Sanguinarine induces apoptosis in A549 human lung cancer cells primarily via cellular glutathione depletion

Jang, Byeong‐Churl; Park, Jong-Gu; Song, Dae‐Kyu; Baek, Won-Ki; Yoo, Sun Kyun; Jung, Kyung‐Hwan; Park, Gy-Young; Lee, Tae-Yun; Suh, Seong-Il

doi:10.1016/j.tiv.2008.12.013

Cited by 79 publications

(65 citation statements)

References 46 publications

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“…In detail, it has been reported that micromolar concentrations of sanguinarine are capable of inhibiting tumor cell growth, and this inhibitory effect is associated with cell cycle arrest and induction of apoptosis [19][20][21][22] . The anti-proliferative and/ or pro-apoptotic activities of sanguinarine have been demonstrated in in vitro studies on several cancer cell types including epidermal [23] , keratinocyte [24,25] , prostate [26][27][28] , cervical [29] , breast [20,[30][31][32][33] , leukaemia [34,35] , lymphoma [36] , melanoma [37][38][39] , colon [40,41] , colorectal [21] , gastric [42] , pancreatic [19] , lung [22] , neuroendocrine [43] , osteosarcoma [44] , and human neuroblastoma cells [45] . By contrast, there are few studies on the in vivo effectiveness of sanguinarine administration per os [46,47] in animal tumor models [33,48] .…”

Section: Sanguinarine Induces Apoptosis In Tumor Cellsmentioning

confidence: 99%

“…Many reports indicate that sanguinarine exerts antitumor activity not only by inhibiting tumor cells migration and/ or invasion, but also by repressing angiogenesis [22,66] . Since solid tumors require active angiogenesis, the inhibition of endothelial cell proliferation result in the inhibition of tumor growth and progression.…”

Section: Inhibition Of Tumor Angiogenesis By Sanguinarinementioning

confidence: 99%

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Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives

Gaziano

Moroni

Buè

et al. 2016

WJGO

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Historically, natural products have represented a significant source of anticancer agents, with plant-derived drugs becoming increasingly explored. In particular, sanguinarine is a benzophenanthridine alkaloid obtained from the root of Sanguinaria canadensis , and from other poppy Fumaria species, with recognized anti-microbial, anti-oxidant and anti-inflammatory properties. Recently, increasing evidence that sanguinarine exibits anticancer potential through its capability of inducing apoptosis and/or antiproliferative effects on tumor cells, has been proved. Moreover, its antitumor seems to be due not only to its pro-apoptotic and inhibitory effects on tumor growth, but also to its antiangiogenic and anti-invasive properties. Although the precise mechanisms underlying the antitumor activity of this compound remain not fully understood, in this review we will focus on the most recent findings about the cellular and molecular pathways affected by sanguinarine, together with the rationale of its potential application in clinic. The complex of data currently available suggest the potential application of sanguinarine as an adjuvant in the therapy of cancer, but further pre-clinical studies are needed before such an antitumor strategy can be effectively translated in the clinical practice.

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Section: Sanguinarine Induces Apoptosis In Tumor Cellsmentioning

confidence: 99%

Section: Inhibition Of Tumor Angiogenesis By Sanguinarinementioning

confidence: 99%

Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives

Gaziano

Moroni

Buè

et al. 2016

WJGO

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“…1). In the past decades, these compounds have aroused interests of both chemists and pharmacologists for their chemical reactivity and extensive bioactivities including antitumor, [3][4][5] antimicrobial, [6][7][8][9][10][11][12] anti-inflammation, 13) antiplatelet aggregation, 14) anti-angiogenesis, 15) anti-acetylcholinesterase, 16) and antiparasite activities. [17][18][19][20] Our previous studies demonstrated that sanguinarine and chelerythrine ( Fig.…”

mentioning

confidence: 99%

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Yang

Yao

Qin

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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2-Aryl-3,4-dihydroisoquinolin-2-iums might be considered as a class of simple analogues of natural quaternary benzo[c]phenanthridine alkaloids. In this paper, 26 new 2-aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium bromides with various substituents in N-aromatic ring were synthesized from commercially available 1,3-benzodioxole in good to excellent yields. All the compounds were elucidated by MS, high resolution (HR)-MS, IR, 1 H-and 13 C-NMR analysis, and evaluated for antifungal activities in vitro against Alternaria alternate, Curvularia lunata and Fusarium oxysporum sp. niveum at 50 µg/mL. Most of the compounds showed higher activities against all the test fungi than their natural model compounds sanguinarine and chelerythrine. For A. alternate and Curvularia lunata, most of them were also more active than thiabendazole, a commercial fungicide standard. The structure-activity relationship indicated that the substituent in N-aromatic ring and its position had significant effect on the activity. The general trend was that halogen atoms and CF 3 remarkably enhanced the activity while CH 3 and OCH 3 decreased the activity. Generally, osubstituted isomers were more active than m-and p-substituted isomer. The present results suggest that the title compounds are potential for the development of new isoquinoline antimicrobial agents.Key words 3,4-dihydroisoquinolinium; 1,2,3,4-tetrahydroisoquinoline; N-heterocyclization; antifungal activity; CuCl 2 -catalyzed oxidative coupling reaction; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation Alkaloids represent a very extensive group of secondary metabolites with diverse structures, distribution in nature, and biological effects. Natural isoquinolines are one of the largest groups of alkaloids. Among them, there is a relatively small but important class of iminium moiety-containing isoquinoline alkaloids, such as quaternary benzo[c] phenanthridine alkaloids (QBAs), quaternary N-naphthyl isoquinolines, berberines and so on 1,2) (Fig. 1). In the past decades, these compounds have aroused interests of both chemists and pharmacologists for their chemical reactivity and extensive bioactivities including antitumor, [3][4][5] antimicrobial, [6][7][8][9][10][11][12] anti-inflammation, 13) antiplatelet aggregation, 14) anti-angiogenesis, 15) anti-acetylcholinesterase, 16) and antiparasite activities. [17][18][19][20] Our previous studies demonstrated that sanguinarine and chelerythrine ( Fig. 1) might serve as ideal lead compounds to develop new isoquinoline antimicrobial and acaricidal agents. Meanwhile, the iminium moiety (C= N + ) was their determinant for their bioactivities. 11,12,17) The similar cases were also found for antitumor activity of 7-demethyl chelerythrine (NK109) 21) and antibacterial activity of berberine.9) In addition, the molecular planarity was also proven to be an important factor for the activity.21) Based on understanding of the structure-activity relationship above and the aim of developing more potent QBAs-like drugs, we intended to design a cl...

