Synthesis, Physicochemical Characterization using a Facile Validated HPLC Quantitation Analysis Method of 4-Chloro-phenylcarbamoyl-methyl Ciprofloxacin and Its Biological Investigations

• Published in: International journal of molecular sciences Vol. 24; no. 19; p. 14818
• Main Authors: Al-Hakkani, Mostafa F., Ahmed, Nourhan, Abbas, Alaa A., Hassan, Mohammad H. A., Aziz, Hossameldin A., Elshamsy, Ali M., Khalifa, Hazim O., Abdelshakour, Mohamed A., Saddik, Mohammed S., Elsayed, Mahmoud M. A., Sabet, Marwa A., El-Mokhtar, Mohamed A., Alsehli, Mosa, Amin, M. S., Abu-Dief, Ahmed M., Mohammed, Hamada H. H.
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 01.10.2023; MDPI
• Subjects: Antibiotics; Cancer; Ciprofloxacin; Drug resistance; Enzymes; Gram-positive bacteria; High performance liquid chromatography; Investigations; Methods; Particle size; Pharmaceutical industry; Spectrum analysis; Staphylococcus aureus; Egypt
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms241914818

A novel derivative of ciprofloxacin (Cpx) was synthesized and characterized using various analytical techniques, including FT-IR spectroscopy, UV-Vis spectroscopy, TEM and SEM analysis, 1H NMR, 13C NMR, and HPLC analysis. The newly prepared Cpx derivative (Cpx-Drv) exhibited significantly enhanced antibacterial properties compared to Cpx itself. In particular, Cpx-Drv demonstrated a 51% increase in antibacterial activity against S. aureus and a 30% improvement against B. subtilis. It displayed potent inhibitory effects on topoisomerases II (DNA gyrase and topoisomerase IV) as potential molecular targets, with IC50 values of 6.754 and 1.913 µg/mL, respectively, in contrast to Cpx, which had IC50 values of 2.125 and 0.821 µg/mL, respectively. Docking studies further supported these findings, showing that Cpx-Drv exhibited stronger binding interactions with the gyrase enzyme (PDB ID: 2XCT) compared to the parent Cpx, with binding affinities of −10.3349 and −7.7506 kcal/mole, respectively.