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Amino Acids

, volume 43 , issue 4 , pages 1577-1591

2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε

Joachim Bischof ¹

Johann Leban ²

Mirko Zaja ²

Arnhild Grothey ^{1, 3}

Barbara Radunsky ¹

Olaf Othersen ²

Stefan Strobl ²

Daniel Vitt ²

Uwe Knippschild ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of General, Visceral and Transplantation Surgery, Surgery Centre, University of Ulm, Ulm, Germany |

Planegg-Martinsried, Germany |

Division of Surgery, Oncology, Reproductive Biology and Anaesthetics Hammersmith Campus, Imperial College, London, UK |

Publication type: Journal Article

Publication date: 2012-02-14

Springer Nature

Amino Acids

scimago Q1

wos Q3

SJR: 0.803

CiteScore: 6.8

Impact factor: 2.4

ISSN: 09394451, 14382199

DOI: 10.1007/s00726-012-1234-x

Copy DOI

PubMed ID: 22331384

Organic Chemistry

Biochemistry

Clinical Biochemistry

Abstract

In this study we identified two heterocyclic compounds (5 and 6) as potent and specific inhibitors of CK1δ (IC50 = 0.040 and 0.042 μM, respectively). Whereas compound 5 exhibited fivefold higher affinity towards CK1δ than to CK1ε (IC50 CK1ε = 0.199 μM), compound 6 also inhibited CK1ε (IC50 = 0.0326 μM) in the same range as CK1δ. Selected compound 5 was screened over 442 kinases identifying 5 as a highly potent and selective inhibitor of CK1δ. X-ray analysis of 5 bound to CK1δ demonstrated its binding mode. In addition, characterization of 5 and 6 in a cell biological approach revealed the ability of both compounds to inhibit proliferation of tumor cell lines in a dose and cell line specific manner. In summary, our optimizations lead to the development of new highly selective CK1δ and ε specific inhibitors with biological activity.

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GOST Copy

Bischof J. et al. 2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε // Amino Acids. 2012. Vol. 43. No. 4. pp. 1577-1591.

GOST all authors (up to 50) Copy

Bischof J., Leban J., Zaja M., Grothey A., Radunsky B., Othersen O., Strobl S., Vitt D., Knippschild U. 2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε // Amino Acids. 2012. Vol. 43. No. 4. pp. 1577-1591.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1007/s00726-012-1234-x

UR - https://doi.org/10.1007/s00726-012-1234-x

TI - 2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε

T2 - Amino Acids

AU - Bischof, Joachim

AU - Leban, Johann

AU - Zaja, Mirko

AU - Grothey, Arnhild

AU - Radunsky, Barbara

AU - Othersen, Olaf

AU - Strobl, Stefan

AU - Vitt, Daniel

AU - Knippschild, Uwe

PY - 2012

DA - 2012/02/14

PB - Springer Nature

SP - 1577-1591

IS - 4

VL - 43

PMID - 22331384

SN - 0939-4451

SN - 1438-2199

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2012_Bischof,

author = {Joachim Bischof and Johann Leban and Mirko Zaja and Arnhild Grothey and Barbara Radunsky and Olaf Othersen and Stefan Strobl and Daniel Vitt and Uwe Knippschild},

title = {2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε},

journal = {Amino Acids},

year = {2012},

volume = {43},

publisher = {Springer Nature},

month = {feb},

url = {https://doi.org/10.1007/s00726-012-1234-x},

number = {4},

pages = {1577--1591},

doi = {10.1007/s00726-012-1234-x}

}

MLA

Cite this

MLA Copy

Bischof, Joachim, et al. “2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε.” Amino Acids, vol. 43, no. 4, Feb. 2012, pp. 1577-1591. https://doi.org/10.1007/s00726-012-1234-x.

Publisher

Springer Nature

Journal

Amino Acids

scimago Q1

wos Q3

SJR

0.803

CiteScore

6.8

Impact factor

2.4

ISSN

09394451 (Print)

14382199 (Electronic)