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“…The antiproliferative and/or pro-apoptotic activities of sanguinarine have been demonstrated in cells derived from several human cancers including epidermal (Ahmad et al, 2000), keratinocytes (Adhami et al, 2003;Reagan-Shaw et al, 2006), prostate (Malikova et al, 2006b;Adhami et al, 2004;Huh et al, 2006), cervical (Ding et al, 2002), breast Debiton et al, 2003;Holy et al, 2006), leukemia (Han et al, 2008;Weerasinghe et al, 2001c;Weerasinghe et al, 2001b;Weerasinghe et al, 2001a), lymphoma (Hussain et al, 2007), melanoma (Burgeiro et al, 2013;Hammerova et al, 2011;Serafim et al, 2008), colon (Lee et al, 2012;Matkar et al, 2008), colorectal (Han et al, 2013a;Lee et al, 2012;Pica et al, 2012), gastric (Choi et al, 2009), pancreatic (Ahsan et al, 2007), lung (Jang et al, 2009), neuroendocrine (Larsson et al, 2010), osteosarcoma (Park et al, 2010), and in rat glioblastoma cells (Han et al, 2007), bladde (Han et al, 2013b). However, the impact of sanguinarine on neuroblastoma cells has not been shown.…”

Section: Discussionmentioning

confidence: 99%

“…Its principle medicinal use to date is in dental products based on its anti-bacterial, anti-fungal, and anti-inflammatory activities, which reduce both gingival inflammation and supragingival plaque formation (Godowski, 1989;Kuftinec et al, 1990;Laster and Lobene, 1990). Several recent studies have showed that sanguinarine, at micromolar concentration, inhibits the growth of cancer cells, and this inhibition of growth is associated with cell cycle arrest and the stimulation of apoptosis (Ahsan et al, 2007;Choi et al, 2008;Han et al, 2013a;Jang et al, 2009). The aim of this study is to determine in vitro effect of sanguinarine against neuroblastoma and to question which apoptotic genes contributes its apoptotic effect.…”

Section: Introductionmentioning

confidence: 98%

Promoting Effects of Sanguinarine on Apoptotic Gene Expression in Human Neuroblastoma Cells

Çeçen¹,

Altun²,

Erçetin³

et al. 2014

Asian Pacific Journal of Cancer Prevention

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Neuroblastoma is the most common extracranial solid tumor in children. Approximately half of the affected patients are diagnosed with high-risk poor prognosis disease, and novel therapies are needed. Sanguinarine is a benzophenanthridine alkaloid which has anti-microbial, anti-oxidant and anti-inflammatory properties. The aim of this study is whether sanguinarine has in vitro apoptotic effects and which apoptotic genes might be affected in the human neuroblastoma cell lines SH-SY5Y (N-myc negative), Kelly (N-myc positive, ALK positive), and SK-N-BE(2). Cell viability was analysed with WST-1 and apoptotic cell death rates were determined using TUNEL. After RNA isolation and cDNA conversion, expression of 84 custom array genes of apoptosis was determined. Sanguinarine caused cell death in a dose dependent manner in all neuroblastoma cell lines except SK-N-BE(2) with rates of 18% in SH-SY5Y and 21% in Kelly human neuroblastoma cells. Cisplatin caused similar apoptotic cell death rates of 16% in SH-SY5Y and 23% in Kelly cells and sanguinarine-cisplatin combinations caused the same rates (18% and 20%). Sanguinarine treatment did not affect apoptototic gene expression but decreased levels of anti-apoptotic genes NOL3 and BCL2L2 in SH-SY5Y cells. Caspase and TNF related gene expression was affected by the sanguinarine-cisplatin combination in SH-SY5Y cells. The expression of regulation of apoptotic genes were increased with sanguinarine treatment in Kelly cells. From these results, we conclude that sanguinarine is a candidate agent against neuroblastoma.

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Sanguinarine induces apoptosis in A549 human lung cancer cells primarily via cellular glutathione depletion

Cited by 79 publications

References 46 publications

Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives

Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Promoting Effects of Sanguinarine on Apoptotic Gene Expression in Human Neuroblastoma Cells

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