Enhanced solubility of guanosine by inclusion complexes with cyclodextrin derivatives: Preparation, characterization, and evaluation

Sonaimuthu Mohandoss; Raji Atchudan; Thomas Nesakumar Jebakumar Immanuel Edison; Tapas Kumar Mandal; Subramanian Palanisamy; SangGuan You; Ayyakannu Arumugam Napoleon; Jae-Jin Shim; Yong Rok Lee

doi:10.1016/j.carbpol.2019.115166

Enhanced solubility of guanosine by inclusion complexes with cyclodextrin derivatives: Preparation, characterization, and evaluation

Carbohydr Polym. 2019 Nov 15:224:115166. doi: 10.1016/j.carbpol.2019.115166. Epub 2019 Aug 5.

Authors

Sonaimuthu Mohandoss¹, Raji Atchudan¹, Thomas Nesakumar Jebakumar Immanuel Edison¹, Tapas Kumar Mandal¹, Subramanian Palanisamy², SangGuan You², Ayyakannu Arumugam Napoleon³, Jae-Jin Shim¹, Yong Rok Lee⁴

Affiliations

¹ School of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongbuk-do 38541, Republic of Korea.
² Department of Marine Food Science and Technology, Gangneung-Wonju National University, 120 Gangneungdaehangno, Gangneung, Gangwon 25457, Republic of Korea.
³ Pharmaceutical Chemistry Laboratory, SAS, VIT University, Vellore, 632014, Tamil Nadu, India.
⁴ School of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongbuk-do 38541, Republic of Korea. Electronic address: yrlee@yu.ac.kr.

PMID: 31472864
DOI: 10.1016/j.carbpol.2019.115166

Abstract

This study improves the water solubility and cellular uptake of guanosine (GuN) through an inclusion complexation with cyclodextrin derivatives (CDs), namely β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD), and sulfobutyl ether-β-cyclodextrin (SBE-β-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-β-CD:GuN complex displays better cell viability and cellular uptake than GuN or other inclusion complexes of β-CD:GuN and HP-β-CD:GuN.

Keywords: Cyclodextrin derivatives; Guanosine; Inclusion complex; MCF-7 cells; Molecular modeling.