Literature DB >> 24900510

Diaminopyridine-based potent and selective mps1 kinase inhibitors binding to an unusual flipped-Peptide conformation.

Ken-Ichi Kusakabe1, Nobuyuki Ide1, Yataro Daigo2, Takeshi Itoh1, Kenichi Higashino1, Yousuke Okano1, Genta Tadano1, Yuki Tachibana1, Yuji Sato1, Makiko Inoue1, Tooru Wada1, Motofumi Iguchi1, Takayuki Kanazawa1, Yukichi Ishioka1, Keiji Dohi1, Sachie Tagashira1, Yasuto Kido1, Shingo Sakamoto1, Kazuya Yasuo1, Masahiro Maeda1, Takahiko Yamamoto1, Masayo Higaki1, Takeshi Endoh1, Kazuo Ueda1, Takeshi Shiota1, Hitoshi Murai1, Yusuke Nakamura3.   

Abstract

Monopolar spindle 1 (Mps1) is an attractive cancer drug target due to the important role that it plays in centrosome duplication, the spindle assembly checkpoint, and the maintenance of chromosomal stability. A design based on JNK inhibitors with an aminopyridine scaffold and subsequent modifications identified diaminopyridine 9 with an IC50 of 37 nM. The X-ray structure of 9 revealed that the Cys604 carbonyl group of the hinge region flips to form a hydrogen bond with the aniline NH group in 9. Further optimization of 9 led to 12 with improved cellular activity, suitable pharmacokinetic profiles, and good in vivo efficacy in the mouse A549 xenograft model. Moreover, 12 displayed excellent selectivity over 95 kinases, indicating the contribution of its unusual flipped-peptide conformation to its selectivity.

Entities:  

Keywords:  Mps 1; TTK; cancer; diaminopyridine; inhibitor; monopolar spindle 1; peptide flip

Year:  2012        PMID： 24900510      PMCID： PMC4025729          DOI： 10.1021/ml3000879

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  25 in total

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2.  Ablation of the spindle assembly checkpoint by a compound targeting Mps1.

Authors:  Marc Schmidt; Yemima Budirahardja; Rob Klompmaker; René H Medema
Journal:  EMBO Rep       Date:  2005-09       Impact factor: 8.807

3.  Assessment of chemical coverage of kinome space and its implications for kinase drug discovery.

Authors:  Paul Bamborough; David Drewry; Gavin Harper; Gary K Smith; Klaus Schneider
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4.  Design and synthesis of potent, orally bioavailable dihydroquinazolinone inhibitors of p38 MAP kinase.

Authors:  John E Stelmach; Luping Liu; Sangita B Patel; James V Pivnichny; Giovanna Scapin; Suresh Singh; Cornelis E C A Hop; Zhen Wang; John R Strauss; Patricia M Cameron; Elizabeth A Nichols; Stephen J O'Keefe; Edward A O'Neill; Dennis M Schmatz; Cheryl D Schwartz; Chris M Thompson; Dennis M Zaller; James B Doherty
Journal:  Bioorg Med Chem Lett       Date:  2003-01-20       Impact factor: 2.823

5.  High levels of the Mps1 checkpoint protein are protective of aneuploidy in breast cancer cells.

Authors:  Jewel Daniel; Jonathan Coulter; Ju-Hyung Woo; Kathleen Wilsbach; Edward Gabrielson
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-14       Impact factor: 11.205

6.  Synthesis and SAR of new pyrazolo[4,3-h]quinazoline-3-carboxamide derivatives as potent and selective MPS1 kinase inhibitors.

Authors:  Marina Caldarelli; Mauro Angiolini; Teresa Disingrini; Daniele Donati; Marco Guanci; Stefano Nuvoloni; Helena Posteri; Francesca Quartieri; Marco Silvagni; Riccardo Colombo
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7.  Characterization of the cellular and antitumor effects of MPI-0479605, a small-molecule inhibitor of the mitotic kinase Mps1.

Authors:  Keith D Tardif; Aaron Rogers; Jared Cassiano; Bruce L Roth; Daniel M Cimbora; Rena McKinnon; Ashley Peterson; Thomas B Douce; Rosann Robinson; Irene Dorweiler; Thaylon Davis; Mark A Hess; Kirill Ostanin; Damon I Papac; Vijay Baichwal; Ian McAlexander; J Adam Willardsen; Michael Saunders; Hoarau Christophe; D Vijay Kumar; Daniel A Wettstein; Robert O Carlson; Brandi L Williams
Journal:  Mol Cancer Ther       Date:  2011-10-06       Impact factor: 6.261

8.  Expression profiles of non-small cell lung cancers on cDNA microarrays: identification of genes for prediction of lymph-node metastasis and sensitivity to anti-cancer drugs.

