Literature DB >> 8575564

Acylfulvenes, a new class of potent antitumor agents.

T C McMorris1, M J Kelner, W Wang, M A Diaz, L A Estes, R Taetle.   

Abstract

Acylfulvene, derived from the sesquiterpene illudin S by treatment with acid (reverse Prins reaction), is far less reactive to thiols than illudin S. However, it is reduced readily to an aromatic product, in the same way as illudin S. This may explain its greatly improved therapeutic index compared to that of the parent compound.

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Year:  1996        PMID： 8575564     DOI： 10.1007/bf01922420

Source DB:  PubMed          Journal:  Experientia        ISSN： 0014-4754


  11 in total

1.  Twenty-five cases of poisoning by the mushroom Pleurotus olearius.

Authors:  Z Maretić; F E Russell; V Golobić
Journal:  Toxicon       Date:  1975-11       Impact factor: 3.033

2.  FUNGAL METABOLITES. THE STRUCTURES OF THE NOVEL SESQUITERPENOIDS ILLUDIN-S AND -M.

Authors:  T C MCMORRIS; M ANCHEL
Journal:  J Am Chem Soc       Date:  1965-04-05       Impact factor: 15.419

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

Authors:  T C McMorris; M J Kelner; W Wang; S Moon; R Taetle
Journal:  Chem Res Toxicol       Date:  1990 Nov-Dec       Impact factor: 3.739

4.  Cloned low metastatic variants from human lung carcinoma metastases.

Authors:  N M Varki; A Tseng; T P Vu; L A Estes
Journal:  Anticancer Res       Date:  1990 May-Jun       Impact factor: 2.480

5.  Illudin S (lampterol).

Authors:  K Nakanishi; M Ohashi; M Tada; Y Yamada
Journal:  Tetrahedron       Date:  1965-05       Impact factor: 2.457

6.  Structure of lampterol (illudin S).

Authors:  T Matsumoto; H Shirahama; A Ichihara; Y Fukuoka; Y Takahashi; Y Mori; M Watanabe
Journal:  Tetrahedron       Date:  1965-09       Impact factor: 2.457

7.  Preclinical evaluation of illudins as anticancer agents.

Authors:  M J Kelner; T C McMorris; W T Beck; J M Zamora; R Taetle
Journal:  Cancer Res       Date:  1987-06-15       Impact factor: 12.701

8.  Metabolism by rat liver cytosol of illudin S, a toxic substance of Lampteromyces japonicus. II. Characterization of illudin S-metabolizing enzyme.

Authors:  K Tanaka; T Inoue; S Kadota; T Kikuchi
Journal:  Xenobiotica       Date:  1992-01       Impact factor: 1.908

Review 9.  Poisoning with the North American Jack O'Lantern mushroom, Omphalotus illudens.

Authors:  A L French; L K Garrettson
Journal:  J Toxicol Clin Toxicol       Date:  1988

10.  Efficacy of Acylfulvene Illudin analogues against a metastatic lung carcinoma MV522 xenograft nonresponsive to traditional anticancer agents: retention of activity against various mdr phenotypes and unusual cytotoxicity against ERCC2 and ERCC3 DNA helicase-deficient cells.

Authors:  M J Kelner; T C McMorris; L Estes; R J Starr; M Rutherford; M Montoya; K M Samson; R Taetle
Journal:  Cancer Res       Date:  1995-11-01       Impact factor: 12.701
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  11 in total

1.  Chemical and enzymatic reductive activation of acylfulvene to isomeric cytotoxic reactive intermediates.

Authors:  Kathryn E Pietsch; James F Neels; Xiang Yu; Jiachang Gong; Shana J Sturla
Journal:  Chem Res Toxicol       Date:  2011-10-14       Impact factor: 3.739

2.  Profiling patterns of glutathione reductase inhibition by the natural product illudin S and its acylfulvene analogues.

Authors:  Xiaodan Liu; Shana J Sturla
Journal:  Mol Biosyst       Date:  2009-07-08

3.  Susceptibility of the antioxidant selenoenyzmes thioredoxin reductase and glutathione peroxidase to alkylation-mediated inhibition by anticancer acylfulvenes.

Authors:  Xiaodan Liu; Kathryn E Pietsch; Shana J Sturla
Journal:  Chem Res Toxicol       Date:  2011-04-12       Impact factor: 3.739

4.  A phase II trial of 6-hydroxymethylacylfulvene (MGI-114, irofulven) in patients with advanced non-small cell cancer previously treated with chemotherapy.

Authors:  J E Dowell; D H Johnson; J S Rogers; Y Shyr; N McCullough; P Krozely; R F DeVore
Journal:  Invest New Drugs       Date:  2001       Impact factor: 3.850

5.  Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.

Authors:  Paul A Jackson; John C Widen; Daniel A Harki; Kay M Brummond
Journal:  J Med Chem       Date:  2016-12-20       Impact factor: 7.446

6.  Efficacy of HMAF (MGI-114) in the MV522 metastatic lung carcinoma xenograft model nonresponsive to traditional anticancer agents.

Authors:  M J Kelner; T C McMorris; L Estes; W Wang; K M Samson; R Taetle
Journal:  Invest New Drugs       Date:  1996       Impact factor: 3.850

7.  Improved efficacy of acylfulvene in colon cancer cells when combined with a nuclear excision repair inhibitor.

Authors:  Paul M van Midwoud; Shana J Sturla
Journal:  Chem Res Toxicol       Date:  2013-11-05       Impact factor: 3.739

8.  Quantification of acylfulvene- and illudin S-DNA adducts in cells with variable bioactivation capacities.

Authors:  Kathryn E Pietsch; Paul M van Midwoud; Peter W Villalta; Shana J Sturla
Journal:  Chem Res Toxicol       Date:  2012-12-19       Impact factor: 3.739

9.  Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines.

Authors:  Yi Li; Qing-Zhu Li; Li Huang; Hong Liang; Kai-Chuan Yang; Hai-Jun Leng; Yue Liu; Xu-Dong Shen; Xiao-Jun Gou; Jun-Long Li
Journal:  Molecules       Date:  2017-02-22       Impact factor: 4.411

10.  A Chemical Proteomic Analysis of Illudin-Interacting Proteins.

Authors:  Philipp Le; Matthew B Nodwell; Jürgen Eirich; Stephan A Sieber
Journal:  Chemistry       Date:  2019-09-03       Impact factor: 5.236
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