KFU. Card publication. Novel Fluoroquinolones With Pinane Moiety: Synthesis and Antimicrobial Activity

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NOVEL FLUOROQUINOLONES WITH PINANE MOIETY: SYNTHESIS AND ANTIMICROBIAL ACTIVITY

Form of presentation

Articles in international journals and collections

Year of publication

2025

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Authors, employees of KFU

Gilfanov Ilmir Rafisovich, author

Davletshin Rustam Rifkhatovich, author

Kayumov Ayrat Rashitovich, author

Klochkov Vladimir Vasilevich, author

Kolesnikova Alyona Igorevna, author

Lisovskaya Svetlana Anatolevna, author

Nikitina Liliya Evgenevna, author

Pavelev Roman Sergeevich, author

Rakhmatullin Ilfat Zufarovich, author

Trizna Elena Yurevna, author

Bibliographic description in the original language

Gilfanov I.R. Novel Fluoroquinolones With Pinane Moiety: Synthesis and Antimicrobial Activity / I.R. Gilfanov, A.I. Kolesnikova, R.S. Pavelyev, D.V. Sudarikov, P.V. Gribkov, E.S. Izmest'ev, S.A. Rubtsova, S.A. Lisovskaya, O.B. Babaeva, I.Z. Rakhmatullin, R.R. Davletshin, V.V. Klochkov, L.E. Nikitina, A.R. Kayumov, E.Y. Trizna // Chemistry & Biodiversity - 2025. - 0:e202402601. https://doi.org/10.1002/cbdv.202402601

Annotation

Here, we report a synthesis of fluoroquinolones carrying a monoterpene moiety at the C7 position of aromatic structure. The minimal inhibitory concentrations of fluoroquinolone fused with trans-3-hydroxy-cis-myrtanylamine 18 against Staphylococcus aureus (MSSA isolates) were two- to eightfold lower compared to moxifloxacin, although fourfold higher against MRSA isolates. The fluoroquinolone fused with (−)-nopylamine 16 was four- to eightfold less active on MSSA compared to moxifloxacin, while had similar activity on MRSA. Against biofilms, both 16 and 18 were four times more active than both moxifloxacin and ciprofloxacin. Both 16 and 18 induced the drop of membrane potential and in silico exhibited similar binding energies with DNA gyrase of S. aureus (ΔG −13.44 to −13.17 kcal/mol), suggesting dual mechanism of action (topoisomerase inhibition by the fluoroquinolone core and membrane damage by the monoterpene fragment). Thus, our data demonstrate the perspectives of monoterpenes fusion to an antibiotic moiety to obtain dual-acting bipharmacophore antimicrobials with improved activity, including biofilm-associated infections.

Keywords

antibacterial activity | antifungal activity | fluoroquinolones | molecular docking | pinane monoterpenoids

The name of the journal

Chemistry and Biodiversity

URL

https://onlinelibrary.wiley.com/doi/10.1002/cbdv.202402601

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=309422&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Gilfanov Ilmir Rafisovich	ru_RU
dc.contributor.author	Davletshin Rustam Rifkhatovich	ru_RU
dc.contributor.author	Kayumov Ayrat Rashitovich	ru_RU
dc.contributor.author	Klochkov Vladimir Vasilevich	ru_RU
dc.contributor.author	Kolesnikova Alyona Igorevna	ru_RU
dc.contributor.author	Lisovskaya Svetlana Anatolevna	ru_RU
dc.contributor.author	Nikitina Liliya Evgenevna	ru_RU
dc.contributor.author	Pavelev Roman Sergeevich	ru_RU
dc.contributor.author	Rakhmatullin Ilfat Zufarovich	ru_RU
dc.contributor.author	Trizna Elena Yurevna	ru_RU
dc.date.accessioned	2025-01-01T00:00:00Z	ru_RU
dc.date.available	2025-01-01T00:00:00Z	ru_RU
dc.date.issued	2025	ru_RU
dc.identifier.citation	Gilfanov I.R. Novel Fluoroquinolones With Pinane Moiety: Synthesis and Antimicrobial Activity / I.R. Gilfanov, A.I. Kolesnikova, R.S. Pavelyev, D.V. Sudarikov, P.V. Gribkov, E.S. Izmest'ev, S.A. Rubtsova, S.A. Lisovskaya, O.B. Babaeva, I.Z. Rakhmatullin, R.R. Davletshin, V.V. Klochkov, L.E. Nikitina, A.R. Kayumov, E.Y. Trizna // Chemistry & Biodiversity - 2025. - 0:e202402601. https://doi.org/10.1002/cbdv.202402601	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=309422&p_lang=2	ru_RU
dc.description.abstract	Chemistry and Biodiversity	ru_RU
dc.description.abstract	Here, we report a synthesis of fluoroquinolones carrying a monoterpene moiety at the C7 position of aromatic structure. The minimal inhibitory concentrations of fluoroquinolone fused with trans-3-hydroxy-cis-myrtanylamine 18 against Staphylococcus aureus (MSSA isolates) were two- to eightfold lower compared to moxifloxacin, although fourfold higher against MRSA isolates. The fluoroquinolone fused with (−)-nopylamine 16 was four- to eightfold less active on MSSA compared to moxifloxacin, while had similar activity on MRSA. Against biofilms, both 16 and 18 were four times more active than both moxifloxacin and ciprofloxacin. Both 16 and 18 induced the drop of membrane potential and in silico exhibited similar binding energies with DNA gyrase of S. aureus (ΔG −13.44 to −13.17 kcal/mol), suggesting dual mechanism of action (topoisomerase inhibition by the fluoroquinolone core and membrane damage by the monoterpene fragment). Thus, our data demonstrate the perspectives of monoterpenes fusion to an antibiotic moiety to obtain dual-acting bipharmacophore antimicrobials with improved activity, including biofilm-associated infections.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject		ru_RU
dc.title	Novel Fluoroquinolones With Pinane Moiety: Synthesis and Antimicrobial Activity	ru_RU
dc.type	Articles in international journals and collections	ru_RU