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Literature DB >> 20155906

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.

Thordur Oskarsson¹, Pavel Nagorny, Isaac J Krauss, Lucy Perez, Mihirbaran Mandal, Guangli Yang, Ouathek Ouerfelli, Danhua Xiao, Malcolm A S Moore, Joan Massagué, Samuel J Danishefsky.

Abstract

A significantly simpler analog of the natural product migrastatin, termed migrastatin ether (ME), has been prepared and evaluated. Both in vivo and in vitro studies indicate that ME exhibits a concentration-dependent inhibitory effect on migration of breast cancer cells.

Entities: CellLine Chemical Disease Gene Species

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Year: 2010 PMID： 20155906 PMCID： PMC2863049 DOI： 10.1021/ja9101503

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

21 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 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

3. 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

4. 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

5. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors: M Scholl; S Ding; C W Lee; R H Grubbs
Journal: Org Lett Date: 1999-09-23 Impact factor: 6.005

6. Distinct organ-specific metastatic potential of individual breast cancer cells and primary tumors.

Authors: Andy J Minn; Yibin Kang; Inna Serganova; Gaorav P Gupta; Dilip D Giri; Mikhail Doubrovin; Vladimir Ponomarev; William L Gerald; Ronald Blasberg; Joan Massagué
Journal: J Clin Invest Date: 2005-01 Impact factor: 14.808

Review 7. 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

8. The migrastatin family: discovery of potent cell migration inhibitors by chemical synthesis.

Authors: Christoph Gaul; Jón T Njardarson; Dandan Shan; David C Dorn; Kai-Da Wu; William P Tong; Xin-Yun Huang; Malcolm A S Moore; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2004-09-15 Impact factor: 15.419

9. The total synthesis of (+)-migrastatin.

Authors: Christoph Gaul; Jon T Njardarson; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

10. Tumor self-seeding by circulating cancer cells.

Authors: Mi-Young Kim; Thordur Oskarsson; Swarnali Acharyya; Don X Nguyen; Xiang H-F Zhang; Larry Norton; Joan Massagué
Journal: Cell Date: 2009-12-24 Impact factor: 41.582

17 in total

1. Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones.

Authors: Anniefer N Magpusao; Richard T Desmond; Katelyn J Billings; Gabriel Fenteany; Mark W Peczuh
Journal: Bioorg Med Chem Lett Date: 2010-07-25 Impact factor: 2.823

Review 2. Tumor metastasis: molecular insights and evolving paradigms.

Authors: Scott Valastyan; Robert A Weinberg
Journal: Cell Date: 2011-10-14 Impact factor: 41.582

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

Authors: Pavel Nagorny; Isaac Krauss; Jón T Njardarson; Lucy Perez; Christoph Gaul; Guangli Yang; Ouathek Ouerfelli; Samuel J Danishefsky
Journal: Tetrahedron Lett Date: 2010-07-28 Impact factor: 2.415

4. Synthetic studies toward (+)-cortistatin A.

Authors: Zhang Wang; Mingji Dai; Peter K Park; Samuel J Danishefsky
Journal: Tetrahedron Date: 2011-10-29 Impact factor: 2.457

5. The enantioselective synthesis and biological evaluation of chimeric promysalin analogs facilitated by diverted total synthesis.

Authors: Kyle W Knouse; William M Wuest
Journal: J Antibiot (Tokyo) Date: 2016-02-10 Impact factor: 2.649

Review 6. Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

Authors: Jeffrey S Cannon; Larry E Overman
Journal: Angew Chem Int Ed Engl Date: 2012-03-19 Impact factor: 15.336

10. 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