Literature DB >> 20676392

Confirmation of the Structures of Synthetic Derivatives of Migrastatin in the Light of Recently Disclosed Crystallographically Based Claims.

Pavel Nagorny1, Isaac Krauss, Jón T Njardarson, Lucy Perez, Christoph Gaul, Guangli Yang, Ouathek Ouerfelli, Samuel J Danishefsky.   

Abstract

In the light of recently disclosed crystallographic studies on migrastatin ketone 2 complex with fascin, the structures of migrastatin ketone 2 and migrastatin ether 4 have been re-evaluated by NMR and X-Ray crystallographic techniques. The results of these studies established the correctness of the previously reported structural assignment and confirm that the "small molecule" co-crystallized in complex with fascin is not the migrastatin ketone, which was provided for the infusion experiment, but rather its stereoisomer.

Entities:  

Year:  2010        PMID: 20676392      PMCID: PMC2910445          DOI: 10.1016/j.tetlet.2010.05.056

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  12 in total

1.  Migrastatin, a novel 14-membered lactone from Streptomyces sp. MK929-43F1.

Authors:  K Nakae; Y Yoshimoto; M Ueda; T Sawa; Y Takahashi; H Naganawa; T Takeuchi; M Imoto
Journal:  J Antibiot (Tokyo)       Date:  2000-10       Impact factor: 2.649

2.  Migrastatin, a new inhibitor of tumor cell migration from Streptomyces sp. MK929-43F1. Taxonomy, fermentation, isolation and biological activities.

Authors:  K Nakae; Y Yoshimoto; T Sawa; Y Homma; M Hamada; T Takeuchi; M Imoto
Journal:  J Antibiot (Tokyo)       Date:  2000-10       Impact factor: 2.649

3.  Migrastatin, a novel 14-membered ring macrolide, inhibits anchorage-independent growth of human small cell lung carcinoma Ms-1 cells.

Authors:  Y Takemoto; K Nakae; M Kawatani; Y Takahashi; H Naganawa; M Imoto
Journal:  J Antibiot (Tokyo)       Date:  2001-12       Impact factor: 2.649

4.  Absolute configuration of migrastatin, a novel 14-membered ring macrolide.

Authors:  Hikaru Nakamura; Yoshikazu Takahashi; Hiroshi Naganawa; Koichi Nakae; Masaya Imoto; Motoo Shiro; Koji Matsumura; Hidenori Watanabe; Takeshi Kitahara
Journal:  J Antibiot (Tokyo)       Date:  2002-04       Impact factor: 2.649

5.  Discovery of potent cell migration inhibitors through total synthesis: lessons from structure-activity studies of (+)-migrastatin.

Authors:  Jón T Njardarson; Christoph Gaul; Dandan Shan; Xin-Yun Huang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419

Review 6.  Chemistry and biology in search of antimetastatic agents.

Authors:  Lucy Pérez; Samuel J Danishefsky
Journal:  ACS Chem Biol       Date:  2007-03-20       Impact factor: 5.100

7.  Synthetic analogues of migrastatin that inhibit mammary tumor metastasis in mice.

Authors:  Dandan Shan; Lin Chen; Jon T Njardarson; Christoph Gaul; Xiaojing Ma; Samuel J Danishefsky; Xin-Yun Huang
Journal:  Proc Natl Acad Sci U S A       Date:  2005-02-22       Impact factor: 11.205

8.  Diverted total synthesis leads to the generation of promising cell-migration inhibitors for treatment of tumor metastasis: in vivo and mechanistic studies on the migrastatin core ether analog.

Authors:  Thordur Oskarsson; Pavel Nagorny; Isaac J Krauss; Lucy Perez; Mihirbaran Mandal; Guangli Yang; Ouathek Ouerfelli; Danhua Xiao; Malcolm A S Moore; Joan Massagué; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

Review 9.  Therapeutic targets for antimetastatic therapy.

Authors:  Benjamin D Hedley; Eric Winquist; Ann F Chambers
Journal:  Expert Opin Ther Targets       Date:  2004-12       Impact factor: 6.902

10.  Migrastatin analogues target fascin to block tumour metastasis.

Authors:  Lin Chen; Shengyu Yang; Jean Jakoncic; J Jillian Zhang; Xin-Yun Huang
Journal:  Nature       Date:  2010-04-15       Impact factor: 49.962

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  6 in total

1.  Emergence of potent inhibitors of metastasis in lung cancer via syntheses based on migrastatin.

Authors:  Nicolas Lecomte; Jon T Njardarson; Pavel Nagorny; Guangli Yang; Robert Downey; Ouathek Ouerfelli; Malcolm A S Moore; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2011-08-01       Impact factor: 11.205

2.  Multifaceted modes of action for the glutarimide-containing polyketides revealed.

Authors:  Scott R Rajski; Ben Shen
Journal:  Chembiochem       Date:  2010-09-24       Impact factor: 3.164

3.  Post-polyketide synthase steps in iso-migrastatin biosynthesis, featuring tailoring enzymes with broad substrate specificity.

Authors:  Ming Ma; Thomas Kwong; Si-Kyu Lim; Jianhua Ju; Jeremy R Lohman; Ben Shen
Journal:  J Am Chem Soc       Date:  2013-02-11       Impact factor: 15.419

4.  Tunneling nanotubes provide a unique conduit for intercellular transfer of cellular contents in human malignant pleural mesothelioma.

Authors:  Emil Lou; Sho Fujisawa; Alexei Morozov; Afsar Barlas; Yevgeniy Romin; Yildirim Dogan; Sepideh Gholami; André L Moreira; Katia Manova-Todorova; Malcolm A S Moore
Journal:  PLoS One       Date:  2012-03-09       Impact factor: 3.240

Review 5.  The Therapeutic Potential of Migrastatin-Core Analogs for the Treatment of Metastatic Cancer.

Authors:  Ernest Giralt; Daniele Lo Re
Journal:  Molecules       Date:  2017-02-09       Impact factor: 4.411

Review 6.  Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.

Authors:  Erika A Crane; Karl Gademann
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

  6 in total

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