Literature DB >> 18684620

Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency.

Jianhua Ju1, Scott R Rajski, Si-Kyu Lim, Jeong-Woo Seo, Noël R Peters, F Michael Hoffmann, Ben Shen.   

Abstract

Lactimidomycin (LTM, 1), iso-migrastatin (iso-MGS, 2) and migrastatin (MGS, 3) are macrolide antitumor antibiotics differing in macrolide ring size but all bearing a glutarimide side chain. To further develop these natural products and related analogs as drug candidates we have produced and evaluated the biological activities of a small library of iso-MGS and LTM-derived agents; congeners evaluated bear either the MGS scaffold or related acyclic (dorrigocin) scaffolds. Scratch wound-healing (SWH) assays with 4T1 mouse and MDA-MB-231 human mammary tumor cell lines, respectively, reveal structural elements crucial to inhibition of cell migration by these compounds. Moreover, two substances, 14 and 17, with activity far superior to that of MGS are unveiled by SWH assays.

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Year:  2008        PMID： 18684620      PMCID： PMC2585373          DOI： 10.1016/j.bmcl.2008.07.072

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  21 in total

1.  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

2.  NK30424A and B, novel inhibitors of lipopolysaccharide-induced tumour necrosis factor alpha production, produced by Streptomyces sp. NA30424.

Authors:  Y Takayasu; K Tsuchiya; T Aoyama; Y Sukenaga
Journal:  J Antibiot (Tokyo)       Date:  2001-12       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.  Oxidative modification of NK30424A and B enhance inhibitory effect on lipopolysaccharide-induced tumour necrosis factor-alpha promoter activity.

Authors:  Yoshiyuki Takayasu; Kouichi Tsuchiya; Yoshikazu Sukenaga
Journal:  J Antibiot (Tokyo)       Date:  2002-03       Impact factor: 2.649

5.  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

6.  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

7.  Migrastatin and a new compound, isomigrastatin, from Streptomyces platensis.

Authors:  Elaine J Woo; Courtney M Starks; John R Carney; Robert Arslanian; Lawrence Cadapan; Stefan Zavala; Peter Licari
Journal:  J Antibiot (Tokyo)       Date:  2002-02       Impact factor: 2.649

8.  Isolation, antifungal activity, and structure elucidation of the glutarimide antibiotic, streptimidone, produced by Micromonospora coerulea.

Authors:  B S Kim; S S Moon; B K Hwang
Journal:  J Agric Food Chem       Date:  1999-08       Impact factor: 5.279

9.  New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus.

Authors:  Jianhua Ju; Jeong-Woo Seo; Yeng Her; Si-Kyu Lim; Ben Shen
Journal:  Org Lett       Date:  2007-11-13       Impact factor: 6.005

10.  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
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  11 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

2.  Titer improvement of iso-migrastatin in selected heterologous Streptomyces hosts and related analysis of mRNA expression by quantitative RT-PCR.

Authors:  Dong Yang; Xiangcheng Zhu; Xueyun Wu; Zhiyang Feng; Lei Huang; Ben Shen; Zhinan Xu
Journal:  Appl Microbiol Biotechnol       Date:  2010-12-04       Impact factor: 4.813

3.  A Long-Range Acting Dehydratase Domain as the Missing Link for C17-Dehydration in Iso-Migrastatin Biosynthesis.

Authors:  Bo Zhang; Zhengren Xu; Qihui Teng; Guohui Pan; Ming Ma; Ben Shen
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

4.  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

5.  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

6.  Lactimidomycin, iso-migrastatin and related glutarimide-containing 12-membered macrolides are extremely potent inhibitors of cell migration.

Authors:  Jianhua Ju; Scott R Rajski; Si-Kyu Lim; Jeong-Woo Seo; Noël R Peters; F Michael Hoffmann; Ben Shen
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

7.  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

8.  iso-Migrastatin, migrastatin, and dorrigocin production in Streptomyces platensis NRRL 18993 is governed by a single biosynthetic machinery featuring an acyltransferase-less type I polyketide synthase.

Authors:  Si-Kyu Lim; Jianhua Ju; Emmanuel Zazopoulos; Hui Jiang; Jeong-Woo Seo; Yihua Chen; Zhiyang Feng; Scott R Rajski; Chris M Farnet; Ben Shen
Journal:  J Biol Chem       Date:  2009-09-02       Impact factor: 5.157

9.  Overproduction of lactimidomycin by cross-overexpression of genes encoding Streptomyces antibiotic regulatory proteins.

Authors:  Bo Zhang; Dong Yang; Yijun Yan; Guohui Pan; Wensheng Xiang; Ben Shen
Journal:  Appl Microbiol Biotechnol       Date:  2015-11-10       Impact factor: 4.813

10.  Migrastatin analogues inhibit canine mammary cancer cell migration and invasion.

Authors:  Kinga Majchrzak; Daniele Lo Re; Małgorzata Gajewska; Małgorzata Bulkowska; Agata Homa; Karol Pawłowski; Tomasz Motyl; Paul V Murphy; Magdalena Król
Journal:  PLoS One       Date:  2013-10-08       Impact factor: 3.240
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