Literature DB >> 20024345

Total synthesis of a library of designed hybrids of the microtubule-stabilising anticancer agents taxol, discodermolide and dictyostatin.

Ian Paterson1, Guy J Naylor, Takeshi Fujita, Esther Guzmán, Amy E Wright.   

Abstract

A hybrid library of the marine natural products dictyostatin and discodermolide, incorporating the taxol or taxotere side chains, were synthesised; preliminary biological evaluation in the PANC-1 cancer cell line revealed significant antiproliferative activity, demonstrating that a macrolide scaffold is an effective surrogate for the baccatin core of taxol.

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Year:  2009        PMID： 20024345     DOI： 10.1039/b921237j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 in total

Review 1.  The Lithistida: important sources of compounds useful in biomedical research.

Authors:  Amy E Wright
Journal:  Curr Opin Biotechnol       Date:  2010-12       Impact factor: 9.740

Review 2.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

3.  Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.

Authors:  Wei Zhu; María Jiménez; Won-Hyuk Jung; Daniel P Camarco; Raghavan Balachandran; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

4.  Total synthesis and biological evaluation of a series of macrocyclic hybrids and analogues of the antimitotic natural products dictyostatin, discodermolide, and taxol.

Authors:  Ian Paterson; Guy J Naylor; Nicola M Gardner; Esther Guzmán; Amy E Wright
Journal:  Chem Asian J       Date:  2010-10-28

5.  Design and synthesis of (+)-discodermolide-paclitaxel hybrids leading to enhanced biological activity.

Authors:  Amos B Smith; Keizo Sugasawa; Onur Atasoylu; Chia-Ping Huang Yang; Susan Band Horwitz
Journal:  J Med Chem       Date:  2011-08-26       Impact factor: 7.446

6.  A highly step-economical synthesis of dictyostatin.

Authors:  Stephen Ho; Cyril Bucher; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-10       Impact factor: 15.336

7.  Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents.

Authors:  María Jiménez; Wei Zhu; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  Beilstein J Org Chem       Date:  2011-10-05       Impact factor: 2.883

Review 8.  Natural products from the Lithistida: a review of the literature since 2000.

Authors:  Priscilla L Winder; Shirley A Pomponi; Amy E Wright
Journal:  Mar Drugs       Date:  2011-12-15       Impact factor: 6.085

9.  Structural Determinants of the Dictyostatin Chemotype for Tubulin Binding Affinity and Antitumor Activity Against Taxane- and Epothilone-Resistant Cancer Cells.

Authors:  Chiara Trigili; Isabel Barasoain; Pedro A Sánchez-Murcia; Katja Bargsten; Mariano Redondo-Horcajo; Aurora Nogales; Nicola M Gardner; Arndt Meyer; Guy J Naylor; Elena Gómez-Rubio; Federico Gago; Michel O Steinmetz; Ian Paterson; Andrea E Prota; J Fernando Díaz
Journal:  ACS Omega       Date:  2016-12-13

10.  Taccalonolide C-6 Analogues, Including Paclitaxel Hybrids, Demonstrate Improved Microtubule Polymerizing Activities.

Authors:  April L Risinger; Shayne D Hastings; Lin Du
Journal:  J Nat Prod       Date:  2021-06-10       Impact factor: 4.803
  10 in total

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