Wipf, P and Minion, DJ and Halter, RJ and Berggren, MI and Ho, CB and Chiang, GG and Kirkpatrick, L and Abraham, R and Powis, G
(2004)
Synthesis and biological evaluation of synthetic viridins derived from C(20)-heteroalkylation of the steroidal PI-3-kinase inhibitor wortmannin.
Organic and Biomolecular Chemistry, 2 (13).
1911 - 1920.
ISSN 1477-0520
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Abstract
A series of viridin analogs was prepared from wortmannin by nucleophilic ring opening at C(20) and evaluated against the signaling kinases PI-3-kinase and mTOR. Several subnanomolar enzyme inhibitors with orders of magnitude selectivity for PI-3-kinase and strong cytotoxic activity against four cancer cell lines were identified. Among the ten most promising derivatives, six demonstrated lower liver toxicity and greater promise for inhibition of tumor cell growth than the lead structure wortmannin.
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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) |
---|
Wipf, P | pwipf@pitt.edu | PWIPF | | Minion, DJ | | | | Halter, RJ | | | | Berggren, MI | | | | Ho, CB | | | | Chiang, GG | | | | Kirkpatrick, L | | | | Abraham, R | | | | Powis, G | | | |
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Date: |
7 July 2004 |
Date Type: |
Publication |
Journal or Publication Title: |
Organic and Biomolecular Chemistry |
Volume: |
2 |
Number: |
13 |
Page Range: |
1911 - 1920 |
DOI or Unique Handle: |
10.1039/b405431h |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
1477-0520 |
MeSH Headings: |
Alkylation; Androstadienes--chemistry; Androstadienes--pharmacology; Androstenes--chemical synthesis; Androstenes--chemistry; Androstenes--pharmacology; Androstenes--toxicity; Bacteriocins--chemical synthesis; Bacteriocins--chemistry; Bacteriocins--pharmacology; Bacteriocins--toxicity; Cell Line, Tumor; Cell Proliferation--drug effects; Humans; Inhibitory Concentration 50; Molecular Structure; Phosphatidylinositol 3-Kinases--antagonists & inhibitors; Phosphatidylinositols--chemistry; Phosphatidylinositols--metabolism; Protein Kinase Inhibitors--chemical synthesis; Protein Kinase Inhibitors--chemistry; Protein Kinase Inhibitors--pharmacology; Substrate Specificity |
PubMed ID: |
15227545 |
Date Deposited: |
30 Jan 2014 18:14 |
Last Modified: |
02 Feb 2019 15:57 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/20421 |
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