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Synthesis and biological evaluation of (-)-16-normethyldictyostatin: A potent analogue of (-)-dictyostatin

Shin, Y and Fournier, JH and Balachandran, R and Madiraju, C and Raccor, BS and Zhu, G and Edler, MC and Hamel, E and Day, BW and Curran, DP (2005) Synthesis and biological evaluation of (-)-16-normethyldictyostatin: A potent analogue of (-)-dictyostatin. Organic Letters, 7 (14). 2873 - 2876. ISSN 1523-7060

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Abstract

(Chemical Equation Presented) (-)-16-Normethyldictyostatin has been made by total synthesis and is a potent antitumor agent in cells expressing wild-type tubulin and in one mutant cell line that is resistant to paclitaxel, but it is much less active than dictyostatin in another paclitaxel-resistant cell line where Val is substituted for Phe270. This provides strong evidence that the C16 methyl group of the dictyostatins is oriented toward Phe270 in the paclitaxel-binding site on β-tubulin. © 2005 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Shin, Y
Fournier, JH
Balachandran, R
Madiraju, C
Raccor, BS
Zhu, G
Edler, MC
Hamel, E
Day, BW
Curran, DPcurran@pitt.eduCURRAN
Date: 7 July 2005
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 7
Number: 14
Page Range: 2873 - 2876
DOI or Unique Handle: 10.1021/ol050808u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Animals; Antineoplastic Agents--chemical synthesis; Antineoplastic Agents--chemistry; Antineoplastic Agents--pharmacology; Brain--anatomy & histology; Cattle; Drug Resistance, Neoplasm; Drug Screening Assays, Antitumor; Macrolides--chemical synthesis; Macrolides--chemistry; Macrolides--pharmacology; Molecular Structure; Paclitaxel--pharmacology; Phenylalanine--genetics; Stereoisomerism; Structure-Activity Relationship; Tubulin--biosynthesis; Valine--genetics
PubMed ID: 15987158
Date Deposited: 07 Aug 2013 14:41
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19517

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