Open AccessSynthesis of Hybrid Fluoroquinolone-Boron Complexes and Their Evaluation in Cervical Cancer Cell Lines
Author(s) -
Hiram HernándezLópez,
Griselda Sánchez-Miranda,
Jorge Gustavo Araujo-Huitrado,
Angélica Judith GranadosLópez,
Jesús Adrián López,
Socorro LeyvaRamos,
Luis ChacónGarcía
Publication year - 2019
Publication title -
journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.436
H-Index - 50
eISSN - 2090-9063
pISSN - 2090-9071
DOI - 10.1155/2019/5608652
Subject(s) - chemistry , dna gyrase , topoisomerase iv , topoisomerase , cell growth , boron , combinatorial chemistry , hela , cell culture , quinolone , apoptosis , pharmacology , enzyme , cell , antibiotics , biochemistry , escherichia coli , organic chemistry , medicine , genetics , biology , gene
Quinolones are a family of antimicrobial agents that have been used in antibacterial and anticancer chemotherapy. Fluoroquinolone targets DNA gyrase and topoisomerase IV enzymes affecting several cellular processes, like cell death and proliferation; the best way to act is in the form of carboxylic acid or, recently, as quinolone-metal complex. In this work, the use of boron is shown as an alternative of metal to form a complex by incorporating to fluoroquinolone as an electron withdrawing substituent to activate the C-7 position chemoselectively for the production of new fluoroquinolone hybrids and test their effects on cell proliferation. Fluoroquinolone-boron complexes were synthesized according to the Gould–Jacobs cyclization method, and five hybrid fluoroquinolone-boron compounds were obtained by S N Ar reaction, yielding 31 to 46%, at 80°C, and in 10 to 25 hours of reaction. The effect of the five fluoroquinolone-boron hybrids was evaluated in cervical cancer cell lines by cell proliferation assay. 7-hydantoin-fluoroquinolone-boron and 7-dihydropyridine-fluoroquinolone-boron complexes showed the strongest effect according to dose-response assay, respectively. The fluoroquinolone-boron hybrid complex showed proliferation inhibition in SiHa and CasKi cells, opening the possibility to use them as potential agents for the treatment of cancer.