Home LiteratureArticle Details
PMID: 18283613 Published · ppublish English Journal Article Review

Strategies for the synthesis of the novel antitumor agent peloruside A.

Current opinion in drug discovery & development ·Vol. 11 ·No. 2 ·2008-03-00 ·Pages 251-71

Williams DR, Nag PP, Zorn N

Abstract

The microtubule-stabilizing agent (+)-peloruside A has emerged as a potential therapeutic agent for the treatment of cancer. Two total syntheses have been published and these reports have stimulated additional studies to advance the methodology and strategies for accessing this molecular architecture. This review details the biological data, modeling and conformation analyses, and synthetic studies toward the synthesis of (+)-peloruside A, that were reported prior to December 2007.

MeSH Terms
Animals Antibiotics, Antineoplastic/chemical synthesis,chemistry,pharmacology Bridged Bicyclo Compounds, Heterocyclic/chemical synthesis,chemistry,pharmacology Humans Indicators and Reagents Lactones/chemical synthesis,chemistry,pharmacology Models, Molecular Neoplasms/drug therapy,pathology Structure-Activity Relationship
Chemicals
Antibiotics, Antineoplastic Bridged Bicyclo Compounds, Heterocyclic Indicators and Reagents Lactones peloruside A
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Williams David R
Indiana University, Department of Chemistry, 800 East Kirkwood Avenue, Bloomington, IN 47450, USA. williamd@indiana.edu
Nag Partha P
Zorn Nicolas
References (33)
33 references, click to expand
  1. Shared actions of endotoxin and taxol on TNF receptors and TNF release.
    Science. 1990 Apr 20;248(4953):370-2 PMID: 1970196
  2. Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.
    Angew Chem Int Ed Engl. 1998 Aug 17;37(15):1986-2012 PMID: 29711061
  3. Natural products as sources of new drugs over the last 25 years.
    J Nat Prod. 2007 Mar;70(3):461-77 PMID: 17309302
  4. Synthesis of the C(1)-C(12) segment of peloruside A by an alpha-benzyloxymethyl ketone aldol strategy.
    Org Lett. 2004 Mar 4;6(5):663-6 PMID: 14986944
  5. Total synthesis and absolute configuration of the novel microtubule-stabilizing agent peloruside A.
    Angew Chem Int Ed Engl. 2003 Apr 11;42(14):1648-52 PMID: 12698467
  6. The novel cytotoxic sponge metabolite peloruside A, structurally similar to bryostatin-1, has unique bioactivity independent of protein kinase C.
    Anticancer Drug Des. 2001 Apr-Jun;16(2-3):155-66 PMID: 11962513
  7. Total synthesis of (+)-peloruside A.
    Org Lett. 2005 Mar 31;7(7):1303-5 PMID: 15787492
  8. Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.
    Org Lett. 2001 Feb 22;3(4):573-5 PMID: 11178828
  9. Marine natural products as anticancer drugs.
    Mol Cancer Ther. 2005 Feb;4(2):333-42 PMID: 15713904
  10. Synthetic approaches to the microtubule stabilizing agent (-)-laulimalide.
    Curr Opin Drug Discov Devel. 2002 Nov;5(6):944-59 PMID: 12478725
  11. Peloruside A does not bind to the taxoid site on beta-tubulin and retains its activity in multidrug-resistant cell lines.
    Cancer Res. 2004 Aug 1;64(15):5063-7 PMID: 15289305
  12. Spatial and temporal variability of cytotoxic metabolites in populations of the New Zealand sponge Mycale hentscheli.
    J Chem Ecol. 2005 May;31(5):1161-74 PMID: 16124239
  13. The immunopharmacology of paclitaxel (Taxol), docetaxel (Taxotere), and related agents.
    Int Immunopharmacol. 2003 Dec;3(13-14):1699-714 PMID: 14636822
  14. Synthetic studies of microtubule stabilizing agent peloruside A: an asymmetric synthesis of C10-C24 segment.
