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.

In vitro label‐free screening of chemotherapeutic drugs using Raman microspectroscopy: Towards a new paradigm of spectralomics

“…It should be noted that, PLSR over the high concentration range, up to 50 μM, (Figure A) results in a spectral profile which is similar to those of DOX and ACT (Figure ) exhibiting strong features at 785 cm −1 (DNA backbone O─P─O) and 813 cm −1 (RNA O─P─O phosphodiester band stretching), while regression over the lower concentration up to the IC 50 of 1.2 ± 0.2 μM showed a decrease in features at 728, 830 and 1425 cm −1 , related to DNA B form and an increase in features at 668 and 675 cm −1 , related to DNA A form, indicative of conformational changes due to partial transition of the DNA B form to DNA A form due to Cisp binding .…”

Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of Zea mays L. Coleoptile Segments

“…In addition, it was also found that juglone, lawsone and 1,4-naphthoquinone induced reactive oxygen species [38,41] and the subsequent programmed cell death [17]. Naphthoquinones are able to inhibit some enzymes and proteins and bind to DNA, thereby modifying its conformation [23,42,43].…”

“…This fact suggests that lawsone inhibits auxin-induced growth indirectly by producing reactive oxygen species (ROS) that then increase cytosol Ca 2+ , which is followed by an inhibition of the PM H + -ATPase activity [60,61,62,63,64]. It was also found that lawsone has the ability to bind to DNA, which leads to a nonspecific interaction and the transition of Β-DNA into an A-DNA conformation [43].…”

Gigantol from Dendrobium chrysotoxum Lindl. binds and inhibits aldose reductase gene to exert its anti-cataract activity: An in vitro mechanistic study

“…And, we used SERS to further research the mode of interaction between gigantol and the AR gene. Experimental studies in recent years showed that SERS allows the Raman scattering signal of the tested material enhancement 1014-1015 times, and 10 -7 M of DNA can also be detected (Yang M et al, 2016;Kim S et al, 2016;Li Y et al, 2016;Vaverkova et al, 2014). In this experiment, the SERS peaks of AR gene were greatly enhanced with the increasing amounts gigantol.…”