Issue 11, 2004
From the journal:

Organic & Biomolecular Chemistry

Natural product based inhibitors of the thioredoxin–thioredoxin reductase system†

Peter Wipf,*a   Stephen M. Lynch,a   Anne Birmingham,b   Giselle Tamayo,cd   Allan Jiménez,c   Nefertiti Camposc  and  Garth Powisb  

* Corresponding authors

a Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
E-mail: pwipf@pitt.edu
Fax: +1-412-624-0787
Tel: +1-412-624-8606

b Arizona Cancer Center, University of Arizona, 1515 North Campbell Avenue, Tucson, AZ 85724, USA

c Instituto Nacional de Biodiversidad (INBio), Apdo. Postal 22-3100, Santo Domingo de Heredia, Costa Rica, América Central

d Escuela de Química, Universidad de Costa Rica, 2060 San José, Costa Rica, América Central

Abstract

Spiroketal naphthodecalins are readily assembled by Barton's base mediated Ullmann binaphthyl ether coupling, Dakin reactions and hypervalent iodine spirocyclization. The core structures can be further diversified by enone addition and Stille coupling reactions. Nanomolar inhibitors for the Trx/TrxR redox control system were prepared by this approach and compared to series of natural product isolates. Cytotoxicity in MCF-7 cell assays ranged from an IC50 of 1.6 to >100 µM.

Graphical abstract: Natural product based inhibitors of the thioredoxin–thioredoxin reductase system

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B402431A
Article type
Paper
Submitted
18 Feb 2004
Accepted
25 Mar 2004
First published
11 May 2004

Org. Biomol. Chem., 2004,2, 1651-1658

Permissions

Request permissions

Natural product based inhibitors of the thioredoxin–thioredoxin reductase system

P. Wipf, S. M. Lynch, A. Birmingham, G. Tamayo, A. Jiménez, N. Campos and G. Powis, Org. Biomol. Chem., 2004, 2, 1651 DOI: 10.1039/B402431A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements