Issue 13, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity†

Shaojun Zheng,ab   Luca Laraia,bc   Cornelius J. O' Connor,b   David Sorrell,c   Yaw Sing Tan,b   Zhaochao Xu,b   Ashok R. Venkitaraman,c   Wenjun Wu*a  and  David R. Spring*b  

* Corresponding authors

a Institute of Pesticide Science, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi 712100, China
E-mail: wuwenjun_1@163.com
Fax: +86 2987093987

b Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: spring@ch.cam.ac.uk
Fax: +44 1223 336362

c University of Cambridge, Medical Research Council Cancer Cell Unit, Hutchison/MRC Research Unit, Hills Road, Cambridge, UK

Abstract

A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cells. From this we have shown that all properties can be modulated independently by varying ring size and by moving the ester out of conjugation with the biaryl ring system. Increasing ring size increased redox activity and cytotoxicity, leading to the identification of a compound (10) which was significantly more cytotoxic. In addition compounds identified with a redox active scaffold and low cytotoxicity may be employed as a new class of redox probes.

Graphical abstract: Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

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Article information

DOI
https://doi.org/10.1039/C2OB25065A
Article type
Paper
Submitted
10 Jan 2012
Accepted
30 Jan 2012
First published
30 Jan 2012

Org. Biomol. Chem., 2012,10, 2590-2593

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Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

S. Zheng, L. Laraia, C. J. O' Connor, D. Sorrell, Y. S. Tan, Z. Xu, A. R. Venkitaraman, W. Wu and D. R. Spring, Org. Biomol. Chem., 2012, 10, 2590 DOI: 10.1039/C2OB25065A

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