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Enhanced Cellular Uptake Of Phenamil Through Inclusion Complex With Histidine Functionalized beta-Cyclodextrin As Penetrative Osteoinductive Agent
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Enhanced Cellular Uptake Of Phenamil Through Inclusion Complex With Histidine Functionalized beta-Cyclodextrin As Penetrative Osteoinductive Agent
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Journal Article
Enhanced Cellular Uptake Of Phenamil Through Inclusion Complex With Histidine Functionalized beta-Cyclodextrin As Penetrative Osteoinductive Agent
2019
Overview
Background: Phenamil (PH) is a small molecule that induces bone formation through upregulation of the TRB3 gene in the bone-regeneration process. [beta]-Cyclodextrins ([beta]CDs) with hydrophilic surfaces and a relatively hydrophobic cavity can form inclusion complexes with primarily hydrophobic small molecules such as PH, and increase their apparent solubility and dissolution rate. The hydrophilic surface of [beta]CDs prevents their interaction with the hydrophobic lipids of the cell membrane for penetration. Therefore, binding of penetrative groups, such as lysine, arginine, and histidine (His), to [beta]CDs for cell penetration is required. Aim: The aim of this study was to investigate the effect of His-conjugated [beta]CD on cellular uptake of PH for bone differentiation. Methods: In this study, His-[beta]CDs were synthesized and used to prepare an inclusion complex of His-[beta]CD-PH. A hydroxypropyl-[beta]CD-PH (HP-[beta]CD-PH) inclusion complex for increasing PH solubility without a penetrative group was prepared for comparison. 3-D geometry of [beta]CD derivatives and PH-inclusion complexes was investigated by Fourier-transform infrared spectroscopy and molecular docking. Alizarin red staining and real-time PCR were performed to compare bone differentiation of His-[beta]CD-PH and HP-[beta]CD-PH. Results: The results suggested that the benzene ring of PH was inserted into the wide side of both His-[beta]CD and HP-[beta]CD. Alizarin red staining at 14 days postculture in the presence of His-[beta]CD-PH at total concentration of 50 [micro]M for PH showed that bone-matrix mineralization increased significantly compared with free PH and HP-[beta]CD-PH. Real-time PCR confirmed this result, and showed gene expression increased significantly (OPN 1.84-fold, OCN 1.69-fold) when stem cells were cultured with His-[beta]CD-PH. Conclusion: The overall results indicated that His-[beta]CD-PH is a promising carrier for osteoinductive PH with possible penetration ability and sustained release that reduces BMP2 consumption for differentiation of mesenchymal stem cells to bone tissue. Keywords: phenamil, [beta]-cyclodextrin, inclusion complex, histidine, cell penetration, bone regeneration
Publisher
Dove Medical Press Limited
Subject
