In vitro production of reactive oxygen species (ROS) by sampangine
Tóm tắt
Sampangine is an azaoxoaporphine alkaloid with interesting biological activities. Elucidating the mode of action of sampangine is a topic of continuous research. Recently reported cell-based data have indicated heme-dysfunction and subsequent reactive oxygen species production as being responsible for the biological activity of the natural product. By using an in vitro biochemical assay the ability of sampangine to produce reactive oxygen species was confirmed. The production of reactive oxygen species occurred upon mild chemical reduction of sampangine in absence of any cellular components. In an additional structure-activity-relationship study, utilizing synthesized analogs of sampangine, we identified the 1,4-iminoquinone scaffold as the key motif for the observed reactive oxygen species production. To assess the ability of sampangine to induce DNA damage, the direct binding of sampangine to calf thymus—DNA was measured using UV–Visible spectroscopy. No DNA binding was observed when sampangine was tested against calf thymus -DNA up to a ratio of 1:100. This observation rules out the direct involvement of sampangine in DNA binding and damage.
Tài liệu tham khảo
citation_journal_title=Eukaryot Cell; citation_title=Role of heme in the antifungal activity of the azaoxoaporphine alkaloid sampangine; citation_author=AK Agarwal, T Xu, MR Jacob, Q Feng, MC Lorenz, LA Walker, AM Clark; citation_volume=7; citation_publication_date=2008; citation_pages=387-400; citation_doi=10.1128/EC.00323-07; citation_id=CR1
citation_journal_title=Eur J Med Chem; citation_title=New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays; citation_author=JB Baell, GA Holloway; citation_volume=53; citation_publication_date=2010; citation_pages=2719-2740; citation_doi=10.1021/jm901137j; citation_id=CR2
citation_journal_title=Nature; citation_title=Chemical con artists foil drug discovery; citation_author=JB Baell, MA Walters; citation_volume=513; citation_publication_date=2014; citation_pages=481-483; citation_doi=10.1038/513481a; citation_id=CR3
citation_journal_title=Justus Liebigs Ann Chem; citation_title=Polycyclische aromatische alkaloide, I. Synthese von Cleistopholin und Sampangin; citation_author=F Bracher; citation_volume=1989; citation_publication_date=1989; citation_pages=87-88; citation_doi=10.1002/jlac.198919890117; citation_id=CR4
citation_journal_title=J Biol Chem; citation_title=Menadione-induced reactive oxygen species generation via redox cycling promotes apoptosis of murine pancreatic acinar cells; citation_author=DN Criddle, S Gillies, HK Baumgartner-Wilson, M Jaffar, EC Chinje, S Passmore, M Chvanov, S Barrow, OV Gerasimenko, AV Tepikin, R Sutton, OH Petersen; citation_volume=281; citation_publication_date=2006; citation_pages=40485-40492; citation_doi=10.1074/jbc.M607704200; citation_id=CR5
citation_journal_title=Am J Physiol Cell Physiol; citation_title=Doxorubicin acts via mitochondrial ROS to stimulate catabolism in C2C12 myotubes; citation_author=LAA Gilliam, JS Moylan, EW Patterson, JD Smith, AS Wilson, Z Rabbani, MB Reid; citation_volume=302; citation_publication_date=2012; citation_pages=C195-202; citation_doi=10.1152/ajpcell.00217.2011; citation_id=CR6
citation_journal_title=Eukaryot Cell; citation_title=Sampangine inhibits heme biosynthesis in both yeast and human; citation_author=Z Huang, K Chen, T Xu, J Zhang, Y Li, W Li, AK Agarwal, AM Clark, JD Phillips, X Pan; citation_volume=10; citation_publication_date=2011; citation_pages=1536-1544; citation_doi=10.1128/EC.05170-11; citation_id=CR7
