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Redox Report
Communications in Free Radical Research
Volume 5, 2000 - Issue 5
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Research Articles

Redox sensitive epidithiodioxopiperazines in biological mechanisms of toxicity

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Pages 257-264 | Published online: 19 Jul 2013

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TW Jordan. (2020) The cellular and molecular toxicity of sporidesmin. New Zealand Veterinary Journal 68:4, pages 203-213.
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D. P. Morgavi , H. Boudra, J. P. Jouany & the former B. Michalet-Doreau. (2004) Effect and stability of gliotoxin, an toxin, on rumen fermentation. Food Additives & Contaminants 21:9, pages 871-878.
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Articles from other publishers (47)

Xiaohua Li & Jianhua Ju. (2023) Intracellularly driven chemical modifications of antimicrobial secondary metabolites: Potent mechanisms of self-resistance. Pharmaceutical Science Advances, pages 100032.
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Lin-Fang Zhong, Juan Ling, Lian-Xiang Luo, Chang-Nian Yang, Xiao Liang & Shu-Hua Qi. (2023) Lecanicilliums A–F, Thiodiketopiperazine-Class Alkaloids from a Mangrove Sediment-Derived Fungus Lecanicillium kalimantanense. Marine Drugs 21:11, pages 575.
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Zhixian Ma, Ankun Zhou & Chengfeng Xia. (2022) Strategies for total synthesis of bispyrrolidinoindoline alkaloids. Natural Product Reports 39:5, pages 1015-1044.
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Wei Ye, Taomei Liu, Weiyang Zhang & Weimin Zhang. (2021) The Toxic Mechanism of Gliotoxins and Biosynthetic Strategies for Toxicity Prevention. International Journal of Molecular Sciences 22:24, pages 13510.
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Ji-Yeon Hwang, Beomkoo Chung, Oh-Seok Kwon, Sung Chul Park, Eunji Cho, Dong-Chan Oh, Jongheon Shin & Ki-Bong Oh. (2021) Inhibitory Effects of Epipolythiodioxopiperazine Fungal Metabolites on Isocitrate Lyase in the Glyoxylate Cycle of Candida albicans. Marine Drugs 19:6, pages 295.
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Rhys Brown, Emily Priest, Julian R. Naglik & Jonathan P. Richardson. (2021) Fungal Toxins and Host Immune Responses. Frontiers in Microbiology 12.
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Lovely Gupta, Shanu Hoda, Maansi Vermani & Pooja Vijayaraghavan. (2021) Understanding the fundamental role of virulence determinants to combat Aspergillus fumigatus infections: exploring beyond cell wall. Mycological Progress 20:4, pages 365-380.
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Magalie Boucher & T. William Jordan. (2021) Primary Impacts of the Fungal Toxin Sporidesmin on HepG2 Cells: Altered Cell Adhesion without Oxidative Stress or Cell Death. Toxins 13:3, pages 179.
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Meilin Zhu, Xuewen Zhang, Xuenan Huang, Haotian Wang, Komal Anjum, Qianqun Gu, Tianjiao Zhu, Guojian Zhang & Dehai Li. (2020) Irregularly Bridged Epipolythiodioxopiperazines and Related Analogues: Sources, Structures, and Biological Activities. Journal of Natural Products 83:6, pages 2045-2053.
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Ambre Dezaire, Christophe H. Marchand, Marine Vallet, Nathalie Ferrand, Soraya Chaouch, Elisabeth Mouray, Annette K. Larsen, Michèle Sabbah, Stéphane D. Lemaire, Soizic Prado & Alexandre E. Escargueil. (2020) Secondary Metabolites from the Culture of the Marine-derived Fungus Paradendryphiella salina PC 362H and Evaluation of the Anticancer Activity of Its Metabolite Hyalodendrin. Marine Drugs 18:4, pages 191.
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Chase R. Olsson, Joshua N. Payette, Jaime H. Cheah & Mohammad Movassaghi. (2020) Synthesis of Potent Cytotoxic Epidithiodiketopiperazines Designed for Derivatization. The Journal of Organic Chemistry 85:7, pages 4648-4662.
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Nelson G. M. Gomes, Renato B. Pereira, Paula B. Andrade & Patrícia Valentão. (2019) Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers. Marine Drugs 17:10, pages 551.
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Thomas N. Snaddon, Toya D. Scaggs, Colin M. Pearson & James W. B. Fyfe. (2019) A Modular Construction of Epidithiodiketopiperazines. Organic Letters 21:12, pages 4873-4877.
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Majid M. Heravi, Vahideh Zadsirjan, Pegah Saedi & Tayebeh Momeni. (2018) Applications of Friedel–Crafts reactions in total synthesis of natural products. RSC Advances 8:70, pages 40061-40163.
