Antiproliferative and antibacterial activity of some glutarimide derivatives
Abstract
Antiproliferative and antibacterial activities of nine glutarimide derivatives (1–9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11]heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9–27 μM). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6–8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl)butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 × 10−3 mol/L). Distinction between more and... less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.
Keywords:
Antitumor agents / heterocycles / structure–activity analysisSource:
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, 31, 915-923Publisher:
- Taylor and Francis Ltd
Funding / projects:
- Structure-activity relationship of newly synthesized biological active compound (RS-MESTD-Basic Research (BR or ON)-172032)
- Biological response modifiers in physiological and pathological conditions (RS-MESTD-Basic Research (BR or ON)-175011)
DOI: 10.3109/14756366.2015.1070844
ISSN: 1475-6366
PubMed: 26247353
WoS: 000385270300008
Scopus: 2-s2.0-84939214288
Collections
Institution/Community
IHTMTY - JOUR AU - Popović-Đorđević, Jelena B. AU - Klaus, Anita AU - Žižak, Željko AU - Matić, Ivana Z. AU - Drakulić, Branko PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2667 AB - Antiproliferative and antibacterial activities of nine glutarimide derivatives (1–9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11]heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9–27 μM). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6–8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl)butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 × 10−3 mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields. PB - Taylor and Francis Ltd T2 - Journal of Enzyme Inhibition and Medicinal Chemistry T1 - Antiproliferative and antibacterial activity of some glutarimide derivatives VL - 31 SP - 915 EP - 923 DO - 10.3109/14756366.2015.1070844 ER -
@article{ author = "Popović-Đorđević, Jelena B. and Klaus, Anita and Žižak, Željko and Matić, Ivana Z. and Drakulić, Branko", year = "2016", abstract = "Antiproliferative and antibacterial activities of nine glutarimide derivatives (1–9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11]heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9–27 μM). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6–8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl)butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 × 10−3 mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.", publisher = "Taylor and Francis Ltd", journal = "Journal of Enzyme Inhibition and Medicinal Chemistry", title = "Antiproliferative and antibacterial activity of some glutarimide derivatives", volume = "31", pages = "915-923", doi = "10.3109/14756366.2015.1070844" }
Popović-Đorđević, J. B., Klaus, A., Žižak, Ž., Matić, I. Z.,& Drakulić, B.. (2016). Antiproliferative and antibacterial activity of some glutarimide derivatives. in Journal of Enzyme Inhibition and Medicinal Chemistry Taylor and Francis Ltd., 31, 915-923. https://doi.org/10.3109/14756366.2015.1070844
Popović-Đorđević JB, Klaus A, Žižak Ž, Matić IZ, Drakulić B. Antiproliferative and antibacterial activity of some glutarimide derivatives. in Journal of Enzyme Inhibition and Medicinal Chemistry. 2016;31:915-923. doi:10.3109/14756366.2015.1070844 .
Popović-Đorđević, Jelena B., Klaus, Anita, Žižak, Željko, Matić, Ivana Z., Drakulić, Branko, "Antiproliferative and antibacterial activity of some glutarimide derivatives" in Journal of Enzyme Inhibition and Medicinal Chemistry, 31 (2016):915-923, https://doi.org/10.3109/14756366.2015.1070844 . .