Literature DB >> 28285914

Pharmacokinetic optimitzation of CCG-203971: Novel inhibitors of the Rho/MRTF/SRF transcriptional pathway as potential antifibrotic therapeutics for systemic scleroderma.

Kim M Hutchings1, Erika M Lisabeth2, Walajapet Rajeswaran1, Michael W Wilson1, Roderick J Sorenson1, Phillip L Campbell3, Jeffrey H Ruth3, Asif Amin3, Pei-Suen Tsou3, Jeffrey R Leipprandt2, Samuel R Olson2, Bo Wen4, Ting Zhao4, Duxin Sun4, Dinesh Khanna3, David A Fox3, Richard R Neubig2, Scott D Larsen5.   

Abstract

We recently reported the development of a novel inhibitor of Rho-mediated gene transcription (1, CCG-203971) that is efficacious in multiple animal models of acute fibrosis, including scleroderma, when given intraperitoneally. The modest in vivo potency and poor pharmacokinetics (PK) of this lead, however, make it unsuitable for long term efficacy studies. We therefore undertook a systematic medicinal chemistry effort to improve both the metabolic stability and the solubility of 1, resulting in the identification of two analogs achieving over 10-fold increases in plasma exposures in mice. We subsequently showed that one of these analogs (8f, CCG-232601) could inhibit the development of bleomycin-induced dermal fibrosis in mice when administered orally at 50mg/kg, an effect that was comparable to what we had observed earlier with 1 at a 4-fold higher IP dose.
Copyright © 2017 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antifibrotic; Fibrosis; MRTF; Myofibroblast; Rho; Scleroderma

Mesh:

Substances:

Year:  2017        PMID: 28285914      PMCID: PMC5395305          DOI: 10.1016/j.bmcl.2017.02.070

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


  18 in total

Review 1.  Emerging targets for the treatment of scleroderma.

Authors:  Andrew Leask
Journal:  Expert Opin Emerg Drugs       Date:  2012-04-25       Impact factor: 4.191

2.  Fibrosis under arrest.

Authors:  Thomas A Wynn
Journal:  Nat Med       Date:  2010-05       Impact factor: 53.440

3.  SMARTCyp: A 2D Method for Prediction of Cytochrome P450-Mediated Drug Metabolism.

Authors:  Patrik Rydberg; David E Gloriam; Jed Zaretzki; Curt Breneman; Lars Olsen
Journal:  ACS Med Chem Lett       Date:  2010-03-15       Impact factor: 4.345

4.  Ligand-Based Site of Metabolism Prediction for Cytochrome P450 2D6.

Authors:  Patrik Rydberg; Lars Olsen
Journal:  ACS Med Chem Lett       Date:  2011-11-07       Impact factor: 4.345

Review 5.  Linking actin dynamics and gene transcription to drive cellular motile functions.

Authors:  Eric N Olson; Alfred Nordheim
Journal:  Nat Rev Mol Cell Biol       Date:  2010-05       Impact factor: 94.444

6.  Novel Rho/MRTF/SRF inhibitors block matrix-stiffness and TGF-β-induced fibrogenesis in human colonic myofibroblasts.

Authors:  Laura A Johnson; Eva S Rodansky; Andrew J Haak; Scott D Larsen; Richard R Neubig; Peter D R Higgins
Journal:  Inflamm Bowel Dis       Date:  2014-01       Impact factor: 5.325

Review 7.  Cellular mechanisms of tissue fibrosis. 8. Current and future drug targets in fibrosis: focus on Rho GTPase-regulated gene transcription.

Authors:  Pei-Suen Tsou; Andrew J Haak; Dinesh Khanna; Richard R Neubig
Journal:  Am J Physiol Cell Physiol       Date:  2014-04-16       Impact factor: 4.249

8.  CCG-1423: a small-molecule inhibitor of RhoA transcriptional signaling.

Authors:  Chris R Evelyn; Susan M Wade; Qin Wang; Mei Wu; Jorge A Iñiguez-Lluhí; Sofia D Merajver; Richard R Neubig
Journal:  Mol Cancer Ther       Date:  2007-08       Impact factor: 6.261

9.  Targeting the myofibroblast genetic switch: inhibitors of myocardin-related transcription factor/serum response factor-regulated gene transcription prevent fibrosis in a murine model of skin injury.

