Partition coefficient of gamavuton-0 in different organic solvents and pH: Experimental study

Abstract

Gamavuton-0 (GVT-0) is a derivative of curcumin that is reported to have acted as a biological activity, such as anticancer, antioxidant, and anti-inflammation. As a new drug compound, a hydrophobic or lipophilic parameter like coefficient partition should be determined to study the penetration ability of the compound to the body's biological membranes. This study aims to determine the effectiveness of re-maceration on the purification of GVT-0, before the partition coefficient values determination of GVT-0, and determine the effect of pH and polarity index of organic solvent on the partition coefficient. This study was conducted in four stages: synthesis, purification, analysis of the purity, and partition coefficient determination. The partition coefficient of GVT-0 was conducted at different pH (ranging from 2 to 8) and two different organic solvents with different polarity indexes at the temperature of 37 °C. Synthesis was done by reaction between acetone and vanillin in the round bottle flask, as the reaction chamber was equipped with a water condenser. The purification process was carried out by the re-maceration method using hot distilled water. Then, purity was determined using Thin Layer Chromatography (TLC), melting point analysis, and FTIR. The determination of the partition coefficient was done using the shake flask method. The organic solvent used was chloroform and toluene. The purity analysis using TLC, melting point test, and FTIR proved that the GVT-0 compound used in this work is pure. These results show that pH affects the partition coefficient value. The partition coefficient increases from pH 2 to 4 and decreases from pH 6 to 8. The highest partition coefficient value is obtained at around pH 4–5 compared to pH 2 and 8. Also, the different solvents with different polarity indexes give different values of partition coefficient partition; a higher partition coefficient value was for a higher polarity solvent.