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      Thymoquinone (2-Isoprpyl-5-methyl-1, 4-benzoquinone) as a chemopreventive/anticancer agent: Chemistry and biological effects

      review-article
      Author(s): a , a , a , a , b , c , d , a , *
      Publication date (Electronic):
      Journal: Saudi Pharmaceutical Journal : SPJ
      Publisher: Elsevier
      Keywords: Thymoquinone, Phytopharmaceuticals, Natural compounds, Anti-cancer therapeutics, Plant products, TQ, thymoquinone, WHO, world health organization, THQ, thymohydroquinone, USD, United States Dollar, ROS, reactive oxygen species, RNS, reactive nitrogen species, PXRD, powder x-ray diffraction, FTIR, fourier-transform infrared spectroscopy, IUPAC, international union of pure and applied chemistry, NMR, nuclear magnetic resonance, SLNs, solid lipid nanoparticles, NLCs, nanostructured lipid carriers, NSAIDs, non-steroidal anti-inflammatory drugs, LPS, lipopolysaccharide, FGFs, fibroblast growth factors, TNFα, tumor necrosis factor alpha, VEGF, vascular endothelial growth factor, CDKs, cyclin-dependent kinases, TNBC, triple negative breast cancer, eEF-2K, elongation factor 2 kinase, EMT, epithelial to mesenchymal transition, TMZ, temozolomide, LKB1, liver kinase B1, AMPK, AMP-activated protein kinase, MC-A, myrtucommulone-A, RES, resveratrol, CDDP, cisplatin, SCLC, small cell lung carcinoma, OEC, oral epithelial cells, APC, adenomatous polyposis coli, XIAP, X-linked inhibitor of apoptosis protein, GBM, glioblastoma multiforme, HPDE, human pancreatic ductal epithelial cells, UMSCC, university of Michigan squamous cell carcinoma, PCNA, proliferating cell nuclear antigen

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          Abstract

          Cancer remains the topmost disorders of the mankind and number of cases is unceasingly growing at unprecedented rates. Although the synthetic anti-cancer compounds still hold the largest market in the modern treatment of cancer, natural agents have always been tried and tested for potential anti-cancer properties. Thymoquinone (TQ), a monoterpene and main ingredient in the essential oil of Nigella sativa L. has got very eminent rankings in the traditional systems of medicine for its anti-cancer pharmacological properties. In this review we summarized the diverse aspects of TQ including its chemistry, biosynthesis, sources and pharmacological properties with a major concern being attributed to its anti-cancer efficacies. The role of TQ in different aspects involved in the pathogenesis of cancer like inflammation, angiogenesis, apoptosis, cell cycle regulation, proliferation, invasion and migration have been described. The mechanism of action of TQ in different cancer types has been briefly accounted. Other safety and toxicological aspects and some combination therapies involving TQ have also been touched. A detailed literature search was carried out using various online search engines like google scholar and pubmed regarding the available research and review accounts on thymoquinone upto may 2019. All the articles reporting significant addition to the activities of thymoquinone were selected. Additional information was acquired from ethno botanical literature focusing on thymoquinone. The compound has been the centre of attention for a long time period and researched regularly in quite considerable numbers for its various physicochemical, medicinal, biological and pharmacological perspectives. Thymoquinone is studied for various chemical and pharmacological activities and demonstrated promising anti-cancer potential. The reviewed reports confirmed the strong anti-cancer efficacy of thymoquinone. Further in-vitro and in-vivo research is strongly warranted regarding the complete exploration of thymoquinone in ethnopharmacological context.

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          Lung cancer in never smokers: a review.

          Janakiraman Subramanian, Ramaswamy Govindan (2007)
          Lung cancer is the leading cause of cancer-related death in the United States. Although tobacco smoking accounts for the majority of lung cancer, approximately 10% of patients with lung cancer in the United States are lifelong never smokers. Lung cancer in the never smokers (LCINS) affects women disproportionately more often than men. Only limited data are available on the etiopathogenesis, molecular abnormalities, and prognosis of LCINS. Several etiologic factors have been proposed for the development of LCINS, including exposure to radon, cooking fumes, asbestos, heavy metals, and environmental tobacco smoke, human papillomavirus infection, and inherited genetic susceptibility. However, the relative significance of these individual factors among different ethnic populations in the development of LCINS has not been well-characterized. Adenocarcinoma is the predominant histologic subtype reported with LCINS. Striking differences in response rates and outcomes are seen when patients with advanced non-small-cell lung cancer (NSCLC) who are lifelong never smokers are treated with epidermal growth factor receptor tyrosine kinase (EGFR-TK) inhibitors such as gefitinib or erlotinib compared with the outcomes with these agents in patients with tobacco-associated lung cancer. Interestingly, the activating mutations in the EGFR-TK inhibitors have been reported significantly more frequently in LCINS than in patients with tobacco-related NSCLC. This review will summarize available data on the epidemiology, risk factors, molecular genetics, management options, and outcomes of LCINS.
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            Thymoquinone inhibits tumor angiogenesis and tumor growth through suppressing AKT and extracellular signal-regulated kinase signaling pathways.

