Ciprofloxacin conjugated to diphenyltin(iv): a novel formulation with enhanced antimicrobial activity
Date
2020-09-07Author
Chrysouli, M. P.Banti, Christina N.
Kourkoumelis, N.
Moushi, Eleni E.
Tasiopoulos, Anastasios J.
Douvalis, A.
Papachristodoulou, C.
Hatzidimitriou, Antonios G.
Bakas, T.
Hadjikakou, Sotiris K.
ISSN
1477-9226Publisher
Royal Society of ChemistryPlace of publication
Cambridge, UKSource
Dalton transactionsVolume
49Issue
33Pages
11522-11535Google Scholar check
Keyword(s):
Metadata
Show full item recordAbstract
The metalloantibiotic of formula Ph2Sn(CIP)2 (CIPTIN) (HCIP = ciprofloxacin) was synthesized by reacting ciprofloxacin hydrochloride (HCIP·HCl) (an antibiotic in clinical use) with diphenyltin dichloride (Ph2SnCl2DPTD). The complex was characterized in the solid state by melting point, FT-IR, X-ray Powder Diffraction (XRPD) analysis, 119Sn Mössbauer spectroscopy, X-ray Fluorescence (XRF) spectroscopy, and Thermogravimetry/Differential Thermal Analysis (TG-DTA) and in solution by UV-Vis, 1H NMR spectroscopic techniques and Electrospray Ionisation Mass Spectrometry (ESI-MS). The crystal structure of CIPTIN and its processor HCIP was also determined by X-ray crystallography. The antibacterial activity of CIPTIN, HCIP·HCl, HCIP and DPTD was evaluated against the bacterial species Pseudomonas aeruginosa (P. aeruginosa), Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and Staphylococcus epidermidis (S. epidermidis), by the means of Minimum Inhibitory Concentration (MIC), Minimum Bactericidal Concentration (MBC) and Inhibition Zones (IZs). CIPTIN shows lower MIC values than those of HCIP·HCl (up to 4.2-fold), HCIP (up to 2.7-fold) or DPTD (>135-fold), towards the tested microbes. CIPTIN is classified into bactericidal agents according to MBC/MIC values. The developing IZs are 40.8 ± 1.5, 34.0 ± 0.8, 36.0 ± 1.1 and 42.7 ± 0.8 mm, respectively which classify the microbes P. aeruginosa, E. coli, S. aureus and S. epidermidis to susceptible ones to CIPTIN. These IZs are greater than the corresponding ones of HCIP·HCl by 1.1 to 1.5-fold against both the tested Gram negative and Gram positive bacteria. CIPTIN eradicates the biofilm of P. aeruginosa and S. aureus more efficiently than HCIP·HCl and HCIP. The in vitro toxicity and genotoxicity of CIPTIN were tested against human skin keratinocyte cells (HaCaT) (IC50 = 2.33 μM). CIPTIN exhibits 2 to 9-fold lower MIC values than its IC50 against HaCaT, while its genotoxic effect determined by micronucleus assay is equivalent to the corresponding ones of HCIP·HCl or HCIP.
Collections
Cite as
Related items
Showing items related by title, author, creator and subject.
-
Article
Analysis of volatile organic compounds released from the decay of surrogate human models simulating victims of collapsed buildings by thermal desorption-comprehensive two-dimensional gas chromatography-time of flight mass spectrometry
Agapiou, Agapios; Zorba, Eleni; Mikedi, Katerina; McGregor, L.; Spiliopoulou, C.; Statheropoulos, Miltiades K. (2015)Field experiments were devised to mimic the entrapment conditions under the rubble of collapsed buildings aiming to investigate the evolution of volatile organic compounds (VOCs) during the early dead body decomposition ...
-
Article
Detection of a photostable five-coordinate heme a3-Fe-Co species and functional implications of His384/α10 in CO-bound ba 3-cytochrome c oxidase from Thermus thermophilus
Ohta, T.; Pinakoulaki, Eftychia; Soulimane, T.; Kitagawa, T.; Varotsis, Constantinos (2004)Resonance Raman (RR) spectra are reported for the fully reduced carbon monoxy derivative of ba3-cytochrome c oxidase from Thermus thermophilus. The RR spectra show the formation of a photolabile six-coordinate heme-CO and ...
-
Article
Synthesis, structural characterization and in vitro inhibitory studies against human breast cancer of the bis-(2,6-di-tert-butylphenol)tin(iv) dichloride and its complexes
Shpakovsky, D. B.; Banti, Christina N.; Beaulieu-Houle, G.; Kourkoumelis, Nikolaos; Manoli, Maria; Manos, Manolis J.; Tasiopoulos, Anastasios J.; Hadjikakou, Sotiris K.; Milaeva, E. R.; Charalabopoulos, Konstantinos A.; Bakas, Thomas V.; Butler, I. S.; Hadjiliadis, Nick (2012)Four new organotin(iv) complexes of bis-(2,6-di-tert-butylphenol)tin(iv) dichloride [(tert-Bu-)2(HO-Ph)]2SnCl2 (1) with the heterocyclic thioamides 2-mercapto-pyrimidine (PMTH), 2-mercapto-4-methyl- pyrimidine (MPMTH), ...