Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide: Preparation and Biological Activity

Member of
HBOI Faculty Contributions
Contributors
Gunasekera, Sarath P.
Mickel, Stuart J.
Daeffler, Robert
Niederer, Daniel
Wright, Amy E.
Linley, P. A.
Pitts, Tara P.
Publisher
American Chemical Society and American Society of Pharmacognosy
Date Issued
2004
Note

A series of seven synthetic discodermolide analogues 2-8, which are minor side products generated during the final stages in the synthesis of (+)-discodermolide (1), have been purified and evaluated for in vitro cytotoxicity against A549, P388, MFC-7, NCI/ADR, PANC-1, and VERO cell lines. These synthetic analogues showed a significant variation of cytotoxicity and confirmed the importance of the C-7 hydroxy through C-17 hydroxy molecular fragment for potency. Specifically, these analogues suggested the relevance of the C-11 hydroxyl group, the C-13 double bond, and the C-16 (S) stereochemistry for the potency of (+)-discodermolide.

Language
English
Type
Text
Genre
article
Extent
9 p.
Subject (Topical)
Microtubules
Cancer --Research
Biopharmaceutics
Molecular biology
Stereochemistry
Identifier
3164107
Additional Information
A series of seven synthetic discodermolide analogues 2-8, which are minor side products generated during the final stages in the synthesis of (+)-discodermolide (1), have been purified and evaluated for in vitro cytotoxicity against A549, P388, MFC-7, NCI/ADR, PANC-1, and VERO cell lines. These synthetic analogues showed a significant variation of cytotoxicity and confirmed the importance of the C-7 hydroxy through C-17 hydroxy molecular fragment for potency. Specifically, these analogues suggested the relevance of the C-11 hydroxyl group, the C-13 double bond, and the C-16 (S) stereochemistry for the potency of (+)-discodermolide.
This document is the accepted manuscript version of a published work that appeared in final form in Journal of Natural Products after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/np030493w. This article may be cited as: Gunasekera, S. P., Mickel, S. J., Daeffler, R., Niederer, D., Wright, A. E., Linley, P. & Pitts, T. (2004). Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide: Preparation and Biological Activity. Journal of Natural Products, 67(5), 749-756.
Florida Atlantic University. Harbor Branch Oceanographic Institute contribution #1544.
Date Backup
2004
Date Text
2004
DOI
10.1021/np030493w
Date Issued (EDTF)
2004
Extension


FAU
FAU
admin_unit="FAU01", ingest_id="ing9355", creator="creator:BCHANG", creation_date="2011-04-25 13:56:10", modified_by="super:FAUDIG", modification_date="2014-02-10 14:23:07"

IID
FADT3164107
Issuance
single unit
Person Preferred Name

Gunasekera, Sarath P.

creator

Physical Description

pdf
9 p.
PURL
http://purl.flvc.org/FCLA/DT/3164107
Title Plain
Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide: Preparation and Biological Activity
URL
http://purl.flvc.org/FCLA/DT/3164107
Origin Information

American Chemical Society and American Society of Pharmacognosy
2004
single unit
Title
Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide: Preparation and Biological Activity
Other Title Info

Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide: Preparation and Biological Activity