            Gautam Sethi, Xiufeng Pang, Mingyao Liu … (2008)
            Thymoquinone, a component derived from the medial plant Nigella sativa, has been used for medical purposes for more than 2,000 years. Recent studies reported that thymoquinone exhibited inhibitory effects on cell proliferation of many cancer cell lines and hormone-refractory prostate cancer by suppressing androgen receptor and E2F-1. Whether thymoquinone inhibits tumor angiogenesis, the critical step of tumor growth and metastasis, is still unknown. In this study, we found that thymoquinone effectively inhibited human umbilical vein endothelial cell migration, invasion, and tube formation. Thymoquinone inhibited cell proliferation and suppressed the activation of AKT and extracellular signal-regulated kinase. Thymoquinone blocked angiogenesis in vitro and in vivo, prevented tumor angiogenesis in a xenograft human prostate cancer (PC3) model in mouse, and inhibited human prostate tumor growth at low dosage with almost no chemotoxic side effects. Furthermore, we observed that endothelial cells were more sensitive to thymoquinone-induced cell apoptosis, cell proliferation, and migration inhibition compared with PC3 cancer cells. Thymoquinone inhibited vascular endothelial growth factor-induced extracellular signal-regulated kinase activation but showed no inhibitory effects on vascular endothelial growth factor receptor 2 activation. Overall, our results indicate that thymoquinone inhibits tumor angiogenesis and tumor growth and could be used as a potential drug candidate for cancer therapy.
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              Thymoquinone and cisplatin as a therapeutic combination in lung cancer: In vitro and in vivo

              Syed H Jafri, Jonathan Glass, Runhua Shi … (2010)
              Background Thymoquinone (TQ) is a compound extracted from Black Caraway seeds of Nigella Sativa and is active against various cancers. Cisplatin (CDDP) is the most active chemotherapeutic agent in Lung Cancer. Here we report activity of TQ against non-small cell lung cancer (NSCLC) and small cell lung cancer (SCLC) cell lines alone and in combination with Cisplatin (CDDP). Methods For proliferation MTT assay, cell viability trypan blue assay and for apoptosis Annexin-V FITC assay were used in NCI-H460 and NCI-H146 cell lines. Inhibition of invasion by TQ was assessed using Matrigel assay and its affect on release of various cytokines was determined using RayBio Human Cytokine detection kit. Mouse xenograft model using NCI-H460 was used to determine in vivo activity of TQ and CDDP. Inhibition of LPS induced NF-κB expression by TQ was determined using transgenic mice expressing a luciferase reporter. Results TQ was able to inhibit cell proliferation, reduce cell viability and induce apoptosis. TQ at 100 μM and CDDP at 5 μM inhibited cell proliferation by nearly 90% and the combination showed synergism. TQ was able to induced apoptosis in both NCI-H460 and NCI-H146 cell lines. TQ also appears to affect the extracellular environment inhibiting invasion and reducing the production of two cytokines ENA-78 and Gro-alpha which are involved in neo-angiogenesis. Using a mouse xenograft model we were able to demonstrate that combination of TQ and CDDP was well tolerated and significantly reduced tumor volume and tumor weight without additional toxicity to the mice. In the combination arms (TQ5 mg/kg/Cis 2.5 mg/kg) tumor volume was reduced by 59% and (TQ20 mg/kg/Cis 2.5 mg/kg) by 79% as compared to control which is consistent with in vitro data. TQ down regulated NF-κB expression which may explain its various cellular activities and this activity may prove useful in overcoming CDDP resistance from over expression of NF-κB. Conclusions Thus TQ and CDDP appear to be an active therapeutic combination in lung cancer.
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                Author and article information

