Literature DB >> 23457660

Developing novel C-4 analogues of pyrrole-based antitubulin agents: weak but critical hydrogen bonding in the colchicine site.

Chenxiao Da1, Nakul Telang2, Kayleigh Hall2, Emily Kluball2, Peter Barelli2, Kara Finzel2, Xin Jia2, John T Gupton2, Susan L Mooberry3, Glen E Kellogg1.   

Abstract

The synthesis, biological evaluation and molecular modeling of a series of pyrrole compounds related to 3,5-dibromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid that evaluates and optimizes C-4 substituents are reported. The key factor for microtubule depolymerization activity appears to be the presence of an appropriately positioned acceptor for Cys241β in the otherwise hydrophobic subpocket A.

Entities:  

Year:  2013        PMID： 23457660      PMCID： PMC3583212          DOI： 10.1039/C2MD20320K

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  16 in total

1.  Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain.

Authors:  Raimond B G Ravelli; Benoît Gigant; Patrick A Curmi; Isabelle Jourdain; Sylvie Lachkar; André Sobel; Marcel Knossow
Journal:  Nature       Date:  2004-03-11       Impact factor: 49.962

2.  Pyrrole-Based Antitubulin Agents: Two Distinct Binding Modalities are Predicted for C-2 Analogs in the Colchicine Site.

Authors:  Chenxiao Da; Nakul Telang; Peter Barelli; Xin Jia; John T Gupton; Susan L Mooberry; Glen E Kellogg
Journal:  ACS Med Chem Lett       Date:  2011-11-01       Impact factor: 4.345

Review 3.  Targeting tumour vasculature: the development of combretastatin A4.

Authors:  J Griggs; J C Metcalfe; R Hesketh
Journal:  Lancet Oncol       Date:  2001-02       Impact factor: 41.316

4.  Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation.

Authors:  G Jones; P Willett; R C Glen
Journal:  J Mol Biol       Date:  1995-01-06       Impact factor: 5.469

5.  Synthesis and cytotoxicity of 2,4-disubstituted and 2,3,4-trisubstituted brominated pyrroles in murine and human cultured tumor cells.

Authors:  J T Gupton; B S Burham; K Krumpe; K Du; J A Sikorski; A E Warren; C R Barnes; I H Hall
Journal:  Arch Pharm (Weinheim)       Date:  2000-01       Impact factor: 3.751

Review 6.  Microtubule-binding agents: a dynamic field of cancer therapeutics.

Authors:  Charles Dumontet; Mary Ann Jordan
Journal:  Nat Rev Drug Discov       Date:  2010-10       Impact factor: 84.694

7.  Class III beta-tubulin expression and in vitro resistance to microtubule targeting agents.

Authors:  C Stengel; S P Newman; M P Leese; B V L Potter; M J Reed; A Purohit
Journal:  Br J Cancer       Date:  2009-12-22       Impact factor: 7.640

8.  Identification and characterization of a new tubulin-binding tetrasubstituted brominated pyrrole.

Authors:  Susan L Mooberry; Kimberly N Weiderhold; Sivanesan Dakshanamurthy; Ernest Hamel; Edith J Banner; Anastasia Kharlamova; Jonathan Hempel; John T Gupton; Milton L Brown
Journal:  Mol Pharmacol       Date:  2007-04-24       Impact factor: 4.436

Review 9.  Recent development and SAR analysis of colchicine binding site inhibitors.

Authors:  Jing Chen; Tao Liu; Xiaowu Dong; Yongzhou Hu
Journal:  Mini Rev Med Chem       Date:  2009-09       Impact factor: 3.862

10.  Docking and hydropathic scoring of polysubstituted pyrrole compounds with antitubulin activity.

Authors:  Ashutosh Tripathi; Micaela Fornabaio; Glen E Kellogg; John T Gupton; David A Gewirtz; W Andrew Yeudall; Nina E Vega; Susan L Mooberry
Journal:  Bioorg Med Chem       Date:  2007-12-04       Impact factor: 3.641
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  9 in total

1.  A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction.

Authors:  Satheesh Gujarathi; Xingui Liu; Lin Song; Howard Hendrickson; Guangrong Zheng
Journal:  Tetrahedron       Date:  2014-08-26       Impact factor: 2.457

2.  Structures of potent anticancer compounds bound to tubulin.

Authors:  Dan E McNamara; Silvia Senese; Todd O Yeates; Jorge Z Torres
Journal:  Protein Sci       Date:  2015-05-27       Impact factor: 6.725

3.  Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities.

Authors:  John T Gupton; Scott Yeudall; Nakul Telang; Megan Hoerrner; Ellis Huff; Evan Crawford; Katie Lounsbury; Michael Kimmel; William Curry; Andrew Harrison; Wen Juekun; Alex Shimozono; Joe Ortolani; Kristin Lescalleet; Jon Patteson; Veronica Moore-Stoll; Cristina C Rohena; Susan L Mooberry; Ahmad J Obaidullah; Glen E Kellogg; James A Sikorski
Journal:  Bioorg Med Chem       Date:  2017-04-11       Impact factor: 3.641

4.  Biological Characterization of an Improved Pyrrole-Based Colchicine Site Agent Identified through Structure-Based Design.

Authors:  Cristina C Rohena; Nakul S Telang; Chenxiao Da; April L Risinger; James A Sikorski; Glen E Kellogg; John T Gupton; Susan L Mooberry
Journal:  Mol Pharmacol       Date:  2015-12-11       Impact factor: 4.436

5.  How to deal with low-resolution target structures: using SAR, ensemble docking, hydropathic analysis, and 3D-QSAR to definitively map the αβ-tubulin colchicine site.

Authors:  Chenxiao Da; Susan L Mooberry; John T Gupton; Glen E Kellogg
Journal:  J Med Chem       Date:  2013-09-09       Impact factor: 7.446

6.  Effects of a pyrrole-based, microtubule-depolymerizing compound on RAW 264.7 macrophages.

Authors:  John A Ciemniecki; Clarke P Lewis; John T Gupton; Krista Fischer-Stenger
Journal:  Chem Biol Interact       Date:  2016-01-11       Impact factor: 5.192

7.  Effects of a novel microtubule-depolymerizer on pro-inflammatory signaling in RAW264.7 macrophages.

Authors:  Samuel P Gilmore; Anna L K Gonye; Elizabeth C Li; Santiago Espinosa de Los Reyes; John T Gupton; Omar A Quintero; Krista Fischer-Stenger
Journal:  Chem Biol Interact       Date:  2017-12-13       Impact factor: 5.192

8.  Structure-activity relationships of retro-dihydrochalcones isolated from Tacca sp.

Authors:  Jiangnan Peng; April L Risinger; Chenxiao Da; Gary A Fest; Glen E Kellogg; Susan L Mooberry
Journal:  J Nat Prod       Date:  2013-12-04       Impact factor: 4.050

9.  Synthesis and Anticancer Activity of Mitotic-Specific 3,4-Dihydropyridine-2(1H)-thiones.

Authors:  Magdalena Perużyńska; Aleksandra Borzyszkowska-Ledwig; Jacek G Sośnicki; Łukasz Struk; Tomasz J Idzik; Gabriela Maciejewska; Łukasz Skalski; Katarzyna Piotrowska; Paweł Łukasik; Marek Droździk; Mateusz Kurzawski
Journal:  Int J Mol Sci       Date:  2021-02-28       Impact factor: 5.923
  9 in total

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