citation_journal_title=Dyes Pigm; citation_title=Binding of DNA with Rhodamine B: spectroscopic and molecular modelling studies; citation_author=M Islam, M Chakraborty, P Pandya, A Al Masum, N Gupta, S Mukhopadhyay; citation_volume=99; citation_publication_date=2013; citation_pages=412-422; citation_doi=10.1016/j.dyepig.2013.05.028; citation_id=CR8
citation_journal_title=Bioorg Med Chem Lett; citation_title=Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and cryptococcus neoformans; citation_author=Z Jiang, N Liu, G Dong, Y Jiang, Y Liu, X He, Y Huang, S He, W Chen, Z Li, J Yao, Z Miao, W Zhang, C Sheng; citation_volume=24; citation_publication_date=2014; citation_pages=4090-4094; citation_doi=10.1016/j.bmcl.2014.07.064; citation_id=CR9
citation_journal_title=Chem Commun; citation_title=The discovery of novel antifungal scaffolds by structural simplification of the natural product sampangine; citation_author=Z Jiang, N Liu, D Hu, G Dong, Z Miao, J Yao, H He, Y Jiang, W Zhang, Y Wang, C Sheng; citation_volume=51; citation_publication_date=2015; citation_pages=14648-14651; citation_doi=10.1039/C5CC05699C; citation_id=CR10
citation_journal_title=Assay Drug Dev Technol; citation_title=Development of a 384-well colorimetric assay to quantify hydrogen peroxide generated by the redox cycling of compounds in the presence of reducing agents; citation_author=PA Johnston, KM Soares, SN Shinde, CA Foster, TY Shun, HK Takyi, P Wipf, JS Lazo; citation_volume=6; citation_publication_date=2008; citation_pages=505-518; citation_doi=10.1089/adt.2008.151; citation_id=CR11
citation_journal_title=Tetrahedron; citation_title=Synthesis of eupomatidines 1,2 and 3 and related compounds including iminoquinolinequinone structure; citation_author=Y Kitahara, H Onikura, Y Shibano, S Watanabe, Y Mikami, A Kuboa; citation_volume=53; citation_publication_date=1997; citation_pages=6001-6010; citation_doi=10.1016/S0040-4020(97)00293-7; citation_id=CR12
citation_journal_title=Eur J Pharmacol; citation_title=Induction of apoptosis by the plant alkaloid sampangine in human HL-60 leukemia cells is mediated by reactive oxygen species; citation_author=J Kluza, R Mazinghien, K Degardin, A Lansiaux, C Bailly; citation_volume=525; citation_publication_date=2005; citation_pages=32-40; citation_doi=10.1016/j.ejphar.2005.09.050; citation_id=CR13
citation_journal_title=Molecules; citation_title=Azaphenanthrene alkaloids with antitumoral activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae); citation_author=ASSC Lúcio, JRGS Almeida, JM Barbosa-Filho, JCLR Pita, MVSC Branco, MFFM Diniz, MF Agra, EVL Da-Cunha, MS Silva, JF Tavares; citation_volume=16; citation_publication_date=2011; citation_pages=7125-7131; citation_doi=10.3390/molecules16087125; citation_id=CR14
citation_journal_title=J Nat Prod; citation_title=Sampangine (a copyrine alkaloid) exerts biological activities through cellular redox cycling of its quinone and semiquinone intermediates; citation_author=F Mahdi, JB Morgan, W Liu, AK Agarwal, MB Jekabsons, Y Liu, YD Zhou, DG Nagle; citation_volume=78; citation_publication_date=2015; citation_pages=3018-3023; citation_doi=10.1021/acs.jnatprod.5b00819; citation_id=CR15
citation_journal_title=Methods; citation_title=Integrating virtual and biochemical screening for protein tyrosine phosphatase inhibitor discovery; citation_author=KR Martin, P Narang, JL Medina-Franco, N Meurice, JP MacKeigan; citation_volume=65; citation_publication_date=2014; citation_pages=219-228; citation_doi=10.1016/j.ymeth.2013.08.013; citation_id=CR16
citation_journal_title=Chem Res Toxicol; citation_title=Mechanism of ascididemin-induced cytotoxicity; citation_author=SS Matsumoto, J Biggs, BR Copp, JA Holden, LR Barrows; citation_volume=16; citation_publication_date=2003; citation_pages=113-122; citation_doi=10.1021/tx025618w; citation_id=CR17
