Literature DB >> 24900226

From taxuspine x to structurally simplified taxanes with remarkable p-glycoprotein inhibitory activity.

Daniele Castagnolo1, Lorenzo Contemori1, Giorgio Maccari1, Stanislava I Avramova1, Annalisa Neri2, Gianpietro Sgaragli2, Maurizio Botta3.   

Abstract

Three simplified "non-natural" natural taxanes, related to taxuspine X, were synthetized and assayed as P-glycoprotein (P-gp) inhibitors. One of them (6) proved to be a very efficient P-gp inhibitor with an IC50 = 7.2 × 10(-6) M. In addition, to rationalize biological data, a pharmacophoric model was built through a ligand-based approach. This model represents the first example of a pharmacophore, which describes interactions of taxanes with P-gp.

Entities:  

Keywords:  MDR reversing agents; P-glycoprotein; Taxanes; macrolactone; non-natural natural product

Year:  2010        PMID： 24900226      PMCID： PMC4007961          DOI： 10.1021/ml100118k

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  25 in total

1.  Exploring multidrug resistance using rhodamine 123.

Authors:  D Kessel
Journal:  Cancer Commun       Date:  1989

2.  Synthesis and biological evaluation of new taxoids derived from 2-deacetoxytaxinine J.

Authors:  Maurizio Botta; Silvia Armaroli; Daniele Castagnolo; Gabriele Fontana; Paula Pera; Ezio Bombardelli
Journal:  Bioorg Med Chem Lett       Date:  2007-01-08       Impact factor: 2.823

3.  Synthesis of an original oxygenated taxuspine X analogue: a versatile "non-natural" natural product with remarkable P-gp modulating activity.

Authors:  Stanislava I Avramova; Elena Galletti; Michela L Renzulli; Gianluca Giorgi; Gianpietro Sgaragli; Daniela Alderighi; Chiara Ghiron; Federico Corelli; Marco Radi; Maurizio Botta
Journal:  ChemMedChem       Date:  2008-05       Impact factor: 3.466

4.  Design, synthesis and structure-activity relationships of novel taxane-based multidrug resistance reversal agents.

Authors:  Iwao Ojima; Christopher P Borella; Xinyuan Wu; Pierre-Yves Bounaud; Cecilia Fumero Oderda; Matthew Sturm; Michael L Miller; Subrata Chakravarty; Jin Chen; Qing Huang; Paula Pera; Tracy A Brooks; Maria R Baer; Ralph J Bernacki
Journal:  J Med Chem       Date:  2005-03-24       Impact factor: 7.446

Review 5.  The functions and structure of ABC transporters: implications for the design of new inhibitors of Pgp and MRP1 to control multidrug resistance (MDR).

Authors:  E Teodori; S Dei; C Martelli; S Scapecchi; F Gualtieri
Journal:  Curr Drug Targets       Date:  2006-07       Impact factor: 3.465

Review 6.  Pharmacological strategies for overcoming multidrug resistance.

Authors:  S Nobili; I Landini; B Giglioni; E Mini
Journal:  Curr Drug Targets       Date:  2006-07       Impact factor: 3.465

7.  Understanding tubulin-Taxol interactions: mutations that impart Taxol binding to yeast tubulin.

Authors:  Mohan L Gupta; Claudia J Bode; Gunda I Georg; Richard H Himes
Journal:  Proc Natl Acad Sci U S A       Date:  2003-05-09       Impact factor: 11.205

Review 8.  Targeting multidrug resistance in cancer.

Authors:  Gergely Szakács; Jill K Paterson; Joseph A Ludwig; Catherine Booth-Genthe; Michael M Gottesman
Journal:  Nat Rev Drug Discov       Date:  2006-03       Impact factor: 84.694

Review 9.  Taxol: a novel investigational antimicrotubule agent.

Authors:  E K Rowinsky; L A Cazenave; R C Donehower
Journal:  J Natl Cancer Inst       Date:  1990-08-01       Impact factor: 13.506

10.  Taxane-based reversal agents modulate drug resistance mediated by P-glycoprotein, multidrug resistance protein, and breast cancer resistance protein.

Authors:  Tracy A Brooks; Hans Minderman; Kieran L O'Loughlin; Paula Pera; Iwao Ojima; Maria R Baer; Ralph J Bernacki; Tracy Brooks
Journal:  Mol Cancer Ther       Date:  2003-11       Impact factor: 6.261
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  1 in total

1.  Synthesis of eunicellane-type bicycles embedding a 1,3-cyclohexadiene moiety.

Authors:  Alex Frichert; Peter G Jones; Thomas Lindel
Journal:  Beilstein J Org Chem       Date:  2018-09-20       Impact factor: 2.883
  1 in total

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