Abstract
Carbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. Pyrazine-functionalized carbazole derivative was constructed by coupling 2-amino-5-bromo-3-methylaminepyrazine (ABMAP) into 3 and 6 positions of the carbazole ring. Multi-experimental methods were used, e.g., potentiometric, spectroscopic (ATR, UV, XRD powder,1H and13C NMR), electrochemical (cyclic voltammetry), and optical techniques, to receive the complete structural analysis, physicochemical (pKa, logP) and biological profile of a new carbazole derivative with acronym 3,6-PIRAMICAR. The interaction ability of the compound studied with potential cellular targets like Calf Thymus DNA (CT-DNA), or Bovine Serum Albumin (BSA) were also taken into account. Experiments showed the existence of strong binding, but no DNA or BSA cleavage was observed. The comparative analyzes of compounds anti-Candida action clearly show pH-dependent antifungal activity of 3,6-PIRAMICAR, which was strongly stimulated in the acidic media. Surprisingly, the titled compound turn out to be much more effective (14 times by MIC50; 8 times by MIC; c.a. 4 times by MFC) against Candida krusei than fluconazole at pH 4.
Highlights
Carbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds
The protonation reaction of 3,6-PIRAMICARwas prepared in the mentioned conditions and registered spectrophotometrically as evidenced by the reversible change presented in Supplementary Informa-Scientific Reports | (2020) 10:11767 |
The complete structural, physicochemical and microbiological 3,6-PIRAMICARprofile together with its interactions ability against potent cellular targets were reported in details
Summary
Carbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. The development of new antifungal agents in clinical trials is problematic inferior to the incidence of drug resistance, and the available antifungal agents are restricted Their mechanisms are based on certain characteristics of the fungus in order to avoid biological similarities with the host[1]. The studies about high active DNA intercalators show the significance of the carbazole structural agents like planarity or a romaticity[11,12]. The first concept of the studies was to check the basic design structures assumptions to predict pharmaceuticals activity, like presented carbazole functionalized by pyrazines—our previous research objects. The pathogens were changed in tests based on the predicted similarity of unknown 3,6-PIRAMICARto pyrazine derivatives antifungal action (selectivity against Candida albicans) studied in our previous r esearch[15,16,17,18]. Antifungal activity and lack of antibacterial activity, on the other hand, can be an advantage because such compounds are more selective
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