1,4-Naphthoquinones: Some Biological Properties and Application

Abstract

Over the past decade, a number of new 1,4-naphthoquinones have been isolated from natural sources and new 1,4-naphthoquinones with diverse structural features have been synthesized. Cardioprotective, antiischemic, hepatoprotective, neuroprotective and some other new properties were found for these compounds; their role in protecting against neurodegenerative diseases has been established. Their anti-inflammatory, antimicrobial and antitumor activities have been studied in more detail; new, previously unknown intracellular molecular targets and mechanisms of action have been discovered. Some compounds of this class are already being used as a medicinal drugs and some substances can be used as biochemical tools and probes for non-invasive detection of pathological areas in cells and tissues in myocardial infarction and neurodegenerative diseases using modern molecular imaging techniques.

Inspired by Sea Urchins: Warburg Effect Mediated Selectivity of Novel Synthetic Non-Glycoside 1,4-Naphthoquinone-6S-Glucose Conjugates in Prostate Cancer

“…Spinochromes are an important family of polyhydroxynaphthoquinone secondary metabolites which were found in various sea urchin species. Due to their chemical diversity and promising pharmacological properties, these compounds attract the attention of scientific community as a base for development of new drugs [15,16]. Thus, spinochromes have revealed anti-allergic, anti-hypertensive, anti-diabetic, anti-oxidant, anti-inflammatory, and cardioprotective properties (reviewed in [15,16]).…”

“…Due to their chemical diversity and promising pharmacological properties, these compounds attract the attention of scientific community as a base for development of new drugs [15,16]. Thus, spinochromes have revealed anti-allergic, anti-hypertensive, anti-diabetic, anti-oxidant, anti-inflammatory, and cardioprotective properties (reviewed in [15,16]). In general, biological effects of naphthoquinones are associated with generation of reactive oxygen species and modulation of redox signaling radical reactions [17] being either pro-or antioxidants or electrophiles [18].…”

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

“…The quinone ring contains a system of double bonds conjugated with carbonyl groups: it is easily susceptible to reduction, oxidation, and addition of O -, N -, and S -nucleophiles [ 10 , 11 ]. The high reactivity of naphthoquinones and the well-developed methods of its chemical modification make this group of compounds attractive for the profound development of new types of substances with high biological activity [ 12 ].…”

The Cellular and Molecular Determinants of Naphthoquinone-Dependent Activation of the Aryl Hydrocarbon Receptor

“…Naphthoquinones (NQ) are byproducts of polycyclic aromatic hydrocarbon (PAH) oxidation and photolysis reactions and have been identified in a wide variety of materials (i.e., botanicals, air pollutants, and biologics) [1][2][3][4][5][6]. Mechanistically, NQ act as redox cyclers to stimulate the generation of free radicals involved in diverse physiological and pathophysiological outcomes [1,2,7], such as DNA damage and alterations of vital metabolic pathways (i.e., cellular respiration).…”

“…Mechanistically, NQ act as redox cyclers to stimulate the generation of free radicals involved in diverse physiological and pathophysiological outcomes [1,2,7], such as DNA damage and alterations of vital metabolic pathways (i.e., cellular respiration). The ability of NQs to act as potent cytotoxic, antiproliferative, and antimicrobial agents has led to an interest in designing NQ-based anticancer agents [1][2][3][8][9][10][11] and 1,2-naphthoquinone (1,2-NQ) and 1,4-naphthoquinone (1, are considered particularly promising in this regard. Although 1,2-NQ and 1,4-NQ are structurally similar (Figure 1), differences in the position of the carbonyl groups have been shown to result in diverse The aryl hydrocarbon receptor (AhR) is a ligand-dependent transcription factor that regulates the expression of a wide variety of genes and it plays a pivotal role in a broad spectrum of biological, physiological and toxicological effects [14][15][16][17][18][19].…”