Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase i and II inhibitory activity

Mohamed Abdel-Aziz; So Eun Park; Gamal El Din A.A. Abuo-Rahma; Mohamed A. Sayed; Youngjoo Kwon

doi:10.1016/j.ejmech.2013.08.040

Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase i and II inhibitory activity

Mohamed Abdel-Aziz, So Eun Park, Gamal El Din A.A. Abuo-Rahma, Mohamed A. Sayed, Youngjoo Kwon

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

117 Scopus citations

Abstract

A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI₅₀ level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 μM and 20 μM concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 μM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 μM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a-j compared to the parent ciprofloxacin.

Original language	English
Pages (from-to)	427-438
Number of pages	12
Journal	European Journal of Medicinal Chemistry
Volume	69
DOIs	https://doi.org/10.1016/j.ejmech.2013.08.040
State	Published - 2013

Bibliographical note

Funding Information:
Authors thank the Development Therapeutics Program of the National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity. This work was funded by the Faculty of Pharmacy, Minia University, Minia, Egypt (Chemistry, Physicochemical properties) and by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2010-0002646 ) (for topoisomerase I & II inhibitory activities measurement).

Keywords

Anti-tumor
Chalcone
Ciprofloxacin
Hybrids
Topoisomerase

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10.1016/j.ejmech.2013.08.040

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title = "Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase i and II inhibitory activity",

abstract = "A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI50 level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 μM and 20 μM concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 μM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 μM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a-j compared to the parent ciprofloxacin.",

keywords = "Anti-tumor, Chalcone, Ciprofloxacin, Hybrids, Topoisomerase",

author = "Mohamed Abdel-Aziz and Park, {So Eun} and Abuo-Rahma, {Gamal El Din A.A.} and Sayed, {Mohamed A.} and Youngjoo Kwon",

note = "Funding Information: Authors thank the Development Therapeutics Program of the National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity. This work was funded by the Faculty of Pharmacy, Minia University, Minia, Egypt (Chemistry, Physicochemical properties) and by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2010-0002646 ) (for topoisomerase I & II inhibitory activities measurement). ",

year = "2013",

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volume = "69",

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AU - Abdel-Aziz, Mohamed

AU - Park, So Eun

AU - Abuo-Rahma, Gamal El Din A.A.

AU - Sayed, Mohamed A.

AU - Kwon, Youngjoo

N1 - Funding Information: Authors thank the Development Therapeutics Program of the National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity. This work was funded by the Faculty of Pharmacy, Minia University, Minia, Egypt (Chemistry, Physicochemical properties) and by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2010-0002646 ) (for topoisomerase I & II inhibitory activities measurement).

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Y1 - 2013

N2 - A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI50 level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 μM and 20 μM concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 μM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 μM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a-j compared to the parent ciprofloxacin.

AB - A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI50 level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 μM and 20 μM concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 μM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 μM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a-j compared to the parent ciprofloxacin.

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KW - Hybrids

KW - Topoisomerase

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ER -

Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase i and II inhibitory activity

Abstract

Bibliographical note

Keywords

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