When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

Abstract

Structure, ionic forms, hydrophilic and non-cytotoxic character of 2-hydrazinopyrazine with stronger affinity to BSA than DNA were proved.

Low-Molecular Pyrazine-Based DNA Binders: Physicochemical and Antimicrobial Properties

“…It can be seen that both calculated values are negative, which indicates the hydrophilic character of 2Cl3HP. In addition, the values are all above that of 2HP [1]. A comparison analysis of logP values determined previously for 2HP (−0.468) and those found in the safety data sheet for 2Cl3HP (−0.935) suggested the introduction of a Cl atom instead of an H atom to the third position of the 2HP ring causes a change in logP value.…”

“…The dependence of [DNA]/(εa − εf) as a function of [DNA] was plotted to determine the actual binding constant value describing the specific type of interactions in the studied system (Figure 8B). Interestingly, it is also possible to perform a comparative analysis of the two typical low-molecular binders: 2HP [1] and 2Cl3HP. Based on their values of the binding constant, it can be concluded that 2Cl3HP interacts with DNA almost 1.65-fold stronger compared to 2HP.…”

“…The establishing of the binding mode of the small organic molecules with DNA is a promising research topic. Small molecules can bind with DNA through covalent or noncovalent interactions [1]. Studies focusing on deciphering the interactions occurring between a compound and DNA help us to better understand the mechanism of its action at the molecular level.…”

“…Pyrazine and its derivatives are a large group of compounds that exhibit broad biological activity, the changes of which can be easily detected by a substituent effect or a change in the functional group. Hence, 2-chloro-3-hydrazinopyrazine (2Cl3HP) is considered an interesting and promising research object compared with known pyrazinamide or the previously studied 2-hydrazinopyrazine (2HP) [1]. The important aim of research on compounds is to determine the interaction site in a living organism, and thus its molecular target.…”

“…Additionally, the DFT results will be compared with those acquired recently for 2hydrazinopyrazine (2HP) [1] to determine the relationships associated with the chloride substituent effect. A known antituberculosis drug, pyrazinamide (PZA), was used for comparison, and its interaction with DNA was studied as a reference [12,13].…”