In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives

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dc.contributor.authorDumitrascu, Florea
dc.contributor.authorUdrea, Ana-Maria
dc.contributor.authorCaira, Mino R.
dc.contributor.authorNuta, Diana Camelia
dc.contributor.authorLimban, Carmen
dc.contributor.authorChifiriuc, Mariana Carmen
dc.contributor.authorPopa, Marcela
dc.contributor.authorBleotu, Coralia
dc.contributor.authorHanganu, Anamaria
dc.contributor.authorDumitrescu, Denisa
dc.contributor.authorAvram, Speranta
dc.date.accessioned2022-07-08T07:24:45Z
dc.date.available2022-07-08T07:24:45Z
dc.date.issued2022-04-23
dc.date.updated2022-05-12T19:36:00Z
dc.description.abstractThe efficient regioselective bromination and iodination of the nonsteroidal anti-inflammatory drug (NSAID) carprofen were achieved by using bromine and iodine monochloride in glacial acetic acid. The novel halogenated carprofen derivatives were functionalized at the carboxylic group by esterification. The regioselectivity of the halogenation reaction was evidenced by NMR spectroscopy and confirmed by X-ray analysis. The compounds were screened for their in vitro antibacterial activity against planktonic cells and also for their anti-biofilm effect, using Gram-positive bacteria (<i>Staphylococcus aureus</i> ATCC 29213, <i>Enterococcus faecalis</i> ATCC 29212) and Gram-negative bacteria (<i>Escherichia coli</i> ATCC 25922 and <i>Pseudomonas aeruginosa</i> ATCC 27853). The cytotoxic activity of the novel compounds was tested against HeLa cells. The pharmacokinetic and pharmacodynamic profiles of carprofen derivatives, as well as their toxicity, were established by in silico analyses.
dc.identifierdoi: 10.3390/molecules27092722
dc.identifier.apacitationDumitrascu, F., Udrea, A., Caira, Mino R., Nuta, D. C., Limban, C., Chifiriuc, M. C., ... Avram, S. (2022). In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives. <i>Molecules</i>, 27(9), http://hdl.handle.net/11427/36632en_ZA
dc.identifier.chicagocitationDumitrascu, Florea, Ana-Maria Udrea, Mino R. Caira, Diana Camelia Nuta, Carmen Limban, Mariana Carmen Chifiriuc, Marcela Popa, et al "In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives." <i>Molecules</i> 27, 9. (2022) http://hdl.handle.net/11427/36632en_ZA
dc.identifier.citationDumitrascu, F., Udrea, A., Caira, Mino R., Nuta, D.C., Limban, C., Chifiriuc, M.C., Popa, M. & Bleotu, C. et al. 2022. In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives. <i>Molecules.</i> 27(9) http://hdl.handle.net/11427/36632en_ZA
dc.identifier.ris TY - Journal Article AU - Dumitrascu, Florea AU - Udrea, Ana-Maria AU - Caira, Mino R. AU - Nuta, Diana Camelia AU - Limban, Carmen AU - Chifiriuc, Mariana Carmen AU - Popa, Marcela AU - Bleotu, Coralia AU - Hanganu, Anamaria AU - Dumitrescu, Denisa AU - Avram, Speranta AB - The efficient regioselective bromination and iodination of the nonsteroidal anti-inflammatory drug (NSAID) carprofen were achieved by using bromine and iodine monochloride in glacial acetic acid. The novel halogenated carprofen derivatives were functionalized at the carboxylic group by esterification. The regioselectivity of the halogenation reaction was evidenced by NMR spectroscopy and confirmed by X-ray analysis. The compounds were screened for their in vitro antibacterial activity against planktonic cells and also for their anti-biofilm effect, using Gram-positive bacteria (<i>Staphylococcus aureus</i> ATCC 29213, <i>Enterococcus faecalis</i> ATCC 29212) and Gram-negative bacteria (<i>Escherichia coli</i> ATCC 25922 and <i>Pseudomonas aeruginosa</i> ATCC 27853). The cytotoxic activity of the novel compounds was tested against HeLa cells. The pharmacokinetic and pharmacodynamic profiles of carprofen derivatives, as well as their toxicity, were established by in silico analyses. DA - 2022-04-23 DB - OpenUCT DP - University of Cape Town IS - 9 J1 - Molecules KW - carprofen KW - halogenation KW - antimicrobial activity KW - 3-bromocarprofen KW - 3-iodocarprofen KW - iodine monochloride KW - carbazole KW - halogen bonding LK - https://open.uct.ac.za PY - 2022 T1 - In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives TI - In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives UR - http://hdl.handle.net/11427/36632 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/36632
dc.identifier.urihttps://doi.org/10.3390/molecules27092722
dc.identifier.vancouvercitationDumitrascu F, Udrea A, Caira Mino R, Nuta DC, Limban C, Chifiriuc MC, et al. In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives. Molecules. 2022;27(9) http://hdl.handle.net/11427/36632.en_ZA
dc.publisherMultidisciplinary Digital Publishing Institute
dc.rights.licensehttps://creativecommons.org/licenses/by/4.0/
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceMolecules
dc.source.journalissue9
dc.source.journalvolume27
dc.subjectcarprofen
dc.subjecthalogenation
dc.subjectantimicrobial activity
dc.subject3-bromocarprofen
dc.subject3-iodocarprofen
dc.subjectiodine monochloride
dc.subjectcarbazole
dc.subjecthalogen bonding
dc.titleIn Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives
dc.typeJournal Article
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