Literature DB >> 8864242

(Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties.

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

Abstract

Reaction of the fungal sesquiterpene illudin S with excess paraformaldehyde in dilute H2SO4 gives (hydroxymethyl)acylfulvene. The primary allylic hydroxyl thus formed can undergo very facile replacement by a variety of nucleophiles. (Hydroxymethyl)acylfulvene (MGI.114) was more toxic than a precursor, acylfulvene, but less toxic than the parent compound illudin S to HL 60 cells.

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Year:  1996        PMID： 8864242     DOI： 10.1021/np960450y

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  17 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.  Acute retinal toxicity from the novel anti-tumor agent, Irofulven.

Authors:  Robert F Melendez; Joseph M Harrison; Eric K Rowinsky; Lisa A Hammond; Thomas D Fitzsimmons
Journal:  Doc Ophthalmol       Date:  2004-05       Impact factor: 2.379

3.  Drug discovery from natural sources.

Authors:  Young-Won Chin; Marcy J Balunas; Hee Byung Chai; A Douglas Kinghorn
Journal:  AAPS J       Date:  2006-04-14       Impact factor: 4.009

4.  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

5.  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

6.  Up-regulation of human prostaglandin reductase 1 improves the efficacy of hydroxymethylacylfulvene, an antitumor chemotherapeutic agent.

Authors:  Xiang Yu; Melanie M Erzinger; Kathryn E Pietsch; Frances N Cervoni-Curet; John Whang; John Niederhuber; Shana J Sturla
Journal:  J Pharmacol Exp Ther       Date:  2012-08-15       Impact factor: 4.030

7.  Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

Authors:  Dustin S Siegel; Grazia Piizzi; Giovanni Piersanti; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

8.  Irofulven, a novel inhibitor of DNA synthesis, in metastatic renal cell cancer.

Authors:  Robert J Amato; Cherie Perez; Lance Pagliaro
Journal:  Invest New Drugs       Date:  2002-11       Impact factor: 3.850

9.  Synergy of Irofulven in combination with various anti-metabolites, enzyme inhibitors, and miscellaneous agents in MV522 lung carcinoma cells: marked interaction with gemcitabine and 5-fluorouracil.

Authors:  Michael J Kelner; Trevor C McMorris; Rafael J Rojas; Leita A Estes; Pharnuk Suthipinijtham
Journal:  Invest New Drugs       Date:  2008-01-29       Impact factor: 3.850

Review 10.  Mushrooms: an emerging resource for therapeutic terpenoids.

Authors:  Adhiraj Dasgupta; Krishnendu Acharya
Journal:  3 Biotech       Date:  2019-09-24       Impact factor: 2.406
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