Literature DB >> 17184797

The shape of things to come: structural and synthetic studies of taxol and related compounds.

David G I Kingston1.   

Abstract

The history of the development of Taxol (paclitaxel) as an anticancer drug is reviewed, and some aspects of the phytochemistry of Taxus species and of the medicinal chemistry of taxol are discussed. The nature of the taxol-tubulin interaction is then described, with an emphasis on studies that led to the discovery and experimental proof of the T-taxol conformation as the tubulin-binding conformation of taxol. The implications of this conformation for future drug development are also briefly covered.

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Year:  2006        PMID: 17184797      PMCID: PMC1979092          DOI: 10.1016/j.phytochem.2006.11.009

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  35 in total

1.  The binding conformation of Taxol in beta-tubulin: a model based on electron crystallographic density.

Authors:  J P Snyder; J H Nettles; B Cornett; K H Downing; E Nogales
Journal:  Proc Natl Acad Sci U S A       Date:  2001-04-17       Impact factor: 11.205

2.  Phytochemistry and medicinal plants.

Authors:  J D Phillipson
Journal:  Phytochemistry       Date:  2001-02       Impact factor: 4.072

Review 3.  Natural products as sources of new drugs over the period 1981-2002.

Authors:  David J Newman; Gordon M Cragg; Kenneth M Snader
Journal:  J Nat Prod       Date:  2003-07       Impact factor: 4.050

4.  Conformation of microtubule-bound paclitaxel determined by fluorescence spectroscopy and REDOR NMR.

Authors:  Y Li; B Poliks; L Cegelski; M Poliks; Z Gryczynski; G Piszczek; P G Jagtap; D R Studelska; D G Kingston; J Schaefer; S Bane
Journal:  Biochemistry       Date:  2000-01-18       Impact factor: 3.162

5.  [Drugs from nature. The biology of taxane].

Authors:  Eckhard Leistner
Journal:  Pharm Unserer Zeit       Date:  2005

Review 6.  [New microtubule stabilizers].

Authors:  Knut Baumann
Journal:  Pharm Unserer Zeit       Date:  2005

Review 7.  Chemotherapy of breast cancer: are the taxanes going to change the natural history of breast cancer?

Authors:  J M Nabholtz; K Tonkin; M Smylie; H J Au; M A Lindsay; J Mackey
Journal:  Expert Opin Pharmacother       Date:  2000-01       Impact factor: 3.889

8.  Rotational-echo double-resonance NMR distance measurements for the tubulin-bound Paclitaxel conformation.

Authors:  Younkee Paik; Chao Yang; Belhu Metaferia; Shoubin Tang; Susan Bane; Rudravajhala Ravindra; Natasha Shanker; Ana A Alcaraz; Scott A Johnson; Jacob Schaefer; Robert D O'Connor; Lynette Cegelski; James P Snyder; David G I Kingston
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

9.  Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew.

Authors:  A Stierle; G Strobel; D Stierle
Journal:  Science       Date:  1993-04-09       Impact factor: 47.728

10.  Phase I trial of taxol given as a 24-hour infusion every 21 days: responses observed in metastatic melanoma.

Authors:  P H Wiernik; E L Schwartz; A Einzig; J J Strauman; R B Lipton; J P Dutcher
Journal:  J Clin Oncol       Date:  1987-08       Impact factor: 44.544

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  21 in total

1.  Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli.

Authors:  Parayil Kumaran Ajikumar; Wen-Hai Xiao; Keith E J Tyo; Yong Wang; Fritz Simeon; Effendi Leonard; Oliver Mucha; Too Heng Phon; Blaine Pfeifer; Gregory Stephanopoulos
Journal:  Science       Date:  2010-10-01       Impact factor: 47.728

Review 2.  Natural products as leads to anticancer drugs.

Authors:  M Gordaliza
Journal:  Clin Transl Oncol       Date:  2007-12       Impact factor: 3.405

3.  Bioactivity-guided mapping and navigation of chemical space.

Authors:  Steffen Renner; Willem A L van Otterlo; Marta Dominguez Seoane; Sabine Möcklinghoff; Bettina Hofmann; Stefan Wetzel; Ansgar Schuffenhauer; Peter Ertl; Tudor I Oprea; Dieter Steinhilber; Luc Brunsveld; Daniel Rauh; Herbert Waldmann
Journal:  Nat Chem Biol       Date:  2009-06-28       Impact factor: 15.040

4.  Late-stage chemoselective functional-group manipulation of bioactive natural products with super-electrophilic silylium ions.

Authors:  Trandon A Bender; Philippa R Payne; Michel R Gagné
Journal:  Nat Chem       Date:  2017-09-18       Impact factor: 24.427

5.  Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine.

Authors:  Peter M Njogu; Jiri Gut; Philip J Rosenthal; Kelly Chibale
Journal:  ACS Med Chem Lett       Date:  2013-05-22       Impact factor: 4.345

Review 6.  Engineering microbial factories for synthesis of value-added products.

Authors:  Jing Du; Zengyi Shao; Huimin Zhao
Journal:  J Ind Microbiol Biotechnol       Date:  2011-04-28       Impact factor: 3.346

7.  Accurate mass-time tag library for LC/MS-based metabolite profiling of medicinal plants.

Authors:  Daniel J Cuthbertson; Sean R Johnson; Jasenka Piljac-Žegarac; Julia Kappel; Sarah Schäfer; Matthias Wüst; Raymond E B Ketchum; Rodney B Croteau; Joaquim V Marques; Laurence B Davin; Norman G Lewis; Megan Rolf; Toni M Kutchan; D Doel Soejarto; B Markus Lange
Journal:  Phytochemistry       Date:  2013-04-16       Impact factor: 4.072

8.  From nature to the laboratory and into the clinic.

Authors:  K C Nicolaou; Jason S Chen; Stephen M Dalby
Journal:  Bioorg Med Chem       Date:  2008-11-06       Impact factor: 3.641

9.  Overview of major classes of plant-derived anticancer drugs.

Authors:  Amr Amin; Hala Gali-Muhtasib; Matthias Ocker; Regine Schneider-Stock
Journal:  Int J Biomed Sci       Date:  2009-03

10.  Engineering microbial cells for the biosynthesis of natural compounds of pharmaceutical significance.

Authors:  Philippe Jeandet; Yann Vasserot; Thomas Chastang; Eric Courot
Journal:  Biomed Res Int       Date:  2013-04-27       Impact factor: 3.411

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