Electrochemical Investigation of Interactions between Potential DNA Targeted Compounds, 2,4-Di- and 2,3,4-Trisubstituted Benzimidazo[1,2-a]pyrimidines and Nucleic Acid

Abstract

The electrochemical aspects of interactions between DNA and two organic compounds are discussed herein. Potential DNA targeted compounds, 2-methyl-4-phenyl-benzo [4,5]imidazo[1,2-a]pyrimidine (c1) and 2,3,4-trimethyl-benzo[4,5]-imidazo[1,2-a]pyrimidine (c2), were synthesized and their cytotoxic and/or growth inhibitory effects were studied previously. Disposable sensor technology was used to explore the interaction between the compounds and nucleic acid, such as fish sperm DNA at the electrode surface and in the solution phase. The changes upon encountering oxidation signals of electroactive DNA base-guanine and these compounds were monitored electrochemically.

Voltammetric and Impedimetric Detection of Interaction Between Dacarbazine and Nucleic Acids

“…It can be concluded that DTIC was more effectively interacted with ssDNA than dsDNA, due to obtained higher decrease % at both DTIC and guanine oxidation signals. The decrease at the guanine signal obtained after interaction process may be attributed to the DTIC alkylating structure, which was delivering methyl group to purine bases of DNA (O6‐guanine; N7‐guanine) .…”

Electrochemical detection of DNA interaction with Mannich base derivatives by disposable graphite electrodes

“…This decrease in electrode response obtained after the interaction process was similar to the results in earlier reports related to DNA interaction of some anticancer drugs and DNA-targeted compounds. 14,25,26,35,36 It may be attributed to the intercalation of these Mannich bases into the base pairs of DNA. This phenomenon could be explained by the shielding of oxidizable groups of electroactive base guanine, 14,16.22 while the compounds can interact with the double helix of DNA at the electrode surface due to possible intercalation and/or alkylation mechanism.…”

“…In conclusion, the benefit of the electrochemical recognition of the interaction between each Mannich base (C1/C2/C3/C4) and DNA has been shown for the first time herein using a faster, more sensitive, and less laborious voltammetric technique with the advantages of disposable PGE technology. 14,16,37 The success of the PGE over existing carbon electrodes is because it is commercially available, practical and cost-effective in use, and has better reproducibility. The electrochemical method presented here is experimentally convenient and sensitive, requiring only small amounts of DNA or compounds.…”

“…14,16,37 The success of the PGE over existing carbon electrodes is because it is commercially available, practical and cost-effective in use, and has better reproducibility. The electrochemical method presented here is experimentally convenient and sensitive, requiring only small amounts of DNA or compounds.…”

Electrochemical Determination of the Effect of Caffeic Acid onto the Interaction between Idarubicin and DNA by Single‐use Disposable Electrodes

“…Belonging to the structural features of both the molecule and DNA, several molecules indicate more than a single interaction mode with DNA. Intercalation is the most common way to link directly and selectively . Intercalating occurs when an aromatic ring of the drug is embedded among the base pairs in nucleic acid duplex, which enhances the distance amid the base pairs .…”