Authors:  Takefumi Kikuchi; Yataro Daigo; Toyomasa Katagiri; Tatsuhiko Tsunoda; Koichi Okada; Soji Kakiuchi; Hitoshi Zembutsu; Yoichi Furukawa; Masafumi Kawamura; Koichi Kobayashi; Kohzoh Imai; Yusuke Nakamura
Journal:  Oncogene       Date:  2003-04-10       Impact factor: 9.867

9.  Targeting the mitotic checkpoint for cancer therapy with NMS-P715, an inhibitor of MPS1 kinase.

Authors:  Riccardo Colombo; Marina Caldarelli; Milena Mennecozzi; Maria Laura Giorgini; Francesco Sola; Paolo Cappella; Claudia Perrera; Stefania Re Depaolini; Luisa Rusconi; Ulisse Cucchi; Nilla Avanzi; Jay Aaron Bertrand; Roberto Tiberio Bossi; Enrico Pesenti; Arturo Galvani; Antonella Isacchi; Francesco Colotta; Daniele Donati; Jürgen Moll
Journal:  Cancer Res       Date:  2010-12-15       Impact factor: 12.701

10.  Structural bioinformatics-based prediction of exceptional selectivity of p38 MAP kinase inhibitor PH-797804.

Authors:  Li Xing; Huey S Shieh; Shaun R Selness; Rajesh V Devraj; John K Walker; Balekudru Devadas; Heidi R Hope; Robert P Compton; John F Schindler; Jeffrey L Hirsch; Alan G Benson; Ravi G Kurumbail; Roderick A Stegeman; Jennifer M Williams; Richard M Broadus; Zara Walden; Joseph B Monahan
Journal:  Biochemistry       Date:  2009-07-14       Impact factor: 3.162
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  7 in total

1.  TC Mps1 12, a novel Mps1 inhibitor, suppresses the growth of hepatocellular carcinoma cells via the accumulation of chromosomal instability.

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Journal:  Br J Pharmacol       Date:  2017-04-22       Impact factor: 8.739

Review 2.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

3.  Mitotic Checkpoint Kinase Mps1 Has a Role in Normal Physiology which Impacts Clinical Utility.

Authors:  Ricardo Martinez; Alessandra Blasina; Jill F Hallin; Wenyue Hu; Isha Rymer; Jeffery Fan; Robert L Hoffman; Sean Murphy; Matthew Marx; Gina Yanochko; Dusko Trajkovic; Dac Dinh; Sergei Timofeevski; Zhou Zhu; Peiquing Sun; Patrick B Lappin; Brion W Murray
Journal:  PLoS One       Date:  2015-09-23       Impact factor: 3.240

4.  Structure-based design of orally bioavailable 1H-pyrrolo[3,2-c]pyridine inhibitors of mitotic kinase monopolar spindle 1 (MPS1).

Authors:  Sébastien Naud; Isaac M Westwood; Amir Faisal; Peter Sheldrake; Vassilios Bavetsias; Butrus Atrash; Kwai-Ming J Cheung; Manjuan Liu; Angela Hayes; Jessica Schmitt; Amy Wood; Vanessa Choi; Kathy Boxall; Grace Mak; Mark Gurden; Melanie Valenti; Alexis de Haven Brandon; Alan Henley; Ross Baker; Craig McAndrew; Berry Matijssen; Rosemary Burke; Swen Hoelder; Suzanne A Eccles; Florence I Raynaud; Spiros Linardopoulos; Rob L M van Montfort; Julian Blagg
Journal:  J Med Chem       Date:  2013-12-02       Impact factor: 7.446

5.  Mps1 inhibitors synergise with low doses of taxanes in promoting tumour cell death by enhancement of errors in cell division.

Authors:  Ana Rita R Maia; Simon Linder; Ji-Ying Song; Chantal Vaarting; Ute Boon; Colin E J Pritchard; Arno Velds; Ivo J Huijbers; Olaf van Tellingen; Jos Jonkers; René H Medema
Journal:  Br J Cancer       Date:  2018-05-08       Impact factor: 7.640

6.  Development of Novel In Vivo Chemical Probes to Address CNS Protein Kinase Involvement in Synaptic Dysfunction.

Authors:  D Martin Watterson; Valerie L Grum-Tokars; Saktimayee M Roy; James P Schavocky; Brinda Desai Bradaric; Adam D Bachstetter; Bin Xing; Edgardo Dimayuga; Faisal Saeed; Hong Zhang; Agnieszka Staniszewski; Jeffrey C Pelletier; George Minasov; Wayne F Anderson; Ottavio Arancio; Linda J Van Eldik
Journal:  PLoS One       Date:  2013-06-26       Impact factor: 3.240

7.  Scaffold-focused virtual screening: prospective application to the discovery of TTK inhibitors.

Authors:  Sarah R Langdon; Isaac M Westwood; Rob L M van Montfort; Nathan Brown; Julian Blagg
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  7 in total

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