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Article

The Effect of Conjugation of Ciprofloxacin and Moxifloxacin with Fatty Acids on Their Antibacterial and Anticancer Activity

1
Chair and Department of Biochemistry, Medical University of Warsaw, Ul. Banacha 1, 02-097 Warsaw, Poland
2
Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland
3
Bioinformatics Laboratory, Mossakowski Medical Research Institute, Polish Academy of Sciences, 5 Pawinskiego St., 02-106 Warsaw, Poland
4
Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, 02-089 Warsaw, Poland
5
Department of Microbiology, National Tuberculosis and Lung Diseases Research Institute, 01-138 Warsaw, Poland
6
Centre for Preclinical Research, Department of Pharmaceutical Microbiology, Medical University of Warsaw, 02-097 Warszawa, Poland
7
Department of Biochemistry and Pharmacogenomics, Faculty of Pharmacy, Medical University of Warsaw, 02-097 Warsaw, Poland
*
Authors to whom correspondence should be addressed.
Academic Editor: Robert Bucki
Int. J. Mol. Sci. 2022, 23(11), 6261; https://doi.org/10.3390/ijms23116261
Received: 6 May 2022 / Revised: 18 May 2022 / Accepted: 30 May 2022 / Published: 2 June 2022
(This article belongs to the Special Issue New Antibacterial Agents)
Novel conjugates (CP) of moxifloxacin (MXF) with fatty acids (1m16m) were synthesized with good yields utilizing amides chemistry. They exhibit a more pronounced cytotoxic potential than the parent drug. They were the most effective for prostate cancer cells with an IC50 below 5 µM for respective conjugates with sorbic (2m), oleic (4m), 6-heptenoic (10m), linoleic (11m), caprylic (15m), and stearic (16m) acids. All derivatives were evaluated against a panel of standard and clinical bacterial strains, as well as towards mycobacteria. The highest activity towards standard isolates was observed for the acetic acid derivative 14m, followed by conjugates of unsaturated crotonic (1m) and sorbic (2m) acids. The activity of conjugates tested against an expanded panel of clinical coagulase-negative staphylococci showed that the compound (14m) was recognized as a leading structure with an MIC of 0.5 μg/mL denoted for all quinolone-susceptible isolates. In the group of CP derivatives, sorbic (2) and geranic (3) acid amides exhibited the highest bactericidal potential against clinical strains. The M. tuberculosis Spec. 210 strain was the most sensitive to sorbic (2m) conjugate and to conjugates with medium- and long-chain polyunsaturated acids. To establish the mechanism of antibacterial action, selected CP and MXF conjugates were examined in both topoisomerase IV decatenation assay and the DNA gyrase supercoiling assay, followed by suitable molecular docking studies. View Full-Text
Keywords: fluoroquinolone; conjugation; fatty acids; cytotoxicity; antibacterial activity fluoroquinolone; conjugation; fatty acids; cytotoxicity; antibacterial activity
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MDPI and ACS Style

Chrzanowska, A.; Struga, M.; Roszkowski, P.; Koliński, M.; Kmiecik, S.; Jałbrzykowska, K.; Zabost, A.; Stefańska, J.; Augustynowicz-Kopeć, E.; Wrzosek, M.; Bielenica, A. The Effect of Conjugation of Ciprofloxacin and Moxifloxacin with Fatty Acids on Their Antibacterial and Anticancer Activity. Int. J. Mol. Sci. 2022, 23, 6261. https://doi.org/10.3390/ijms23116261

AMA Style

Chrzanowska A, Struga M, Roszkowski P, Koliński M, Kmiecik S, Jałbrzykowska K, Zabost A, Stefańska J, Augustynowicz-Kopeć E, Wrzosek M, Bielenica A. The Effect of Conjugation of Ciprofloxacin and Moxifloxacin with Fatty Acids on Their Antibacterial and Anticancer Activity. International Journal of Molecular Sciences. 2022; 23(11):6261. https://doi.org/10.3390/ijms23116261

Chicago/Turabian Style

Chrzanowska, Alicja, Marta Struga, Piotr Roszkowski, Michał Koliński, Sebastian Kmiecik, Karolina Jałbrzykowska, Anna Zabost, Joanna Stefańska, Ewa Augustynowicz-Kopeć, Małgorzata Wrzosek, and Anna Bielenica. 2022. "The Effect of Conjugation of Ciprofloxacin and Moxifloxacin with Fatty Acids on Their Antibacterial and Anticancer Activity" International Journal of Molecular Sciences 23, no. 11: 6261. https://doi.org/10.3390/ijms23116261

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