                Contributors
                Rehan Khan
                Journal
                Journal ID (nlm-ta): Saudi Pharm J
                Journal ID (iso-abbrev): Saudi Pharm J
                Title: Saudi Pharmaceutical Journal : SPJ
                Publisher: Elsevier
                ISSN (Print): 1319-0164
                ISSN (Electronic): 2213-7475
                Publication date PMC-release: 25 September 2019
                Publication date (Print): December 2019
                Publication date (Electronic): 25 September 2019
                Volume: 27
                Issue: 8
                Pages: 1113-1126
                Affiliations
                [a ]Department of Nano-Therapeutics, Institute of Nano Science and Technology, Habitat Centre, Phase 10, Sector 64, Mohali, Punjab 160062, India
                [b ]Department of Clinical Pharmacy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
                [c ]Department of Pharmacology and Toxicology, College of pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
                [d ]Translational Research Institute, Academic Health System, Hamad Medical Corporation, Doha, Qatar
                Author notes
                [* ]Corresponding author. rehankhan@ 123456inst.ac.in
                Article
                Publisher ID: S1319-0164(19)30122-7
                DOI: 10.1016/j.jsps.2019.09.008
                PMC ID: 6921197
                PubMed ID: 31885471
                SO-VID: 470cdabb-d814-464d-9d4c-387b4b22a8b2
                Copyright © © 2019 Production and hosting by Elsevier B.V. on behalf of King Saud University.
                License:

                This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                Date received : 12 July 2019
                Date accepted : 23 September 2019
                Categories
                Subject: Article

                Keywords: thymoquinone,phytopharmaceuticals,natural compounds,anti-cancer therapeutics,plant products,tq, thymoquinone,who, world health organization,thq, thymohydroquinone,usd, united states dollar,ros, reactive oxygen species,rns, reactive nitrogen species,pxrd, powder x-ray diffraction,ftir, fourier-transform infrared spectroscopy,iupac, international union of pure and applied chemistry,nmr, nuclear magnetic resonance,slns, solid lipid nanoparticles,nlcs, nanostructured lipid carriers,nsaids, non-steroidal anti-inflammatory drugs,lps, lipopolysaccharide,fgfs, fibroblast growth factors,tnfα, tumor necrosis factor alpha,vegf, vascular endothelial growth factor,cdks, cyclin-dependent kinases,tnbc, triple negative breast cancer,eef-2k, elongation factor 2 kinase,emt, epithelial to mesenchymal transition,tmz, temozolomide,lkb1, liver kinase b1,ampk, amp-activated protein kinase,mc-a, myrtucommulone-a,res, resveratrol,cddp, cisplatin,sclc, small cell lung carcinoma,oec, oral epithelial cells,apc, adenomatous polyposis coli,xiap, x-linked inhibitor of apoptosis protein,gbm, glioblastoma multiforme,hpde, human pancreatic ductal epithelial cells,umscc, university of michigan squamous cell carcinoma,pcna, proliferating cell nuclear antigen
                Data availability:
                Keywords: thymoquinone, phytopharmaceuticals, natural compounds, anti-cancer therapeutics, plant products, tq, thymoquinone, who, world health organization, thq, thymohydroquinone, usd, united states dollar, ros, reactive oxygen species, rns, reactive nitrogen species, pxrd, powder x-ray diffraction, ftir, fourier-transform infrared spectroscopy, iupac, international union of pure and applied chemistry, nmr, nuclear magnetic resonance, slns, solid lipid nanoparticles, nlcs, nanostructured lipid carriers, nsaids, non-steroidal anti-inflammatory drugs, lps, lipopolysaccharide, fgfs, fibroblast growth factors, tnfα, tumor necrosis factor alpha, vegf, vascular endothelial growth factor, cdks, cyclin-dependent kinases, tnbc, triple negative breast cancer, eef-2k, elongation factor 2 kinase, emt, epithelial to mesenchymal transition, tmz, temozolomide, lkb1, liver kinase b1, ampk, amp-activated protein kinase, mc-a, myrtucommulone-a, res, resveratrol, cddp, cisplatin, sclc, small cell lung carcinoma, oec, oral epithelial cells, apc, adenomatous polyposis coli, xiap, x-linked inhibitor of apoptosis protein, gbm, glioblastoma multiforme, hpde, human pancreatic ductal epithelial cells, umscc, university of michigan squamous cell carcinoma, pcna, proliferating cell nuclear antigen

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