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Emma Reece, Sean Doyle, Peter Greally, Julie Renwick & Siobhán McClean. (2018) Aspergillus fumigatus Inhibits Pseudomonas aeruginosa in Co-culture: Implications of a Mutually Antagonistic Relationship on Virulence and Inflammation in the CF Airway. Frontiers in Microbiology 9.
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Timothy R. Hodges, Noah M. Benjamin & Stephen F. Martin. (2018) Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids. Tetrahedron 74:26, pages 3329-3338.
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Timothy R. Hodges, Noah M. Benjamin & Stephen F. Martin. (2017) Syntheses of Gliocladin C and Related Alkaloids. Organic Letters 19:9, pages 2254-2257.
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Sarah E. Wilkins, Martine I. Abboud, Rebecca L. Hancock & Christopher J. Schofield. (2016) Targeting Protein-Protein Interactions in the HIF System. ChemMedChem 11:8, pages 773-786.
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Blanka R. Szulc, Bruno C. Sil, Arnaud Ruiz & Stephen T. Hilton. (2015) A Common Precursor Approach to Structurally Diverse Natural Products: The Synthesis of the Core Structure of (?)-Clausenamide and the Total Synthesis of (?)-Hyalodendrin. European Journal of Organic Chemistry 2015:34, pages 7438-7442.
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Hannes F. Zipfel & Erick M. Carreira. (2015) A Unified Strategy to 6-5-6-5-6-Membered Epipolythiodiketopiperazines: Studies towards the Total Synthesis of Scabrosin Diacetate and Haematocin. Chemistry - A European Journal 21:35, pages 12475-12480.
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Stephen K. Dolan, Grainne O’Keeffe, Gary W. Jones & Sean Doyle. (2015) Resistance is not futile: gliotoxin biosynthesis, functionality and utility. Trends in Microbiology 23:7, pages 419-428.
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Raha S. Orfali, Amal H. Aly, Weaam Ebrahim, Mohamed S. Abdel-Aziz, Werner E.G. Müller, WenHan Lin, Georgios Daletos & Peter Proksch. (2015) Pretrichodermamide C and N-methylpretrichodermamide B, two new cytotoxic epidithiodiketopiperazines from hyper saline lake derived Penicillium sp.. Phytochemistry Letters 11, pages 168-172.
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Pranatchareeya Chankhamjon, Daniela Boettger‐Schmidt, Kirstin Scherlach, Barbara Urbansky, Gerald Lackner, Daniel Kalb, Hans‐Martin Dahse, Dirk Hoffmeister & Christian Hertweck. (2014) Biosynthesis of the Halogenated Mycotoxin Aspirochlorine in Koji Mold Involves a Cryptic Amino Acid Conversion. Angewandte Chemie International Edition 53:49, pages 13409-13413.
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Pranatchareeya Chankhamjon, Daniela Boettger‐Schmidt, Kirstin Scherlach, Barbara Urbansky, Gerald Lackner, Daniel Kalb, Hans‐Martin Dahse, Dirk Hoffmeister & Christian Hertweck. (2014) Biosynthesis of the Halogenated Mycotoxin Aspirochlorine in Koji Mold Involves a Cryptic Amino Acid Conversion. Angewandte Chemie 126:49, pages 13627-13631.
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Timothy R. Welch & Robert M. Williams. (2014) Epidithiodioxopiperazines. occurrence, synthesis and biogenesis. Nat. Prod. Rep. 31:10, pages 1376-1404.
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Fanny L. Cherblanc, Kathryn L. Chapman, Jim Reid, Aaron J. Borg, Sandeep Sundriyal, Laura Alcazar-Fuoli, Elaine Bignell, Marina Demetriades, Christopher J. Schofield, Peter A. DiMaggioJrJr, Robert Brown & Matthew J. Fuchter. (2013) On the Histone Lysine Methyltransferase Activity of Fungal Metabolite Chaetocin. Journal of Medicinal Chemistry 56:21, pages 8616-8625.
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Binbin Gu, Shan He, Xiaojun Yan & Lixin Zhang. (2013) Tentative biosynthetic pathways of some microbial diketopiperazines. Applied Microbiology and Biotechnology 97:19, pages 8439-8453.
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Nicolas Boyer, Karen C. Morrison, Justin Kim, Paul J. Hergenrother & Mohammad Movassaghi. (2013) Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids. Chemical Science 4:4, pages 1646.
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Fanny L. Cherblanc, Robert W. M. Davidson, Paolo Di Fruscia, Nitipol Srimongkolpithak & Matthew J. Fuchter. (2013) Perspectives on natural product epigenetic modulators in chemical biology and medicine. Natural Product Reports 30:5, pages 605.