    Tetrahedron Lett. 2003 Oct 6;44(41):7659-7661 PMID: 30443085
  15. Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule- stabilizing activity.
    Cancer Res. 2002 Jun 15;62(12):3356-60 PMID: 12067973
  16. The design, computer modeling, solution structure, and biological evaluation of synthetic analogs of bryostatin 1.
    Proc Natl Acad Sci U S A. 1998 Jun 9;95(12):6624-9 PMID: 9618462
  17. Synthesis of the C12-C19 fragment of (+)-peloruside A through a diastereomer-discriminating RCM reaction.
    Org Lett. 2005 May 26;7(11):2225-8 PMID: 15901175
  18. Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.
    J Org Chem. 2000 Jan 28;65(2):445-9 PMID: 10813954
  19. Peloruside A synergizes with other microtubule stabilizing agents in cultured cancer cell lines.
    Mol Pharm. 2007 Mar-Apr;4(2):269-80 PMID: 17397239
  20. Toward the total synthesis of natural peloruside a: stereoselective synthesis of the backbone of the core.
    Org Lett. 2004 Jan 8;6(1):71-4 PMID: 14703353
  21. Toward the synthesis of peloruside a: fragment synthesis and coupling studies.
    Org Lett. 2003 Feb 20;5(4):599-602 PMID: 12583779
  22. An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A.
    Tetrahedron Lett. 2003 May 12;44(20):3967-3969 PMID: 30393410
  23. Peloruside A, an antimitotic agent, specifically decreases tumor necrosis factor-alpha production by lipopolysaccharide-stimulated murine macrophages.
    Exp Biol Med (Maywood). 2007 May;232(5):607-13 PMID: 17463156
  24. Computational comparison of microtubule-stabilising agents laulimalide and peloruside with taxol and colchicine.
    Bioorg Med Chem Lett. 2004 Oct 4;14(19):4825-9 PMID: 15341932
  25. Toward a total synthesis of peloruside A: enantioselective preparation of the C8-C19 region.
    Org Lett. 2003 Dec 25;5(26):4959-61 PMID: 14682739
  26. The chemistry and biology of the bryostatin antitumour macrolides.
    Nat Prod Rep. 2002 Aug;19(4):413-53 PMID: 12195811
  27. Anticancer drugs from nature--natural products as a unique source of new microtubule-stabilizing agents.
    Nat Prod Rep. 2007 Apr;24(2):327-57 PMID: 17390000
  28. NMR determination of the bioactive conformation of peloruside A bound to microtubules.
    J Am Chem Soc. 2006 Jul 12;128(27):8757-65 PMID: 16819869
  29. Peloruside A enhances apoptosis in H-ras-transformed cells and is cytotoxic to proliferating T cells.
    Apoptosis. 2004 Nov;9(6):785-96 PMID: 15505421
  30. Stereoselective synthesis of the C(1)-C(11) fragment of peloruside A.
    Org Lett. 2005 Sep 1;7(18):3941-4 PMID: 16119937
  31. The intriguing biology of the tumour necrosis factor/tumour necrosis factor receptor superfamily: players, rules and the games.
    Immunology. 2005 May;115(1):1-20 PMID: 15819693
  32. Synergistic effects of peloruside A and laulimalide with taxoid site drugs, but not with each other, on tubulin assembly.
    Mol Pharmacol. 2006 Nov;70(5):1555-64 PMID: 16887932
  33. Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions.
    J Am Chem Soc. 2001 Jun 6;123(22):5260-7 PMID: 11457388
Article Info
Journal
Current opinion in drug discovery & development
Abbr.
Curr Opin Drug Discov Devel
ISSN
1367-6733
Published
2008-03-00
Pages
251-71
Language
English
Region
England
NLM ID
100887519
PMCID
PMC2693484
Subset
IM
Grants
NIGMS NIH HHS · R01 GM041560-23A2 · United States
NIGMS NIH HHS · R01 GM041560-24 · United States
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: product@genelibs.com