PMID- 37834266 OWN - NLM STAT- MEDLINE DCOM- 20231023 LR - 20231023 IS - 1422-0067 (Electronic) IS - 1422-0067 (Linking) VI - 24 IP - 19 DP - 2023 Oct 1 TI - Synthesis, Physicochemical Characterization using a Facile Validated HPLC Quantitation Analysis Method of 4-Chloro-phenylcarbamoyl-methyl Ciprofloxacin and Its Biological Investigations. LID - 10.3390/ijms241914818 [doi] LID - 14818 AB - 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, (1)H NMR, (13)C 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 microg/mL, respectively, in contrast to Cpx, which had IC50 values of 2.125 and 0.821 microg/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. FAU - Al-Hakkani, Mostafa F AU - Al-Hakkani MF AUID- ORCID: 0000-0003-0004-8939 AD - Department of Research, Development, and Stability, UP Pharma, Industrial Zone, Arab El Awamer, Abnoub 76, Assiut 71745, Egypt. FAU - Ahmed, Nourhan AU - Ahmed N AD - Department of Research, Development, and Stability, UP Pharma, Industrial Zone, Arab El Awamer, Abnoub 76, Assiut 71745, Egypt. FAU - Abbas, Alaa A AU - Abbas AA AD - Department of Research, Development, and Stability, UP Pharma, Industrial Zone, Arab El Awamer, Abnoub 76, Assiut 71745, Egypt. FAU - Hassan, Mohammad H A AU - Hassan MHA AD - Department of Medical Laboratory Technology, Higher Technological Institute for Applied Health Sciences in Minya, Minya 71511, Egypt. FAU - Aziz, Hossameldin A AU - Aziz HA AD - Department of Pharmaceutical Chemistry, Faculty of Pharmacy, New Valley University, New Valley 72511, Egypt. FAU - Elshamsy, Ali M AU - Elshamsy AM AD - Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Deraya University, Mina, New Minia 61768, Egypt. FAU - Khalifa, Hazim O AU - Khalifa HO AUID- ORCID: 0000-0001-9861-9693 AD - Department of Veterinary Medicine, College of Agriculture and Veterinary Medicine, United Arab Emirates University, Al Ain P.O. Box 1555, United Arab Emirates. AD - Department of Pharmacology, Faculty of Veterinary Medicine, Kafr Elsheikh University, Kafr El Sheikh 33516, Egypt. FAU - Abdelshakour, Mohamed A AU - Abdelshakour MA AD - Department of Pharmaceutical Analytical Chemistry, Faculty of Pharmacy, Sohag University, Sohag 82524, Egypt. FAU - Saddik, Mohammed S AU - Saddik MS AUID- ORCID: 0000-0001-5236-7419 AD - Department of Pharmaceutics and Clinical Pharmacy, Faculty of Pharmacy, Sohag University, Sohag 82524, Egypt. FAU - Elsayed, Mahmoud M A AU - Elsayed MMA AUID- ORCID: 0000-0001-9547-2243 AD - Department of Pharmaceutics and Clinical Pharmacy, Faculty of Pharmacy, Sohag University, Sohag 82524, Egypt. FAU - Sabet, Marwa A AU - Sabet MA AUID- ORCID: 0000-0001-9557-1153 AD - Department of Microbiology and Immunology, Faculty of Pharmacy, Sphinx University, New-Assiut 71684, Egypt. FAU - El-Mokhtar, Mohamed A AU - El-Mokhtar MA AUID- ORCID: 0000-0003-1943-8419 AD - Department of Medical Microbiology and Immunology, Faculty of Medicine, Assiut University, Assiut 71515, Egypt. FAU - Alsehli, Mosa AU - Alsehli M AD - Department of Chemistry, College of Science, Taibah University, Madinah P.O. Box 344, Saudi Arabia. FAU - Amin, M S AU - Amin MS AD - Department of Chemistry, College of Science, Taibah University, Madinah P.O. Box 344, Saudi Arabia. AD - Chemistry Department, Faculty of science, Ain Shams University, Cairo 11566, Egypt. FAU - Abu-Dief, Ahmed M AU - Abu-Dief AM AD - Department of Chemistry, College of Science, Taibah University, Madinah P.O. Box 344, Saudi Arabia. AD - Department of Chemistry, Faculty of Science, Sohag University, Sohag 82524, Egypt. FAU - Mohammed, Hamada H H AU - Mohammed HHH AUID- ORCID: 0000-0002-8649-7534 AD - Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Sohag University, Sohag 82524, Egypt. LA - eng GR - 445-9-333/Taibah University/ PT - Journal Article DEP - 20231001 PL - Switzerland TA - Int J Mol Sci JT - International journal of molecular sciences JID - 101092791 RN - 5E8K9I0O4U (Ciprofloxacin) RN - 0 (Anti-Bacterial Agents) RN - EC 5.99.1.3 (DNA Gyrase) RN - 0 (Topoisomerase II Inhibitors) SB - IM MH - *Ciprofloxacin/pharmacology/chemistry MH - *Staphylococcus aureus MH - Chromatography, High Pressure Liquid MH - Spectroscopy, Fourier Transform Infrared MH - Microbial Sensitivity Tests MH - Anti-Bacterial Agents/chemistry MH - DNA Gyrase MH - Molecular Docking Simulation MH - Topoisomerase II Inhibitors/pharmacology/chemistry PMC - PMC10573198 OTO - NOTNLM OT - DNA gyrase OT - HPLC OT - antibacterial OT - anticancer OT - ciprofloxacin OT - docking studies OT - validation COIS- The authors declare no conflict of interest. EDAT- 2023/10/14 10:47 MHDA- 2023/10/23 01:18 PMCR- 2023/10/01 CRDT- 2023/10/14 01:03 PHST- 2023/09/08 00:00 [received] PHST- 2023/09/26 00:00 [revised] PHST- 2023/09/30 00:00 [accepted] PHST- 2023/10/23 01:18 [medline] PHST- 2023/10/14 10:47 [pubmed] PHST- 2023/10/14 01:03 [entrez] PHST- 2023/10/01 00:00 [pmc-release] AID - ijms241914818 [pii] AID - ijms-24-14818 [pii] AID - 10.3390/ijms241914818 [doi] PST - epublish SO - Int J Mol Sci. 2023 Oct 1;24(19):14818. doi: 10.3390/ijms241914818.