Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme
2016
Autori
Vilipić, Jovana P.Novaković, Irena
Zlatović, Mario
Vujčić, Miroslava
Tufegdžić, Srđan
Sladić, Dušan
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. Sodium dodecyl sulphate (SDS) gel electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e., the existence of interactions between the quinones and calf thymus DNA (CT-DNA). Determination of the binding constants by absorption titration indicated weak interactions between the quinone derivatives and CT-DNA. The quenching of fluorescence of the intercalator ethidium bromide (EB) from the EB-CT-DNA system and of the minor groove binder Hoechst 33258 (H) from the H-CT-DNA system by the synthesized derivatives indicated interactions of the compounds and CT-DNA. Circular dichroism (CD) spectra demonstrated a non-intercalative binding mode of the quinone derivatives to CT-DNA. Molecular docking results confirmed binding to the minor groove. The electrophoretic p...attern showed no cleavage of the pUC19 plasmid in the presence of any of the synthesized compounds. The ability of the derivatives to scavenge radicals was confirmed by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. All the presented results suggest that the DNA minor groove binding is the principal mechanism of action of the examined amino acid derivatives.
Ključne reči:
quinone / DNA binding / minor groove / fluorescenceIzvor:
Journal of the Serbian Chemical Society, 2016, 81, 12, 1345-1358Izdavač:
- Serbian Chemical Soc, Belgrade
Finansiranje / projekti:
- Interakcije prirodnih proizvoda, njihovih derivata i kompleksnih jedinjenja sa proteinima i nukleinskim kiselinama (RS-MESTD-Basic Research (BR or ON)-172055)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
DOI: 10.2298/JSC160725101V
ISSN: 0352-5139
WoS: 000392946100002
Scopus: 2-s2.0-85009807714
Institucija/grupa
IHTMTY - JOUR AU - Vilipić, Jovana P. AU - Novaković, Irena AU - Zlatović, Mario AU - Vujčić, Miroslava AU - Tufegdžić, Srđan AU - Sladić, Dušan PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2049 AB - The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. Sodium dodecyl sulphate (SDS) gel electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e., the existence of interactions between the quinones and calf thymus DNA (CT-DNA). Determination of the binding constants by absorption titration indicated weak interactions between the quinone derivatives and CT-DNA. The quenching of fluorescence of the intercalator ethidium bromide (EB) from the EB-CT-DNA system and of the minor groove binder Hoechst 33258 (H) from the H-CT-DNA system by the synthesized derivatives indicated interactions of the compounds and CT-DNA. Circular dichroism (CD) spectra demonstrated a non-intercalative binding mode of the quinone derivatives to CT-DNA. Molecular docking results confirmed binding to the minor groove. The electrophoretic pattern showed no cleavage of the pUC19 plasmid in the presence of any of the synthesized compounds. The ability of the derivatives to scavenge radicals was confirmed by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. All the presented results suggest that the DNA minor groove binding is the principal mechanism of action of the examined amino acid derivatives. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme VL - 81 IS - 12 SP - 1345 EP - 1358 DO - 10.2298/JSC160725101V ER -
@article{ author = "Vilipić, Jovana P. and Novaković, Irena and Zlatović, Mario and Vujčić, Miroslava and Tufegdžić, Srđan and Sladić, Dušan", year = "2016", abstract = "The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. Sodium dodecyl sulphate (SDS) gel electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e., the existence of interactions between the quinones and calf thymus DNA (CT-DNA). Determination of the binding constants by absorption titration indicated weak interactions between the quinone derivatives and CT-DNA. The quenching of fluorescence of the intercalator ethidium bromide (EB) from the EB-CT-DNA system and of the minor groove binder Hoechst 33258 (H) from the H-CT-DNA system by the synthesized derivatives indicated interactions of the compounds and CT-DNA. Circular dichroism (CD) spectra demonstrated a non-intercalative binding mode of the quinone derivatives to CT-DNA. Molecular docking results confirmed binding to the minor groove. The electrophoretic pattern showed no cleavage of the pUC19 plasmid in the presence of any of the synthesized compounds. The ability of the derivatives to scavenge radicals was confirmed by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. All the presented results suggest that the DNA minor groove binding is the principal mechanism of action of the examined amino acid derivatives.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme", volume = "81", number = "12", pages = "1345-1358", doi = "10.2298/JSC160725101V" }
Vilipić, J. P., Novaković, I., Zlatović, M., Vujčić, M., Tufegdžić, S.,& Sladić, D.. (2016). Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 81(12), 1345-1358. https://doi.org/10.2298/JSC160725101V
Vilipić JP, Novaković I, Zlatović M, Vujčić M, Tufegdžić S, Sladić D. Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme. in Journal of the Serbian Chemical Society. 2016;81(12):1345-1358. doi:10.2298/JSC160725101V .
Vilipić, Jovana P., Novaković, Irena, Zlatović, Mario, Vujčić, Miroslava, Tufegdžić, Srđan, Sladić, Dušan, "Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme" in Journal of the Serbian Chemical Society, 81, no. 12 (2016):1345-1358, https://doi.org/10.2298/JSC160725101V . .