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Re: Manuscript AAPSPT-D-14-00358
pH dependent complexation of hydroxypropyl-beta-cyclodextrin with chlorin e6
AAPS PharmSciTech
Abstract: The activity of chlorin e6 (Ce6) in photodynamic therapy of
cancers is significantly reduced by its propensity to aggregate. It was
postulated that disaggregation of Ce6 could be achieved with the use of
hydroxypropyl-beta-cyclodextrin (HP--CD). An initial phase solubility
study of Ce6 was conducted with various concentrations of HP--CD at
three different pH conditions, i.e. pH 3, pH 5 and pH 7. Increase in Ce6
solubility was observed, especially at pH 7, indicating formation of
inclusion complex between Ce6 and HP--CD. Solubility-induced
disaggregation of Ce6 was illustrated by fluorescence spectroscopy and
singlet oxygen generation studies. Interaction between Ce6 and HP--CD
was further demonstrated by solid-state characterization techniques such as
FTIR, DSC and XRD. Molecular simulation showed HP--CD-Ce6 interaction
through H-bond formation, which was in good agreement with the findings of
the thermodynamic studies conducted. The inclusion complex demonstrated
improved photodynamic efficacy through enhanced singlet oxygen generation
and phototoxicity on human oral squamous carcinoma cells. |
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