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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Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Shin, Y | | | | Fournier, JH | | | | Balachandran, R | | | | Madiraju, C | | | | Raccor, BS | | | | Zhu, G | | | | Edler, MC | | | | Hamel, E | | | | Day, BW | | | | Curran, DP | curran@pitt.edu | CURRAN | |
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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-dev.library.pitt.edu/id/eprint/19517 |
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