Tunable structure of chimeric isomaltomegalosaccharides with double α-(1 → 4)-glucosyl chains enhances the solubility of water-insoluble bioactive compounds

• Published in: Carbohydrate polymers 2023-11, Vol.319, p.121185-121185, Article 121185
• Main Authors: Lang, Weeranuch, Tagami, Takayoshi, Kumagai, Yuya, Tanaka, Seiya, Kang, Hye-Jin, Okuyama, Masayuki, Saburi, Wataru, Mori, Haruhide, Hira, Tohru, Lee, Chaehun, Isono, Takuya, Satoh, Toshifumi, Hara, Hiroshi, Kurokawa, Takayuki, Sakairi, Nobuo, Yuguchi, Yoshiaki, Kimura, Atsuo
• Format: Article
• Language: English
• Subjects: Amylose; Chimeric isomaltomegalosaccharides; Cyclodextrin glucanotransferase; Ibuprofen; Quercetin; Water solubility enhancement
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2023.121185

Isomaltomegalosaccharides with α-(1 → 4) and α-(1 → 6)-segments solubilize water-insoluble ligands since the former complexes with the ligand and the latter solubilizes the complex. Previously, we enzymatically synthesized isomaltomegalosaccharide with a single α-(1 → 4)-segment at the reducing end (S-IMS) by dextran dextrinase (DDase), but the chain length [average degree of polymerization (DP) ≤ 9] was insufficient for strong encapsulation. We hypothesized that the conjugation of longer α-(1 → 4)-segment afforded the promising function although DDase is incapable to do so. In this study, the cyclodextrin glucanotransferase-catalyzed coupling reaction of α-cyclodextrin to S-IMS synthesized a new α-(1 → 4)-segment at the nonreducing end (N-4S) of S-IMS to form D-IMS [IMS harboring double α-(1 → 4)-segments]. The length of N-4S was modulated by the ratio between α-cyclodextrin and S-IMS, generating N-4Ss with DPs of 7–50. Based on phase-solubility analysis, D-IMS-28.3/13/3 bearing amylose-like helical N-4S with DP of 28.3 displayed a water-soluble complex with aromatic drugs and curcumin. Small-angle X-ray scattering revealed the chain adapted to rigid in solution in which the radius of gyration was estimated to 2.4 nm. Furthermore, D-IMS with short N-4S solubilized flavonoids of less-soluble multifunctional substances. In our research, enzyme-generated functional biomaterials from DDase were developed to maximize the hydrophobic binding efficacy towards water-insoluble bioactive compounds. [Display omitted]