citation_journal_title=Arch Pharm; citation_title=Hetero analogues of the antimicrobial alkaloids cleistopholine and sampangine; citation_author=K Mink, F Bracher; citation_volume=340; citation_publication_date=2007; citation_pages=429-433; citation_doi=10.1002/ardp.200700064; citation_id=CR18
citation_journal_title=Tetrahedron Lett; citation_title=A divergent approach to the total synthesis of the marine pyridoacridine alkaloid eilatin and its synthetic isomer isoeilatin; citation_author=A Plodek, F Bracher; citation_volume=56; citation_publication_date=2015; citation_pages=1445-1447; citation_doi=10.1016/j.tetlet.2015.01.176; citation_id=CR19
citation_journal_title=Eur J Org Chem; citation_title=Synthesis of the azaoxoaporphine alkaloid sampangine and ascididemin-type pyridoacridines through TMPMgCl·LiCl-mediated ring closure; citation_author=A Plodek, M König, F Bracher; citation_volume=2015; citation_publication_date=2015; citation_pages=1302-1308; citation_doi=10.1002/ejoc.201403502; citation_id=CR20
citation_journal_title=J Med Chem; citation_title=Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines; citation_author=JR Peterson, JK Zjawiony, S Liu, CD Hufford, AM Clark, RD Rogers; citation_volume=35; citation_publication_date=1992; citation_pages=4069-4077; citation_doi=10.1021/jm00100a012; citation_id=CR21
citation_journal_title=Med Chem Commun; citation_title=Chemical motifs that redox cycle and their associated toxicity; citation_author=P Rana, R Naven, A Narayanan, Y Will, LH Jones; citation_volume=4; citation_publication_date=2013; citation_pages=1175; citation_doi=10.1039/c3md00149k; citation_id=CR22
citation_journal_title=J Nat Prod; citation_title=Sampangine, a new alkaloid from Cananga odorata; citation_author=JUM Rao, GS Gri, T Hanumaiah, KVJ Rao; citation_volume=49; citation_publication_date=1986; citation_pages=346-347; citation_doi=10.1021/np50044a029; citation_id=CR23
citation_journal_title=Assay Drug Dev Technol; citation_title=Profiling the NIH small molecule repository for compounds that generate H2O2 by redox cycling in reducing environments; citation_author=KM Soares, N Blackmon, TY Shun, SN Shinde, HK Takyi, P Wipf, JS Lazo, PA Johnston; citation_volume=8; citation_publication_date=2010; citation_pages=152-174; citation_doi=10.1089/adt.2009.0247; citation_id=CR24
citation_journal_title=Nat Rev Drug Discov; citation_title=Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach?; citation_author=D Trachootham, J Alexandre, P Huang; citation_volume=8; citation_publication_date=2009; citation_pages=579-591; citation_doi=10.1038/nrd2803; citation_id=CR25
citation_journal_title=Nature; citation_title=Oxidation state of the active-site cysteine in protein tyrosine phosphatase 1B; citation_author=RLM Montfort, M Congreve, D Tisi, R Carr, H Jhoti; citation_volume=423; citation_publication_date=2003; citation_pages=773-777; citation_doi=10.1038/nature01681; citation_id=CR26
citation_journal_title=RSC Adv; citation_title=Understanding cancer and the anticancer activities of naphthoquinones-a review; citation_author=KW Wellington; citation_volume=5; citation_publication_date=2015; citation_pages=20309-20338; citation_doi=10.1039/C4RA13547D; citation_id=CR27
citation_journal_title=J Biomol Screen; citation_title=A simple statistical parameter for use in evaluation and validation of high throughput screening assays; citation_author=JH Zhang, TDY Chung, KR Oldenburg; citation_volume=4; citation_publication_date=1999; citation_pages=67-73; citation_doi=10.1177/108705719900400206; citation_id=CR28