Authors:  Andrew J Haak; Pei-Suen Tsou; Mohammad A Amin; Jeffrey H Ruth; Phillip Campbell; David A Fox; Dinesh Khanna; Scott D Larsen; Richard R Neubig
Journal:  J Pharmacol Exp Ther       Date:  2014-04-04       Impact factor: 4.030

10.  Local delivery of novel MRTF/SRF inhibitors prevents scar tissue formation in a preclinical model of fibrosis.

Authors:  Cynthia Yu-Wai-Man; Bradley Spencer-Dene; Richard M H Lee; Kim Hutchings; Erika M Lisabeth; Richard Treisman; Maryse Bailly; Scott D Larsen; Richard R Neubig; Peng T Khaw
Journal:  Sci Rep       Date:  2017-03-31       Impact factor: 4.379

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  19 in total

1.  Nucleocytoplasmic Shuttling of the Mechanosensitive Transcription Factors MRTF and YAP /TAZ.

Authors:  Michael Kofler; András Kapus
Journal:  Methods Mol Biol       Date:  2021

2.  Targeting MRTF/SRF in CAP2-dependent dilated cardiomyopathy delays disease onset.

Authors:  Yao Xiong; Kenneth Bedi; Simon Berritt; Bennette K Attipoe; Thomas G Brooks; Kevin Wang; Kenneth B Margulies; Jeffrey Field
Journal:  JCI Insight       Date:  2019-03-21

3.  Identification of Pirin as a Molecular Target of the CCG-1423/CCG-203971 Series of Antifibrotic and Antimetastatic Compounds.

Authors:  Erika M Lisabeth; Dylan Kahl; Indiwari Gopallawa; Sarah E Haynes; Sean A Misek; Phillip L Campbell; Thomas S Dexheimer; Dinesh Khanna; David A Fox; Xiangshu Jin; Brent R Martin; Scott D Larsen; Richard R Neubig
Journal:  ACS Pharmacol Transl Sci       Date:  2019-03-18

4.  Inhibition of EZH2 prevents fibrosis and restores normal angiogenesis in scleroderma.

Authors:  Pei-Suen Tsou; Phillip Campbell; M Asif Amin; Patrick Coit; Shaylynn Miller; David A Fox; Dinesh Khanna; Amr H Sawalha
Journal:  Proc Natl Acad Sci U S A       Date:  2019-02-12       Impact factor: 11.205

Review 5.  Mechanisms for the Resolution of Organ Fibrosis.

Authors:  Jeffrey C Horowitz; Victor J Thannickal
Journal:  Physiology (Bethesda)       Date:  2019-01-01

6.  5-Aryl-1,3,4-oxadiazol-2-ylthioalkanoic Acids: A Highly Potent New Class of Inhibitors of Rho/Myocardin-Related Transcription Factor (MRTF)/Serum Response Factor (SRF)-Mediated Gene Transcription as Potential Antifibrotic Agents for Scleroderma.

Authors:  Dylan J Kahl; Kim M Hutchings; Erika Mathes Lisabeth; Andrew J Haak; Jeffrey R Leipprandt; Thomas Dexheimer; Dinesh Khanna; Pei-Suen Tsou; Phillip L Campbell; David A Fox; Bo Wen; Duxin Sun; Marc Bailie; Richard R Neubig; Scott D Larsen
Journal:  J Med Chem       Date:  2019-04-18       Impact factor: 7.446

Review 7.  Mechanical regulation of chromatin and transcription.

Authors:  Sirio Dupont; Sara A Wickström
Journal:  Nat Rev Genet       Date:  2022-05-23       Impact factor: 59.581

8.  An injury-responsive Rac-to-Rho GTPase switch drives activation of muscle stem cells through rapid cytoskeletal remodeling.

Authors:  Allison P Kann; Margaret Hung; Wei Wang; Jo Nguyen; Penney M Gilbert; Zhuhao Wu; Robert S Krauss
Journal:  Cell Stem Cell       Date:  2022-05-20       Impact factor: 25.269

9.  Inhibition of the Myocardin-Related Transcription Factor Pathway Increases Efficacy of Trametinib in NRAS-Mutant Melanoma Cell Lines.

Authors:  Kathryn M Appleton; Charuta C Palsuledesai; Sean A Misek; Maja Blake; Joseph Zagorski; Kathleen A Gallo; Thomas S Dexheimer; Richard R Neubig
Journal:  Cancers (Basel)       Date:  2021-04-22       Impact factor: 6.639

Review 10.  MRTF: Basic Biology and Role in Kidney Disease.

Authors:  Maria Zena Miranda; Zsuzsanna Lichner; Katalin Szászi; András Kapus
Journal:  Int J Mol Sci       Date:  2021-06-03       Impact factor: 5.923

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