New Synthetic Quinoline (Qui) Derivatives as Novel Antioxidants and Potential HSA's Antioxidant Activity Modulators-Spectroscopic Studies

Molecules. 2022 Dec 30;28(1):320. doi: 10.3390/molecules28010320.

Abstract

The antioxidant activity of drugs, as well as the influence of drugs on the activity of endogenous antioxidant mechanisms in the human body is of great importance for the course of the disease and the treatment process. Due to the need to search for new therapeutic methods, the study of newly synthesized substances with potential therapeutic activity is necessary. This study aimed to designate some properties and characteristic parameters of new, synthetic quinoline three derivatives-1-methyl-3-allylthio-4-(4'-methylphenylamino)quinolinium bromide (Qui1), 1-methyl-3-allylthio-4-(3'-hydroxyphenylamino)quinolinium bromide (Qui2) as well as 1-methyl-3-allylthio-4-(4'-hydroxyphenylamino)quinolinium bromide (Qui3), including their antioxidant properties, as well as to analyse their activity as the potential modulators of Human Serum Albumin (HSA) antioxidant activity. In order to achieve the goal of the study, spectroscopic methods such as UV-Vis and circular dichroism (CD) spectroscopy have been used and based on the obtained data only slight and probably some surface interaction of quinoline derivatives (Qui1-Qui3) with HSA have been observed. The effect of Qui1-Qui3 on the HSA secondary structure was also insignificant. All analysed quinine derivatives have antioxidant activity against ABTS cation radical, in turn against DPPH radical, only Qui3 has noticeable antioxidant potential. The highest reduction potential by Qui3 as well as (Qui3 + HSA)complex has been shown. Qui3 mixed with HSA has mostly the synergistic effect against DPPH, ABTS and FRAP, while Qui1 and Qui2 in the presence of HSA mostly have a synergistic and additive effect towards ABTS, respectively. Based on the obtained results it can be concluded that Qui2 and Qui3 can be considered potential modulators of HSA antioxidant activity.

Keywords: HSA; antioxidants; quinine derivatives; spectroscopy.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Binding Sites
  • Bromides
  • Circular Dichroism
  • Dermatologic Agents*
  • Humans
  • Molecular Docking Simulation
  • Protein Binding
  • Quinolines* / chemistry
  • Quinolines* / pharmacology
  • Serum Albumin, Human / chemistry
  • Spectrometry, Fluorescence
  • Spectrum Analysis
  • Thermodynamics

Substances

  • Antioxidants
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Bromides
  • Serum Albumin, Human
  • Dermatologic Agents
  • Quinolines

Grants and funding

This research was funded by Grant PCN-2-012/K/2/F, PCN-1-022/K/2/F, PCN-2-030/K/2/F, PCN-2-010/N/2/F, PCN-2-011/K/2/F from the Medical University of Silesia, Poland.