PMID: 2103329Nov 1, 1990Paper

On the mechanism of toxicity of illudins: the role of glutathione

Chemical Research in Toxicology
Trevor C McMorrisR Taetle

Abstract

Illudin M and illudin S, antitumor sesquiterpenes from Omphalotus illudens, have been found to react with thiols in a pH-dependent manner. The optimum pH values for reaction of illudin M with methyl thioglycolate, cysteine, and glutathione were 5.8, 5.6, and 6.1, respectively, and pseudo-first-order rate constants at 25 degrees C (10-fold excess of thiol) were 44 x 10(-3), 11.5 x 10(-3), and 11.3 x 10(-3) min-1. In all cases, thiol added to the alpha, beta-unsaturated ketone giving an unstable intermediate. Subsequent loss of the tertiary hydroxyl and opening of the cyclopropane ring afforded a stable aromatic product. The toxicity of illudin S to HL60 cells was increased by lowering glutathione levels in the cells and vice versa. General toxicity and antitumor activity of illudins are discussed in the light of these results.

Citations

Jan 16, 1996·Experientia·T C McMorrisR Taetle
Feb 24, 2005·Applied Microbiology and Biotechnology·Ben-Zion ZaidmanSolomon P Wasser
Jan 27, 1999·Biochemical Pharmacology·T C McMorrisM J Kelner
Nov 27, 2009·The Journal of Organic Chemistry·Dustin S SiegelMohammad Movassaghi
Jan 22, 2011·Chemical Research in Toxicology·Mostafa I FekryKent S Gates
Dec 12, 2012·Chemical Research in Toxicology·Kathryn E PietschShana J Sturla
Sep 11, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Christina L NordAnders Broberg
Mar 1, 1996·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·K TanakaT Kikuchi
Nov 18, 2015·Journal of Natural Products·Christina NordAnders Broberg
Jul 28, 1999·Biochemical Pharmacology·M C HerzigJ M Woynarowski
Mar 7, 2014·PloS One·Malgorzata Sztiller-SikorskaMalgorzata Czyz
Nov 6, 2007·Bioorganic & Medicinal Chemistry Letters·Trevor C McMorrisMichael J Kelner
Jun 16, 2010·Chemistry : a European Journal·Kiyosei TakasuYoshiji Takemoto
Jul 17, 2019·Chemistry : a European Journal·Philipp LeStephan A Sieber
Mar 5, 2020·Anatomia, histologia, embryologia·V A AneeshaDinesh Kumar
May 8, 2020·Chemical & Pharmaceutical Bulletin·Satoki AokiTetsuya Murayama
Feb 26, 2013·Chemical Communications : Chem Comm·Yuuki NagamotoKiyosei Takasu
May 23, 2013·Acta Crystallographica. Section F, Structural Biology and Crystallization Communications·Maureen B QuinClaudia Schmidt-Dannert
Feb 24, 2004·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Ryan A DickThomas W Kensler
Jan 19, 2021·Journal of General and Family Medicine·Takashi WatariYu Amano
Jul 30, 2020·Journal of Controlled Release : Official Journal of the Controlled Release Society·Nadia FattahiHélder A Santos
Jan 14, 2010·Journal of Medicinal Chemistry·Trevor C McMorrisMichael J Kelner
Apr 15, 2021·Bioscience, Biotechnology, and Biochemistry·Satoki AokiTetsuya Murayama
Sep 1, 1996·Journal of Natural Products·T C McMorrisR Taetle
Apr 10, 2012·Chemical Reviews·Marina Tanasova, Shana J Sturla
Jan 30, 2007·Journal of the American Chemical Society·Jiachang GongShana J Sturla
Sep 1, 2001·The Journal of Organic Chemistry·T C McMorrisM J Kelner
Dec 6, 2003·The Journal of Organic Chemistry·Trevor C McMorrisMichael J Kelner

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.