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Chang Guo, Jin Song, Jian‐Zhou Huang, Peng‐Hao Chen, Shi‐Wei Luo & Liu‐Zhu Gong. (2011) Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine. Angewandte Chemie International Edition 51:4, pages 1046-1050.
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Chang Guo, Jin Song, Jian‐Zhou Huang, Peng‐Hao Chen, Shi‐Wei Luo & Liu‐Zhu Gong. (2011) Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine. Angewandte Chemie 124:4, pages 1070-1074.
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Nicolas Boyer & Mohammad Movassaghi. (2012) Concise total synthesis of (+)-gliocladins B and C. Chemical Science 3:6, pages 1798.
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Justin Kim & Mohammad Movassaghi. 2012. Total Synthesis of Natural Products. Total Synthesis of Natural Products 211 233 .
Stephen O. Duke & Franck E. Dayan. (2011) Modes of Action of Microbially-Produced Phytotoxins. Toxins 3:8, pages 1038-1064.
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Daniel H. Scharf, Nicole Remme, Andreas Habel, Pranatchareeya Chankhamjon, Kirstin Scherlach, Thorsten Heinekamp, Peter Hortschansky, Axel A. Brakhage & Christian Hertweck. (2011) A Dedicated Glutathione S -Transferase Mediates Carbon–Sulfur Bond Formation in Gliotoxin Biosynthesis . Journal of the American Chemical Society 133:32, pages 12322-12325.
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John E. DeLorbe, Salman Y. Jabri, Steven M. Mennen, Larry E. Overman & Fang-Li Zhang. (2011) Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors. Journal of the American Chemical Society 133:17, pages 6549-6552.
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Eriko Iwasa , Yoshitaka Hamashima  & Mikiko Sodeoka . (2011) Epipolythiodiketopiperazine Alkaloids: Total Syntheses and Biological Activities. Israel Journal of Chemistry 51:3-4, pages 420-433.
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Daniel H. Scharf, Nicole Remme, Thorsten Heinekamp, Peter Hortschansky, Axel A. Brakhage & Christian Hertweck. (2010) Transannular Disulfide Formation in Gliotoxin Biosynthesis and Its Role in Self-Resistance of the Human Pathogen Aspergillus fumigatus . Journal of the American Chemical Society 132:29, pages 10136-10141.
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Kristina M. Cook, Stephen T. Hilton, Jasmin Mecinović, William B. Motherwell, William D. Figg & Christopher J. Schofield. (2009) Epidithiodiketopiperazines Block the Interaction between Hypoxia-inducible Factor-1α (HIF-1α) and p300 by a Zinc Ejection Mechanism. Journal of Biological Chemistry 284:39, pages 26831-26838.
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Abil E. Aliev, Stephen T. Hilton, William B. Motherwell & David L. Selwood. (2006) A concise approach to the epidithiodiketopiperazine (ETP) core. Tetrahedron Letters 47:14, pages 2387-2390.
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Elizabeth J. Duncan, Mary P. Thompson & Sin H. Phua. (2005) Zinc protection of HepG2 cells from sporidesmin toxicity does not require de novo gene transcription. Toxicology Letters 159:2, pages 164-172.
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Donald M. Gardiner & Barbara J. Howlett. (2005) Bioinformatic and expression analysis of the putative gliotoxin biosynthetic gene cluster of Aspergillus fumigatus . FEMS Microbiology Letters 248:2, pages 241-248.
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S.T. Hilton, W.B. Motherwell, P. Potier, C. Pradet & D.L. Selwood. (2005) Observations on the reactivity of thiyl radicals derived from 3,6-epidithiodiketopiperazine-2,5-diones and related congeners. Bioorganic & Medicinal Chemistry Letters 15:9, pages 2239-2242.
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Christina L.L. Chai, John A. Elix, Paul B. Huleatt & Paul Waring. (2004) Scabrosin esters and derivatives: chemical derivatization studies and biological evaluation. Bioorganic & Medicinal Chemistry 12:22, pages 5991-5995.
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Donald M. Gardiner, Anton J. Cozijnsen, Leanne M. Wilson, M. Soledade C. Pedras & Barbara J. Howlett. (2004) The sirodesmin biosynthetic gene cluster of the plant pathogenic fungus Leptosphaeria maculans. Molecular Microbiology 53:5, pages 1307-1318.
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Paul H. Bernardo, Nicola Brasch, Christina L.L. Chai & Paul Waring. (2003) A Novel Redox Mechanism for the Glutathione-dependent Reversible Uptake of a Fungal Toxin in Cells. Journal of Biological Chemistry 278:47, pages 46549-46555.
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Christopher J. Moody, Alexandra M. Z. Slawin & David Willows. (2003) Dirhodium( ii ) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisom?nchnones), an approach to analogues of dehydrogliotoxin . Org. Biomol. Chem. 1:15, pages 2716-2722.
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