title: The study of naphthoquinones and their complexes with DNA by using Raman spectroscopy and surface enhanced Raman spectroscopy: new insight into interactions of DNA with plant secondary metabolites.
abstract: Naphthoquinones represent the group of plant secondary metabolites with cytotoxic properties based on their ability to generate reactive oxygen species and interfere with the processes of cell respiration. Due to this fact, the possible cytotoxic mechanisms on cellular and subcellular levels are investigated intensively. There are many targets of cytotoxic action on the cellular level; however, DNA is a critical target of many cytotoxic compounds. Due to the cytotoxic properties of naphthoquinones, it is necessary to study the processes of naphthoquinones, DNA interactions (1,4-naphthoquinone, binapthoquinone, juglone, lawsone, plumbagin), especially by using modern analytical techniques. In our work, the Raman spectroscopy was used to determine the possible binding sites of the naphthoquinones on the DNA and to characterize the bond of naphthoquinone to DNA. Experimental data reveals the relationships between the perturbations of structure-sensitive Raman bands and the types of the naphthoquinones involved. The modification of DNA by the studied naphthoquinones leads to the nonspecific interaction, which causes the transition of B-DNA into A-DNA conformation. The change of the B-conformation of DNA for all measured DNA modified by naphthoquinones except plumbagin is obvious.
authors.affiliation: Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1-3, 612 42 Brno, Czech Republic.
authors.forename: Veronika
authors.identifier: 0000-0002-3755-247X
authors.initials: V
authors.lastname: Vaverkova
authors.affiliation: Institute of Biophysics, Academy of Sciences of the Czech Republic, Kralovopolska 135, C612 65 Brno, Czech Republic.
authors.forename: Oldrich
authors.initials: O
authors.lastname: Vrana
authors.affiliation: Department of Chemistry and Biochemistry, Faculty of Agronomy, Mendel University in Brno, Zemedelska 1, 613 00 Brno, Czech Republic.
authors.forename: Vojtech
authors.initials: V
authors.lastname: Adam
authors.affiliation: Zentiva, k.s., Development Department, U Kabelovny 130, 102 37 Praha 10, Czech Republic.
authors.forename: Tomas
authors.identifier: 0000-0001-8296-509X
authors.initials: T
authors.lastname: Pekarek
authors.affiliation: Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1-3, 612 42 Brno, Czech Republic.
authors.forename: Josef
authors.identifier: 0000-0003-2003-9052
authors.initials: J
authors.lastname: Jampilek
authors.affiliation: Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1-3, 612 42 Brno, Czech Republic.
authors.forename: Petr
authors.identifier: 0000-0003-2389-2868
authors.initials: P
authors.lastname: Babula
mesh_terms: D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D059371:DNA, B-Form / Q000737:chemistry* / Q000378:metabolism; D009285:Naphthoquinones / Q000737:chemistry* / Q000378:metabolism; D010944:Plants / Q000737:chemistry / Q000378:metabolism; D017382:Reactive Oxygen Species / Q000378:metabolism; D064210:Secondary Metabolism; D013059:Spectrum Analysis, Raman
chemical_list: D059371:DNA, B-Form; D009285:Naphthoquinones; D017382:Reactive Oxygen Species; D004247:DNA; C005090:lawsone; C005134:juglone; C014758:plumbagin