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Design and Synthesis of Menthol and Thymol Derived Ciprofloxacin: Influence of Structural Modifications on the Antibacterial Activity and Anticancer Properties

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dc.abstract.enSixteen new Ciprofloxacin derivatives were designed and successfully synthesized. In an in silico experiment, lipophilicity was established for obtained compounds. All compounds were screened for antimicrobial activity using standard and clinical strains. As for Gram-positive hospital microorganisms, all tested derivatives were active. Measured MICs were in the range 1–16 µg/mL, confirming high antimicrobial potency. Derivative 12 demonstrated activity against all standard Gram-positive Staphylococci, within the range of 0.8–1.6 µg/mL and was confirmed as the leading structure with MICs 1 µg/mL for S. pasteuri KR 4358 and S. aureus T 5591 (clinical strains). All compounds were screened for their in vitro cytotoxic properties via the MTT method. Three of the examined compounds (3, 11 and 16) showed good activity against cancer cells, and in parallel were found not to be cytotoxic toward normal cells. Doxorubicin SI ranged 0.14–1.11 while the mentioned three ranged 1.9–3.4. Selected Ciprofloxacin derivatives were docked into the crystal structure of topoisomerase II (DNA gyrase) in complex with DNA (PDB ID: 5BTC). In summary, leading structures were established (3, 11, 12 and 16). We have observed poor results in preformed studies for disubstituted derivatives, suggesting that 3-oxo-4-carboxylic acid core is the active DNA-gyrase binding site, and when structural changes were made in this fragment, there was an observed decrease in antibacterial potency.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorRoszkowski, Piotr
dc.contributor.authorStruga, Marta
dc.contributor.authorChaniewicz, Kinga
dc.contributor.authorRajkowska, Eliza
dc.contributor.authorZawodnik, Aleksandra
dc.contributor.authorOtto-Ślusarczyk, Dagmara
dc.contributor.authorKmiecik, Sebastian
dc.contributor.authorKoliński, Michał
dc.contributor.authorSzymańska-Majchrzak, Jolanta
dc.contributor.authorSzulczyk, Daniel
dc.contributor.authorSzostek, Tomasz
dc.date.accessioned2024-01-24T21:33:25Z
dc.date.available2024-01-24T21:33:25Z
dc.date.copyright2022-06-13
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number12
dc.description.versionFINAL_PUBLISHED
dc.description.volume23
dc.identifier.doi10.3390/IJMS23126600
dc.identifier.issn1422-0067
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/104599
dc.identifier.weblinkhttps://www.mdpi.com/1422-0067/23/12/6600/pdf
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofInternational Journal of Molecular Sciences
dc.relation.pages6600
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enantimicrobial
dc.subject.enCiprofloxacin
dc.subject.enantibiotic
dc.subject.enthymol
dc.subject.enmenthol
dc.titleDesign and Synthesis of Menthol and Thymol Derived Ciprofloxacin: Influence of Structural Modifications on the Antibacterial Activity and Anticancer Properties
dc.typeJournalArticle
dspace.entity.typePublication