Abstract
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 SNAr 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.
Highlights
Hiram Hernandez-Lopez,1 Griselda Sanchez-Miranda,1 Jorge Gustavo Araujo-Huitrado,2 Angelica Judith Granados-Lopez,2,3 Jesus Adrian Lopez,1,2 Socorro Leyva-Ramos,4 and Luis Chacon-Garcıa 5
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
Fluoroquinolone-boron complexes were synthesized according to the Gould–Jacobs cyclization method, and five hybrid fluoroquinolone-boron compounds were obtained by SNAr reaction, yielding 31 to 46%, at 80°C, and in 10 to 25 hours of reaction. e 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. e 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
Summary
Hiram Hernandez-Lopez ,1 Griselda Sanchez-Miranda, Jorge Gustavo Araujo-Huitrado, Angelica Judith Granados-Lopez, Jesus Adrian Lopez ,1,2 Socorro Leyva-Ramos, and Luis Chacon-Garcıa 5. 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. E 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. Studies of fluoroquinolone complexed with copper (II), iron, palladium, platinum, and bismuth were found to have higher antibacterial activity than uncomplexed quinolones [11,12,13,14] From these studies, ruthenium, gold, and silver have shown to be interesting molecules for cancer and antiviral therapies [15,16,17]. Cervical cancer treatment generally overrides the drugs used; new compounds with cell proliferation inhibition potential are imperative. Synthesis of fluoroquinolone with new modifications represents an opportunity to find new compounds that could be used in cancer treatment
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