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Synthesis and biological activity of quaternary salts of 3-N-dodecylaminoquinuclidine


Odžak, Renata; Šprung, Matilda; Soldo, Barbara; Maravić, Ana; Bazina, Linda; Radman Kastelić, Andreja; Hrenar, Tomica; Primožič, Ines
Synthesis and biological activity of quaternary salts of 3-N-dodecylaminoquinuclidine // Book of abstracts JMMC 2019 –Joint Meeting on Medicinal Chemistry 2019
Prag: GUARANT International spol. s r.o., 2019. str. 100-100 (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Synthesis and biological activity of quaternary salts of 3-N-dodecylaminoquinuclidine

Autori
Odžak, Renata ; Šprung, Matilda ; Soldo, Barbara ; Maravić, Ana ; Bazina, Linda ; Radman Kastelić, Andreja ; Hrenar, Tomica ; Primožič, Ines

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of abstracts JMMC 2019 –Joint Meeting on Medicinal Chemistry 2019 / - Prag : GUARANT International spol. s r.o., 2019, 100-100

ISBN
978-80-907442-0-2

Skup
Joint Meeting on Medicinal Chemistry 2019

Mjesto i datum
Prag, Češka, 27-30.06.2019.

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Quaternary salts, quinuclidine-3-yl(dodec-1-yl)amine, antimicrobial activity, cytotoxicity

Sažetak
In an attempt to identify a new class of antimicrobial agents, the antimicrobial potential of quaternary quinuclidinium derivativeswith N-alkyl substituent on the position 3 of quinuclidine was evaluated.We were guided bythe results of our previouswork which showedthatquaternary derivatives of 3-substituted quinuclidineshavevery good biological activity.1Therefore, newseriesof quaternary quinuclidiniumsalts were designed and synthetized by the quaternization of quinuclidin-3-yl(dodec-1-yl)aminewith different benzyl bromides. All compounds were obtained in very good yields after which they were further characterized by physico-chemical methods includingFTIR, 1H and 13C NMR spectroscopies.The antibacterial activities of all compounds were evaluated against series of recent clinical isolates of antibiotic susceptible Gram-positive and resistant Gram-negative pathogens by determining their minimum inhibitory concentrations. All compounds showed good to strong broad-spectrum activity displaying MIC values between1.95-3.9 μg/mL.Cytotoxicity of compounds with different cell lines in human cell culture was determinedand it was determined that HaCat cell line is less tolerant that RPE1 displaying IC50values between 0.97-24.3 μM/mL. Based on these results, quaternary quinuclidine with long alkyl chain can be considered as promising new class of antimicrobials and further investigations should be performed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
IP-2016-06-3775 ADESIRE

Ustanove
Prirodoslovno-matematički fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Split