Synthesis, structure, antioxidant activity, and water solubility of trolox ion conjugates

Abstract

The interaction of trolox with ammonia, alkylamines of different classes, and amino derivatives of heterocyclic compounds, including nitroxyl radicals and alkaloids, led to the production of ammonium salts called ion conjugates (ICs). Five ICs were characterised by X-ray diffraction. This is the first time a wide range of ICs were made from trolox with amines, and ESI-MS data demonstrated they have the potential to generate pseudomolecular [(AB) + H] ions. For all obtained trolox ICs, a significant increase (1-3 orders of magnitude) in water solubility was achieved while retaining high antioxidant activity. ICs synthesised from two biologically active fragments may be used to create polyfunctional agents with varying solubility and bioavailability.

Design of Trolox Compounds as Antioxidant and Their Analysis Using Quantitative Structure Activity Relationship

“…This study's material was taken from the research of Yushkova et al (2017) in the form of 14 troloxderived compounds and their antioxidant activity.…”

“…A number of compounds in the training set are analyzed using multiple linear regression with the backward method to obtain several models of the relationship between the IC50 log with electronic and molecular descriptors. Of the several models produced, the model is chosen that meets the statistical parameters specified to be tested for validity such as r 2 , PRESS, SEE, and Fcalculate/Ftable with criteria r 2 > 0.64 [5], SEE <0.3 [19], Fcalculate / Ftable ≥ 1 [20]. Models that fit the criteria are then validated using test data sets.…”

“…Trolox (6-hydroxy-2,5,7,8-tetramethyl chromane-2carboxylic acid) is one of the most widely known antioxidants and is a phenolic compound with high antioxidant potential. Trolox is usually used as an antioxidant platform in the synthesis process [5,6]. Apart from being an antioxidant, trolox is also reported to be active as a multi-target agent in the treatment of Alzheimer's disease, neuroprotective agent, anticancer [7,8,9], anti-inflammatory [10], hypothermia [11], protection of Gamma-ray irradiation [12], anti blinking and anti bleaching [13], inhibits apoptosis [14], antidiabetic [15], prevents osteoclastogenesis [16], reduces cortical nerve injury [17].…”

The Effect of Trolox on Oxidative Stress Index and Nitric Oxide Levels

“…Trolox, which is a water-soluble vitamin E analogue, is a synthetic material. Having the hydrophilic carboxyl group instead of the hydrophobic phytyl group in vitamin E, trolox provides ease of operation in water-based environments as it is capable of penetrating the lipid membrane (Carlotti et al 2004;Yushkova et al, 2018). In vivo and in vitro studies show that trolox protects against cardiac ischemia-reperfusion injury (Sagach et al, 2002), reduces oxidative stress (Salgo and Pryor, 1996;Utrera and Estevez, 2013;Bai et al, 2014) and inhibits cancer metastasis (Lee et al, 2014) as well as being used in TEAC-based (trolox equivalent antioxidant capacity) antioxidant measurement methods as standard (Miller et al, 1993) and as a protective agent in cosmetic products (Carlotti et al 2004).…”

A Facile Solid-State Synthesis and Antimicrobial Activity Studies on Some Piperidone Derivatives

“…Nitrogen inserted heterocycle have a chief position in organic as well as in medicinal chemistry because of the useful properties of many members of these compounds. [1][2][3] Over the piperidine derivatives are one of the most widely studied class of heterocyclic compounds and have usual attention as a source of new and useful pharmaceuticals and biologically active compounds, Piperidone compounds possess important biological properties, including analgesic, 4 antioxidant, 5 antibacterial, 6 antituberculosis, 7 antifungal, 8 anti-inflammatory 9 and also anticancer. [10][11][12][13] Phenyl ring are substituted piperidone, display a number of exciting pharmacological possessions.…”