Bioorganic and Medicinal Chemistry

, volume 18 , issue 7 , pages 2375-2387

Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies

Bojan Burja ¹

Tamara Čimbora Zovko ²

S. Tomic ³

Tihana Jelušić ²

Marijan Kocevar ¹

Slovenko Polanc ¹

Maja Osmak ²

Hide authors affiliations Show authors affiliations: 3 affiliations

Faculty of Chemistry and Chemical Technology, University of Ljubljana , Aškerčeva 5, SI-1000, Ljubljana, Slovenia. |

Division of Molecular Biology, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia |

Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia |

Publication type: Journal Article

Publication date: 2010-04-01

Elsevier

Bioorganic and Medicinal Chemistry

scimago Q2

wos Q1

SJR: 0.608

CiteScore: 6.7

Impact factor: 3.0

ISSN: 09680896, 14643391

DOI: 10.1016/j.bmc.2010.03.006

Copy DOI

PubMed ID: 20338766

Organic Chemistry

Drug Discovery

Biochemistry

Molecular Biology

Pharmaceutical Science

Clinical Biochemistry

Molecular Medicine

Abstract

A series of pyrazolone-fused combretastatins and precursors were synthesized and their cytotoxicity as well as antitubulin potential was evaluated. The hydrazide 9f and the pyrazolone-fused combretastatins 12a, 12b and 12c were highly cytotoxic against various tumor cell lines including cisplatin resistant cells. The same compounds were also the best inhibitors of tubulin polymerization. Molecular modeling results showed that they bind the colchicine binding site at the tubulin heterodimer. The hydrazide 9f arrested HeLa cells in the G2/M phase of the cell cycle and strongly affected cell shape and microtubule network.

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Abdelhamid Dalia

35 publications, 1 301 citations, 15 reviews

h-index: 22

Minia University

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Alberto Luis

842 publications, 26 290 citations

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GOST |

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GOST Copy

Burja B. et al. Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies // Bioorganic and Medicinal Chemistry. 2010. Vol. 18. No. 7. pp. 2375-2387.

GOST all authors (up to 50) Copy

Burja B., Čimbora Zovko T., Tomic S., Jelušić T., Kocevar M., Polanc S., Osmak M. Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies // Bioorganic and Medicinal Chemistry. 2010. Vol. 18. No. 7. pp. 2375-2387.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.bmc.2010.03.006

UR - https://doi.org/10.1016/j.bmc.2010.03.006

TI - Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies

T2 - Bioorganic and Medicinal Chemistry

AU - Burja, Bojan

AU - Čimbora Zovko, Tamara

AU - Tomic, S.

AU - Jelušić, Tihana

AU - Kocevar, Marijan

AU - Polanc, Slovenko

AU - Osmak, Maja

PY - 2010

DA - 2010/04/01

PB - Elsevier

SP - 2375-2387

IS - 7

VL - 18

PMID - 20338766

SN - 0968-0896

SN - 1464-3391

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2010_Burja,

author = {Bojan Burja and Tamara Čimbora Zovko and S. Tomic and Tihana Jelušić and Marijan Kocevar and Slovenko Polanc and Maja Osmak},

title = {Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies},

journal = {Bioorganic and Medicinal Chemistry},

year = {2010},

volume = {18},

publisher = {Elsevier},

month = {apr},

url = {https://doi.org/10.1016/j.bmc.2010.03.006},

number = {7},

pages = {2375--2387},

doi = {10.1016/j.bmc.2010.03.006}

}

MLA

Cite this

MLA Copy

Burja, Bojan, et al. “Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies.” Bioorganic and Medicinal Chemistry, vol. 18, no. 7, Apr. 2010, pp. 2375-2387. https://doi.org/10.1016/j.bmc.2010.03.006.

Publisher

Elsevier

Journal

Bioorganic and Medicinal Chemistry

scimago Q2

wos Q1

SJR

0.608

CiteScore

6.7

Impact factor

3.0

ISSN

09680896 (Print)

14643391 (Electronic)