., Oh T.I., Lee S., Kan S.Y., Kang H., Kim B.M., Kim J.H, & Lim J.H. (2019). Thymoquinone Selectively Kills Hypoxic Renal Cancer Cells by Suppressing HIF-1α-Mediated Glycolysis. International Journal of Molecular Sciences, 20(5), 1092.

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