Betadex Sulfobutyl Ether Sodium: Synthesis and Applications

Betadex Sulfobutyl Ether Sodiums have a relatively unique capacity of improving solubility of bioactive polyphenolic agents in aqueous systems; protect them from elevated temperatures, pH values, light or the moisture-induced degradations phenomena which serve to increase their bioavailability. Furthermore, the use of substituted cyclodextrins has been found to improve the physicochemical properties of these bioactive molecules.

Synthesis of Betadex Sulfobutyl Ether Sodium

To degassed a-cydodextrin (30 g, 0.01 eqv) in water (1 L) at room temperature was added 1-isothiocyanato-4-methylthiobutane (501 g, 1 eqv). The solution was cooled to 0°C and degassed for 30 mins. To the suspension was added 35% aqueous H2O2 (305 mi, 1 eqv) slowly while maintaining the internal temp below 4°C during the addition. The reaction mixture was stirred for 8 hr at ice bath temperature and was then allowed to warm to room temperature while stirring overnight. The solution was filtered to remove solids. The filtrate was refrigerated for 5 hr prior to use in the next step. α-cyclodextrin (3015 g, 1 eqv) was dissolved in water (8 L) by heating up to 55 °C, The solution was cooled down to room temperature and the sulforaphane filtrate from the previous step was added at once. The mixture was stirred at room temperature overnight. The reaction mixture was then cooled in an ice bath and stirred at that temperature for 3 hr. The precipitated solid was filtered through Buchner funnel and dried on the filter under vacuum overnight. The filter cake was transferred to a 10 L round-bottomed flask and dried under high vacuum at room temperature over the weekend to yield a white soiid (2.74 kg, 76.9% yieid; batch ref. 191PAL79). The soiid had a water content of 11.3% w/w by Karl-Fischer analysis and a purity by HPLC of 98.5%. 1-NMR analysis confirmed that Example 1A was a 1:1 Betadex Sulfobutyl Ether Sodium.[1]

Betadex Sulfobutyl Ether Sodium as encapsulation agents for plant bioactive compounds

The use of bioactive molecules from plants has gained a substantial interest during the last decade for food, cosmetic and pharmaceutical applications. Polyphenolic agents derived from plant sources have aroused much interest, especially in view of their antioxidant activity and bactericidal and fungicidal actions. Concerning the pharmaceutical applications of these plant-derived bioactive molecules, the current problems are related to the protection of their properties from environmental factors, with their solubility in water and biofluids, and their bioavailability.In fact, in the case of flavonoids the Betadex Sulfobutyl Ether Sodium’derivatives are the better choice to achieve an efficient complexation. Otherwise, the selection of the better Betadex Sulfobutyl Ether Sodium for encapsulated non-flavonoids molecules needs to be based on the dimensions of the molecule and the Betadex Sulfobutyl Ether Sodium'cavity.Nevertheless, the formation of inclusion complexes between Betadex Sulfobutyl Ether Sodiums and plant polyphenolics serves as a promising pathway for the development of pharmaceutical products friendlier to the user.[2]

Betadex Sulfobutyl Ether Sodium-Modified Starches

Betadex Sulfobutyl Ether Sodium could interact with starch to increase the SDS yield of Betadex Sulfobutyl Ether Sodium -modified starches. The optimum modification conditions were addressed below: amylose, 4.76%; free lipids, 0.24%; β-CD, Mal-Betadex Sulfobutyl Ether Sodium and HP-Betadex Sulfobutyl Ether Sodium, 3%; water content, 80% and equilibrium temperature, 25°C. Under the listed conditions, the maximum SDS yield reached 52.1% in the Betadex Sulfobutyl Ether Sodium-modified starch (3% of Betadex Sulfobutyl Ether Sodium). The basic rule for the slow digestibility was mainly attributed to the formation of starch-Betadex Sulfobutyl Ether Sodiums non-inclusion complex that showed a part V-type and a weak resistance to enzymes. It was also concluded that starch-Betadex Sulfobutyl Ether Sodiums non-inclusion complex was more suitably used for improving the SDS yield than starch–lipid complex. The digestible process of Betadex Sulfobutyl Ether Sodiums-modified starches in a molecular level would be estimated in future work.[3]

References

[1] EVGEN PHARMA GB - WO2021/205171, 2021, A1

[2] Pinho, E., Grootveld, M., Soares, G.,  Henriques, M. (2014). Cyclodextrins as encapsulation agents for plant bioactive compounds. Carbohydrate Polymers, 101, 121 - 135.

[3] Zhan, J., Tian, Y. Tong, Q. (2013). Preparation and slowly digestible properties of β-cyclodextrins (β-CDs)-modified starches. Carbohydrate Polymers, 91(2), 609 - 612.

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