Journal
CARBOHYDRATE POLYMERS
Volume 224, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carbpol.2019.115166
Keywords
Cyclodextrin derivatives; Guanosine; Inclusion complex; Molecular modeling; MCF-7 cells
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Funding
- National Research Foundation (NRF) of Korea - Ministry of Science, Information, and Communications Technology (MSIT) of the Korea Government [2017R1C1B5076345, 2017R1C1B5076286, 2018R1A2B2004432]
- Priority Research Centers Program [2014R1A6A1031189]
- Korean Ministry of Education, Science, and Technology [2012M3A7B4049675]
- National Research Foundation of Korea [2017R1C1B5076286] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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This study improves the water solubility and cellular uptake of guanosine (GuN) through an inclusion complexation with cyclodextrin derivatives (CDs), namely beta-cyclodextrin (beta-CD), hydroxypropyl-beta-cyclodextrin (HP-beta-CD), and sulfobutyl ether-beta-cyclodextrin (SBE-beta-CD). Inclusion complexes of GuN and CDs are synthesized in a 1:1 stoichiometric ratio with binding constants calculated using the Benesi-Hildebrand method. Characterizations of the prepared solid complexes using FTIR, XRD, TGA-DSC, and SEM indicate that GuN is found inside the cavity of the CDs. Moreover, in silico molecular modeling analysis identifies the most favorable binding interactions of GuN deeply encapsulated in the hydrophobic cavities of the CDs, as validated by PatchDock and FireDock servers. In addition, human breast cancer MCF-7 cell activity indicates that the SBE-beta-CD:GuN complex displays better cell viability and cellular uptake than GuN or other inclusion complexes of beta-CD:GuN and HP-beta-CD:GuN.
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