Abstract
Betulin-3,28-diphosphate (BDP) obtained by phosphorylation of betulin using POCl3 has two main structural forms—BDP-1 and BDP-2—which differ in ethanol solubility, melting point, FTIR spectra, thermoanalytical characteristics and biological activity. Betulin-3,28-diphosphate and its sodium salt (Na-BDP) were characterized using 13C and 31P-NMR spectra, powder XRD experiments, as well as differential scanning calorimetry (DSC) and thermogravimetric analysis (TG) methods. The exo-effects at 193 ± 8 °C for ethanol soluble BDP-1 samples (−19.7 ± 0.2 kJ∙mol−1) were about three times less than for ethanol insoluble BDP-2 samples f (−70.5 ± 0.7 kJ∙mol−1). The DSC curves of Na-BDP-1 and Na-BDP-2 characterized the endo-effects having a maximum at 95–112 °C. Water-soluble Na-BDP-1 was obtained as needle-like crystals, unlike poorly crystalline Na-BDP-2, whereas BDP-1 and BDP-2 aged with time and were isolated as amorphous substances. In vitro experiments on rats showed that compared to the control, Na-BDP-1 increased catalase and SOD activity and improved energy metabolism more effectively than Na-BDP-2.
Highlights
Lupane-type triterpenoids such as betulinic and betulonic acids, betulin succinates, betulin acetates and other esters of organic acids, show antitumor, lipid-lowering, hepatoprotective and antiviral properties [1,2,3,4,5]
In this work we developed a synthesis of betulin-3,28-diphosphate (3β,28-diphosphatelup-20(29)-ene, BDP) and studied physicochemical properties and its sodium salt using potentiometry, differential scanning calorimetry (DSC)/thermogravimetric analysis (TG), FTIR and powder XRD analysis
The solubility, melting point, and FTIR spectra of betulin-3,28-diphosphate (BDP) samples having the same chemical composition depended on the methods of its synthesis, purification and storage conditions
Summary
Lupane-type triterpenoids such as betulinic and betulonic acids, betulin succinates, betulin acetates and other esters of organic acids, show antitumor, lipid-lowering, hepatoprotective and antiviral properties [1,2,3,4,5]. The therapeutic use of betulin derivatives is limited to their poor solubility (from 1 to 100 μg·L−1 ) and low bioavailability. One of the ways to improve bioavailability of betulin derivatives as the potential active pharmaceutical ingredients is the synthesis of their derivatives containing sulfate, sulfonate, phosphate and phosphonate groups [6,7,8]. Betulin-3,28-diphosphate has proved to be a broad-spectrum drug in vitro and in vivo studies [8,10,11,12]. It was shown that betulin-3,28-diphosphate can be an antibacterial agent [10], an effective antiviral and antifungal agent [8,11] as well as an inhibitor of complement system activation, which plays an important role in the treatment of many systemic diseases [12]
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