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Total and semisynthesis and in vitro studies of both enantiomers of 20-fluorocamptothecin

Tangirala, RS and Dixon, R and Yang, D and Ambrus, A and Antony, S and Agama, K and Pommier, Y and Curran, DP (2005) Total and semisynthesis and in vitro studies of both enantiomers of 20-fluorocamptothecin. Bioorganic and Medicinal Chemistry Letters, 15 (21). 4736 - 4740. ISSN 0960-894X

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Abstract

Both enantiomers of 20-fluorocamptothecin and the racemate have been prepared by total synthesis. The (R)-enantiomer is essentially inactive in a topoisomerase-I/DNA assay, while the (S)-enantiomer is much less active than (20S)-camptothecin. The lactone ring of 20-fluorocamptothecin hydrolyzes more rapidly than that of camptothecin in PBS. The results provide insight into the role of the 20-hydroxy group in the binding of camptothecin to topoisomerase-I and DNA. © 2005 Elsevier Ltd. All rights reserved.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Tangirala, RS
Dixon, R
Yang, D
Ambrus, A
Antony, S
Agama, K
Pommier, Y
Curran, DPcurran@pitt.eduCURRAN
Date: 1 November 2005
Date Type: Publication
Journal or Publication Title: Bioorganic and Medicinal Chemistry Letters
Volume: 15
Number: 21
Page Range: 4736 - 4740
DOI or Unique Handle: 10.1016/j.bmcl.2005.07.074
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0960-894X
MeSH Headings: Antineoplastic Agents--chemical synthesis; Antineoplastic Agents--pharmacology; Camptothecin--analogs & derivatives; Camptothecin--chemical synthesis; Camptothecin--chemistry; Camptothecin--pharmacology; Enzyme Inhibitors--chemical synthesis; Enzyme Inhibitors--pharmacology; Humans; Hydrogen Bonding; Hydrolysis; Kinetics; Stereoisomerism; Structure-Activity Relationship; Topoisomerase I Inhibitors
PubMed ID: 16140529
Date Deposited: 22 Jul 2013 17:35
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19372

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